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Topical Collection "Bioactive Compounds"

Editors

Prof. Dr. Roberto Fabiani
Website
Collection Editor
Department of Chemistry, Biology and Biotechnology - University of Perugia, Via del Giochetto, 06126 Perugia, Italy
Interests: cancer chemoprevention; molecular nutrition; olive oil; polyphenols; phenolic compounds; natural bioactive compounds; antioxidants; oxidative stress; genotoxicity; mutagenicity; apoptosis; cell cycle regulation; DNA damage
Special Issues and Collections in MDPI journals
Dr. Eliana Pereira
Website
Collection Editor
Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
Interests: chemistry of natural product; emerging conservation technologies; development of functional food; recovery of biological waste; biobased ingredients
Special Issues and Collections in MDPI journals
Prof. Dr. Isabel C.F.R. Ferreira
Website
Former Collection Editor
Centro de Investigação de Montanha CIMO, Instituto Politécnico de Bragança, Campus de Santa Apolónia, P-5300253 Bragança, Portugal
Interests: food chemistry; natural products; functional foods
Special Issues and Collections in MDPI journals
Prof. Dr. Nancy D. Turner
Website
Former Collection Editor
Director, TAMU Space Life Sciences Mentored Research Program, Nutrition & Food Science Department, Texas A&M University, 2253 TAMU, 214C Cater Mattil, College Station, TX 77843-2253, USA
Interests: Nutrition, colon cancer, polyphenols, intestinal microbiota, apoptosis
Special Issues and Collections in MDPI journals

Topical Collection Information

Dear Colleagues,

Consumers increasingly believe that foods contribute directly to their health and well-being. In this context, extranutritional constituents that typically occur in small quantities in foods, "Bioactive compounds", play a very significant role. Bioactive compounds are being intensively studied to evaluate their effects on health, including antioxidant, antiallergic, antimicrobial, antithrombotic, antiatherogenic, hypoglycaemic, anti-inflammatory, antitumor, cytostatic, immunosuppressive properties, and hepatoprotective activities. Contributions for this issue, both in form of original research and review articles, may cover all aspects of bioactive compounds with proven activities in various biological screenings and pharmacological models, e.g. quantification, variability and efficacy of bioactive compounds; development of new protocols and methods based on chemical or biological systems for the evaluation of in vivo and in vitro bioactivity; clinical and nutritional trials focused on the bioactive properties of bioactive compounds synthesized or isolated; elucidation of bioactive compounds mechanisms; innovative techniques of bioactive compounds delivery and protocols for the extraction, isolation, structural characterization of new bioactive compounds will be welcomed, on condition that an adequate evaluation of their efficacy is provided. Papers regarding the development of pharmaceuticals from bioactive compounds will be also taken into consideration.

Prof. Dr. Roberto Fabiani
Dr. Eliana Pereira
Dr. Isabel C.F.R. Ferreira
Dr. Nancy D. Turner
Collection Editors

Manuscript Submission Information

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Keywords

  • bioactivity
  • natural products
  • synthesised compounds
  • isolation techniques
  • structure elucidation
  • mechanism of action

Related Special Issue

Published Papers (394 papers)

2020

Jump to: 2019, 2018, 2017, 2016, 2015, 2014, 2013, 2012, 2011, 2010

Open AccessArticle
Bioactivity-Guided Identification of Anti-Adipogenic Isothiocyanates in the Moringa (Moringa oleifera) Seed and Investigation of the Structure-Activity Relationship
Molecules 2020, 25(11), 2504; https://doi.org/10.3390/molecules25112504 (registering DOI) - 28 May 2020
Abstract
Due to the side effects of obesity medications, many studies have focused on the natural products used in the daily diet to control weight. Moringa seed pods and leaves are widely used as vegetables or diet supplements due to the high nutrition value. [...] Read more.
Due to the side effects of obesity medications, many studies have focused on the natural products used in the daily diet to control weight. Moringa seed pods and leaves are widely used as vegetables or diet supplements due to the high nutrition value. However, no bioactivity-guided anti-adipogenic study was previously conducted. Therefore, a preadipocyte cell line was adopted as the bioactivity assay to identify the anti-adipogenic compounds in the peeled Moringa seed. Two known sulphur-containing compounds (1 and 2) were isolated and identified. Compound 2, 4-(α-l-rhamnosyloxy) benzyl isothiocyanate, showed a great anti-adipogneic effect with an IC50 value of 9.2 μg/mL. The isothiocyanate (ITC) group in compound 2 could be responsible for the inhibitory activity. In addition, a series of compounds with the ITC group were used to further investigate the structure-activity relationship, indicating foods containing ITC derivatives have the potential of being used to control weight. Full article
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Open AccessArticle
Anti-Acne Action of Peptides Isolated from Burdock Root—Preliminary Studies and Pilot Testing
Molecules 2020, 25(9), 2027; https://doi.org/10.3390/molecules25092027 - 27 Apr 2020
Abstract
This work aimed to study the anti-bacterial, anti-biofilm and anti-oxidant potential effects of low molecular weight (LMW) peptides (Br-p) isolated from burdock (Arctium lappa L.) roots. We conducted a preliminary study to exclude or confirm the antibiotic activity of the LMW [...] Read more.
This work aimed to study the anti-bacterial, anti-biofilm and anti-oxidant potential effects of low molecular weight (LMW) peptides (Br-p) isolated from burdock (Arctium lappa L.) roots. We conducted a preliminary study to exclude or confirm the antibiotic activity of the LMW peptides fraction of this plant. Br-p were isolated using gel filtration and a 10 kDa cut-off membrane. The obtained peptides were identified by MALDI TOF/TOF. Antibacterial activity was tested against acne strains using diffusion tests, MIC and MBC. The fibroblast cytotoxicity of Br-p was tested, and the selectivity index (SI) value was determined. The fraction of 46 Br-p peptides isolated from burdock root with a molecular weight below 5000 Da and theoretic pI (isoelectric point) of 3.67–11.83 showed a narrow spectrum of activity against Gram-positive acne bacterial strains. One of the Br-p peptides assessed on MALDI RapidDeNovo was LRCDYGRFFASKSLYDPLKKRR cationic peptide. It was analogous to that contained in A. lappa protein, and theoretically it was matched as a peptide with antibiotic nature. Br-p did not show toxicity to fibroblasts in the tested concentration up to 10 mg/mL, obtaining CC50 10 mg/mL. The SI value for the tested Propionibacterium strains ranged from 160 to 320. Finally, an active dressing based on chitosan/alginate/genipin was prepared using freeze-drying. The formed dressing was evaluated for its anti-acne activity. To sum up: preliminary biological studies confirmed the anti-acne properties of the isolated peptide fraction from burdock root and pointed to the possibility of using it to create an active dressing on the skin. Full article
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Open AccessArticle
Profiling of Individual Desulfo-Glucosinolate Content in Cabbage Head (Brassica oleracea var. capitata) Germplasm
Molecules 2020, 25(8), 1860; https://doi.org/10.3390/molecules25081860 - 17 Apr 2020
Abstract
Individual glucosinolates (GSLs) were assessed to select cabbage genotypes for a potential breeding program. One hundred forty-six cabbage genotypes from different origins were grown in an open field from March to June 2019; the cabbage heads were used for GSL analyses. Seven aliphatics [...] Read more.
Individual glucosinolates (GSLs) were assessed to select cabbage genotypes for a potential breeding program. One hundred forty-six cabbage genotypes from different origins were grown in an open field from March to June 2019; the cabbage heads were used for GSL analyses. Seven aliphatics [glucoiberin (GIB), progoitrin (PRO), epi-progoitrin (EPI), sinigrin (SIN), glucoraphanin (GRA), glucoerucin (GER) and gluconapin (GNA)], one aromatic [gluconasturtiin (GNS)] and four indolyl GSLs [glucobrassicin (GBS), 4-hydroxyglucobrassicin (4HGBS), 4-methoxyglucobrassicin (4MGBS), neoglucobrassicin (NGBS)] were found this study. Significant variation was observed in the individual GSL content and in each class of GSLs among the cabbage genotypes. Aliphatic GSLs were predominant (58.5%) among the total GSLs, followed by indolyl GSL (40.7%) and aromatic GSLs (0.8%), showing 46.4, 51.2 and 137.8% coefficients of variation, respectively. GIB, GBS and NGBS were the most common GSLs found in all genotypes. GBS was the most dominant GSL, with an average value of 3.91 µmol g−1 (0.79 to 13.14 µmol g−1). SIN, GIB, PRO and GRA were the other major GSLs, showing average values of 3.45, 1.50, 0.77 and 0.62 µmol g−1, respectively. The genotypes with relatively high contents of GBS, SIN, GIB and GRA warrant detailed studies for future breeding programs since the hydrolysis products of these GSLs have several anti-cancer properties. Full article
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Open AccessArticle
The Metabolic Changes of Artesunate and Ursolic Acid on Syrian Golden Hamsters Fed with the High-Fat Diet
Molecules 2020, 25(6), 1392; https://doi.org/10.3390/molecules25061392 - 18 Mar 2020
Abstract
Artesunate was well known as an antimalarial drug. Our previous research found that it has hypolipidemia effects in rabbits fed with a high-fat diet, especially combined with ursolic acid. In this study, we reconfirmed the lipid-lowering effect of artesunate and ursolic acid in [...] Read more.
Artesunate was well known as an antimalarial drug. Our previous research found that it has hypolipidemia effects in rabbits fed with a high-fat diet, especially combined with ursolic acid. In this study, we reconfirmed the lipid-lowering effect of artesunate and ursolic acid in hamsters and analyzed the metabolic changes using gas chromatography time-of-flight mass spectrometry (GC/TOF MS). Compared with the model group, a variety of different metabolites of artesunate and ursolic acid, alone or in combination, were found and confirmed. These differential metabolites, including fatty acids, lipids, and amino acids, were involved in lipid metabolism, energy metabolism, and amino acid metabolism. It indicated that two agents of artesunate and ursolic acid could attenuate or normalize the metabolic transformation on these metabolic pathways. Full article
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Open AccessArticle
Anti-Adipogenic and Anti-Inflammatory Activities of (−)-epi-Osmundalactone and Angiopteroside from Angiopteris helferiana C.Presl
Molecules 2020, 25(6), 1337; https://doi.org/10.3390/molecules25061337 - 15 Mar 2020
Abstract
Angiopteris helferiana C.Presl is a gigantic fleshy-type fern, belonging to Marattiaceae family. In previous study, we reported the potent anti-adipogenic and anti-inflammatory activities of ethylacetate (EtOAc) and n-butanol (BuOH) fractions of methanol extract of rhizomes of A. helferiana. In continuation, in [...] Read more.
Angiopteris helferiana C.Presl is a gigantic fleshy-type fern, belonging to Marattiaceae family. In previous study, we reported the potent anti-adipogenic and anti-inflammatory activities of ethylacetate (EtOAc) and n-butanol (BuOH) fractions of methanol extract of rhizomes of A. helferiana. In continuation, in this study, we report the isolation, characterization, and bioactivity analysis of principle bioactive compounds in these fractions. (−)-epi-Osmundalactone (1) and angiopteroside (2) were isolated from EtOAc and BuOH fractions, respectively. The structures of these compounds were established on the basis of NMR spectroscopic data. The quantification study using UPLC revealed the contents of compounds 1 and 2 in the dried rhizome to be 1.54% and 3.2%, respectively. These compounds were evaluated for their anti-adipogenic and anti-inflammatory activities using 3T3-L1 and RAW 264.7 cells, respectively. Compound 1 (2.5 µg/mL) and 2 (20 µg/mL) inhibited the lipid production by 35% and 25%, respectively. Regarding the anti-inflammatory activity, compound 1 (5 µg/mL) inhibited the nitrite production by nearly 82%. In conclusion, the presence of potent anti-adipogenic and anti-inflammatory compounds in A. helferiana indicate its potential role in the use of herb-based treatment for obesity and other related diseases. Full article
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Open AccessArticle
The Protective Effect of the Polysaccharide Precursor, D-Isofloridoside, from Laurencia undulata on Alcohol-Induced Hepatotoxicity in HepG2 Cells
Molecules 2020, 25(5), 1024; https://doi.org/10.3390/molecules25051024 - 25 Feb 2020
Abstract
Alcoholic liver disease (ALD) threatens human health, so it is imperative that we find ways to prevent or treat it. In recent years, the study of polysaccharides has shown that they have different kinds of bioactivities. Among them are many biological effects that [...] Read more.
Alcoholic liver disease (ALD) threatens human health, so it is imperative that we find ways to prevent or treat it. In recent years, the study of polysaccharides has shown that they have different kinds of bioactivities. Among them are many biological effects that have been attributed to polysaccharide precursors. D-Isofloridoside (DIF) is one of the polysaccharide precursors from the marine red alga Laurencia undulata. This study evaluated the effect of DIF on alcohol-induced oxidative stress in human hepatoma cells (HepG2). As a result, DIF attenuated alcohol-induced cytotoxicity, reduced the amount of intracellular reactive oxygen species (ROS), and effectively reduced alcohol-induced DNA damage in HepG2 cells. In addition, a western blot showed that, after DIF treatment, the expression levels of glutathione (GSH), superoxide dismutase (SOD), and B-cell lymphoma-2 (bcl-2) increased, while the expression levels of γ-glutamyl transferase (GGT), BCL2-associated X (bax), cleaved caspase-3, and mitogen-activated protein kinase (p38 and c-Jun N-terminal kinase) signal transduction proteins reduced. This showed that DIF may protect cells by reducing the amount of intracellular ROS and inhibiting intracellular oxidative stress and apoptotic processes. Finally, molecular docking demonstrated that DIF can bind to SOD, GGT, B-cell lymphoma-2, and bax proteins. These results indicated that DIF can protect HepG2 cells from alcohol-induced oxidative stress damage, making it an effective potential ingredient in functional foods. Full article
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Open AccessArticle
Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus Fusarium sp. QF001 from the Roots of Scutellaria baicalensis
Molecules 2020, 25(4), 923; https://doi.org/10.3390/molecules25040923 - 19 Feb 2020
Abstract
The filamentous fungal pathogen Fusarium sp. causes several crop diseases. Some Fusarium sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, Fusarium sp. QF001, isolated from the inner rotten part of old roots of [...] Read more.
The filamentous fungal pathogen Fusarium sp. causes several crop diseases. Some Fusarium sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, Fusarium sp. QF001, isolated from the inner rotten part of old roots of Scutellariae baicalensis resulted in the isolation of two new photosensitive geometrical isomers of lucilactaene (compounds 2 and 3) along with lucilactaene (6) and six other known compounds (fusarubin (1), (+)-solaniol (4), javanicin (5), 9-desmethylherbarine (7), NG391 (8) and NG393 (9)). Newly isolated isomers and lucilactaene were unstable under light at room temperature and tended to be a mixture in equilibrium state when exposed to a polar protic solvent during reversed phase chromatography. Normal phase chromatography under dim light conditions with an aprotic mobile phase led to the successful isolation of the relatively unstable isomers 2 and 3. Their structures were elucidated as 8(Z)-lucilactaene (2) and 4(Z)-lucilactaene (3) based on spectroscopic data. The absolute configuration of 4 was speculated to be R by computer-assisted specific rotation analysis. The isolated compounds could inhibit NO production and suppress pro-inflammatory cytokines expression in LPS-stimulated macrophage cells. These properties of the isolated compounds indicate their potential use as anti-inflammatory drugs. Full article
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Open AccessReview
A Review of Biologically Active Natural Products from Mediterranean Wild Edible Plants: Benefits in the Treatment of Obesity and Its Related Disorders
Molecules 2020, 25(3), 649; https://doi.org/10.3390/molecules25030649 - 03 Feb 2020
Abstract
Wild foods constitute an essential component of people’s diets around the world. According to the Food and Agriculture Organization (FAO), over 100 million people in the EU consume wild foods, while 65 million collect some form of wild food themselves. The Mediterranean basin [...] Read more.
Wild foods constitute an essential component of people’s diets around the world. According to the Food and Agriculture Organization (FAO), over 100 million people in the EU consume wild foods, while 65 million collect some form of wild food themselves. The Mediterranean basin is a biodiversity hotspot of wild edible species. Nowadays, due to the renewed interest in alimurgic plants and the recent findings on the beneficial role of their phytochemical constituents, these species have been defined as “new functional foods”. Research on natural products has recently regained importance with the growing understanding of their biological significance. Botanical food supplements marketed for weight and fat loss in obese subjects will be one of the most important items in marketed nutraceuticals. The aim of this report was to review the phytochemical compounds of Mediterranean wild edible species and their therapeutic potential against obesity and its related disorders. Results on the in vitro and in vivo activity of the most interesting plant extracts and their bioactive components are presented and discussed. The most interesting discoveries on their mechanisms of action are reported as well. Overall, this contribution highlights the importance and beneficial health roles of wild edible species. Full article
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Open AccessArticle
Naphthoquinone Derivatives with Anti-Inflammatory Activity from Mangrove-Derived Endophytic Fungus Talaromyces sp. SK-S009
Molecules 2020, 25(3), 576; https://doi.org/10.3390/molecules25030576 - 29 Jan 2020
Abstract
Twelve 1, 4-naphthoquinone derivatives, including two new (1 and 2) and 10 known (312), were obtained from endophytic fungus Talaromyces sp. SK-S009 isolated from the fruit of Kandelia obovata. All structures were identified through extensive analysis [...] Read more.
Twelve 1, 4-naphthoquinone derivatives, including two new (1 and 2) and 10 known (312), were obtained from endophytic fungus Talaromyces sp. SK-S009 isolated from the fruit of Kandelia obovata. All structures were identified through extensive analysis of the nuclear magnetic resonance (NMR), mass spectrometry (MS) and circular dichroism (CD), as well as by comparison with literature data. These compounds significantly inhibited the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in the murine macrophage cell line (RAW 264.7 cells). The half maximal inhibitory concentration (IC50) values, except for compound 2, were lower than that of indomethacin (26.3 μM). Compound 9 inhibited the LPS-induced inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNA expressions in RAW 264.7 macrophages. Additionally, compound 9 reduced the mRNA levels of pro-inflammatory factors interleukin (IL)1β, IL-6, and tumor necrosis factor (TNF)-α. The results of this study demonstrated that these 1, 4-naphthoquinone derivatives can inhibit LPS-induced inflammation. Full article
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Open AccessArticle
Pestalotiones A–D: Four New Secondary Metabolites from the Plant Endophytic Fungus Pestalotiopsis Theae
Molecules 2020, 25(3), 470; https://doi.org/10.3390/molecules25030470 - 22 Jan 2020
Cited by 1
Abstract
Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3 [...] Read more.
Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively. Full article
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Open AccessArticle
Effects of Orange Extracts on Longevity, Healthspan, and Stress Resistance in Caenorhabditis elegans
Molecules 2020, 25(2), 351; https://doi.org/10.3390/molecules25020351 - 15 Jan 2020
Abstract
Orange, with various bioactive phytochemicals, exerts various beneficial health effects, including anti-cancer, antioxidant, and anti-inflammatory properties. However, its anti-aging effects remain unclear. In this study, the Caenorhabditis elegans (C. elegans) model was used to evaluate the effects of orange extracts on [...] Read more.
Orange, with various bioactive phytochemicals, exerts various beneficial health effects, including anti-cancer, antioxidant, and anti-inflammatory properties. However, its anti-aging effects remain unclear. In this study, the Caenorhabditis elegans (C. elegans) model was used to evaluate the effects of orange extracts on lifespan and stress resistance. The results indicated that orange extracts dose-dependently increased the mean lifespan of C. elegans by 10.5%, 18.0%, and 26.2% at the concentrations of 100, 200, and 400 mg/mL, respectively. Meanwhile, orange extracts promoted the healthspan by improving motility, and decreasing the accumulation of age pigment and intracellular reactive oxygen species (ROS) levels without damaging fertility. The survival rates of orange extract-fed worms were obviously higher than those of untreated worms against thermal and ultraviolet-B (UV-B) stress. Moreover, the activities of superoxide dismutase (SOD) and catalase (CAT) were significantly enhanced while malondialdehyde (MDA) contents were diminished. Further investigation revealed that worms supplemented with orange extracts resulted in upregulated levels of genes, including daf-16, sod-3, gst-4, sek-1, and skn-1, and the downregulation of age-1 expression. These findings revealed that orange extracts have potential anti-aging effects through extending the lifespan, enhancing stress resistance, and promoting the healthspan. Full article
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2019

Jump to: 2020, 2018, 2017, 2016, 2015, 2014, 2013, 2012, 2011, 2010

Open AccessCommunication
An Autophagy Inducing Triterpene Saponin Derived from Aster koraiensis
Molecules 2019, 24(24), 4489; https://doi.org/10.3390/molecules24244489 - 07 Dec 2019
Abstract
Autophagy is an important self-degradative mechanism that plays a key role in treating neurodegeneration diseases. This research aimed at discovering bioactive compounds from Aster koraiensis. A new triterpene saponin, astersaponin I (1), was isolated from the EtOH extract of A. [...] Read more.
Autophagy is an important self-degradative mechanism that plays a key role in treating neurodegeneration diseases. This research aimed at discovering bioactive compounds from Aster koraiensis. A new triterpene saponin, astersaponin I (1), was isolated from the EtOH extract of A. koraiensis. The structure of 1 was characterized by spectroscopic methods, ECD calculation, and acid hydrolysis. The biochemical analysis showed that compound 1 significantly increased the expression of microtubule-associated protein 1A/1B light chain 3B (LC3-II) expression in SH-SY5Y cells, which indicates the induction of autophagy. Thus, further study may be needed to clarify whether compound 1 exerts beneficial effects on neurodegeneration diseases like Parkinson’s disease through autophagy induction. Full article
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Open AccessReview
The Genus Nerine Herb. (Amaryllidaceae): Ethnobotany, Phytochemistry, and Biological Activity
Molecules 2019, 24(23), 4238; https://doi.org/10.3390/molecules24234238 - 21 Nov 2019
Abstract
Nerine Herbert, family Amaryllidaceae, is a genus of about 30 species that are native to South Africa, Botswana, Lesotho, Namibia, and Swatini (formerly known as Swaziland). Species of Nerine are autumn-flowering, perennial, bulbous plants, which inhabit areas with summer rainfall and cool, dry [...] Read more.
Nerine Herbert, family Amaryllidaceae, is a genus of about 30 species that are native to South Africa, Botswana, Lesotho, Namibia, and Swatini (formerly known as Swaziland). Species of Nerine are autumn-flowering, perennial, bulbous plants, which inhabit areas with summer rainfall and cool, dry winters. Most Nerine species have been cultivated for their elegant flowers, presenting a source of innumerable horticultural hybrids. For many years, species of Nerine have been subjected to extensive phytochemical and pharmacological investigations, which resulted in either the isolation or identification of more than fifty Amaryllidaceae alkaloids belonging to different structural types. Amaryllidaceae alkaloids are frequently studied for their interesting biological properties, including antiviral, antibacterial, antitumor, antifungal, antimalarial, analgesic, cytotoxic, and cholinesterase inhibition activities. The present review aims to summarize comprehensively the research that has been reported on the phytochemistry and pharmacology of the genus Nerine. Full article
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Open AccessReview
Mushrooms of the Genus Ganoderma Used to Treat Diabetes and Insulin Resistance
Molecules 2019, 24(22), 4075; https://doi.org/10.3390/molecules24224075 - 11 Nov 2019
Cited by 1
Abstract
Pharmacotherapy using natural substances can be currently regarded as a very promising future alternative to conventional therapy of diabetes mellitus, especially in the case of chronic disease when the body is no longer able to produce adequate insulin or when it cannot use [...] Read more.
Pharmacotherapy using natural substances can be currently regarded as a very promising future alternative to conventional therapy of diabetes mellitus, especially in the case of chronic disease when the body is no longer able to produce adequate insulin or when it cannot use the produced insulin effectively. This minireview summarizes the perspectives, recent advances, and major challenges of medicinal mushrooms from Ganoderma genus with reference to their antidiabetic activity. The most active ingredients of those mushrooms are polysaccharides and triterpenoids. We hope this review can offer some theoretical basis and inspiration for the mechanism study of the bioactivity of those compounds. Full article
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Open AccessArticle
Investigation on the Antifungal Ingredients of Saccharothrix Yanglingensis Hhs.015, an Antagonistic Endophytic Actinomycete Isolated from Cucumber Plant
Molecules 2019, 24(20), 3686; https://doi.org/10.3390/molecules24203686 - 13 Oct 2019
Abstract
Apple tree canker infected by Valsa mali var. mali is a serious and widely distributed disease in China. Saccharothrix yanglingensis Hhs.015 is an endophytic actinomycete isolated from cucumber roots, and it has been proven that this strain is a promising biocontrol agent on [...] Read more.
Apple tree canker infected by Valsa mali var. mali is a serious and widely distributed disease in China. Saccharothrix yanglingensis Hhs.015 is an endophytic actinomycete isolated from cucumber roots, and it has been proven that this strain is a promising biocontrol agent on apple tree canker in previous studies. The aim of this study was to elucidate the active ingredients in its metabolites. Two pentaene macrolides, WH01 and WH02, were isolated from strain Hhs.015, and their structures were elucidated based on the extensive spectroscopic analysis. WH01 and WH02 were identified as fungichromin and 1′-deoxyfungichromin, among which WH02 is a novel compound. These two compounds showed strong in vitro and in vivo antifungal activity against V. mali. By comparison of the structures of hyphae cells treated by pure compound and fermentation broth, it has been proven that pentaene macrolides are the main active ingredients in the metabolites of strain Hhs.015. This is the first report on the antifungal activity of fungichromin and its analogs on V. mali, and the 28-member pentaene macrolides were also firstly isolated from the genus of Saccharothrix. Full article
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Open AccessArticle
Characterization, Antioxidant, Anti-Aging and Organ Protective Effects of Sulfated Polysaccharides from Flammulina velutipes
Molecules 2019, 24(19), 3517; https://doi.org/10.3390/molecules24193517 - 28 Sep 2019
Abstract
As an irreversible and complex degenerative physiological process, the treatment for aging seems strategically necessary, and polysaccharides play important roles against aging owing to their abundant bioactivities. In this paper, the antioxidant and anti-aging activities of Flammulina velutipes polysaccharides (FPS) and its sulfated [...] Read more.
As an irreversible and complex degenerative physiological process, the treatment for aging seems strategically necessary, and polysaccharides play important roles against aging owing to their abundant bioactivities. In this paper, the antioxidant and anti-aging activities of Flammulina velutipes polysaccharides (FPS) and its sulfated FPS (SFPS) on d-galactose-induced aging mice were investigated. The in vitro antioxidant activities demonstrated that SFPS had strong reducing power and superior scavenging effects on 2, 2-diphenylpicrylhydrazyl (DPPH), hydroxyl radicals and the chelating activities of Fe2+. The in vivo animal experiments manifested that the SFPS showed superior antioxidant and protective abilities against the d-galactose-induced aging by increasing the antioxidant enzyme activities, decreasing lipid peroxidation, improving the inflammatory response and ameliorating the anile condition of mice. Furthermore, the structural analysis of SFPS was investigated through FT-IR, NMR, and HPLC analysis, and the results indicated that SFPS was a homogeneous heteropolysaccharide with a weight-average molecular weight of 2.81 × 103 Da. Furthermore, SFPS has also changed in characteristic functional groups and monosaccharide composition compared to FPS. These results suggested that sulfated modification could enhance the anti-oxidation, anti-aging and protective activities of F. velutipes polysaccharides, which may provide references for the development of functional foods and natural medicines. Full article
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Open AccessArticle
Accramycin A, A New Aromatic Polyketide, from the Soil Bacterium, Streptomyces sp. MA37
Molecules 2019, 24(18), 3384; https://doi.org/10.3390/molecules24183384 - 17 Sep 2019
Cited by 5
Abstract
Drug-like molecules are known to contain many different building blocks with great potential as pharmacophores for drug discovery. The continued search for unique scaffolds in our laboratory led to the isolation of a novel Ghanaian soil bacterium, Streptomyces sp. MA37. This strain [...] Read more.
Drug-like molecules are known to contain many different building blocks with great potential as pharmacophores for drug discovery. The continued search for unique scaffolds in our laboratory led to the isolation of a novel Ghanaian soil bacterium, Streptomyces sp. MA37. This strain produces many bioactive molecules, most of which belong to carbazoles, pyrrolizidines, and fluorinated metabolites. Further probing of the metabolites of MA37 has led to the discovery of a new naphthacene-type aromatic natural product, which we have named accramycin A 1. This molecule was isolated using an HPLC-photodiode array (PDA) guided isolation process and MS/MS molecular networking. The structure of 1 was characterized by detailed analysis of LC-MS, UV, 1D, and 2D NMR data. Preliminary studies on the antibacterial properties of 1 using Group B Streptococcus (GBS) produced a minimum inhibitory concentration (MIC) of 27 µg/mL. This represents the first report of such bioactivity amongst the naphthacene-type aromatic polyketides, and also suggests the possibility for the further development of potent molecules against GBS based on the accramycin scaffold. A putative acc biosynthetic pathway for accramycin, featuring a tridecaketide-specific type II polyketide synthase, was proposed. Full article
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Open AccessArticle
Antioxidant Effect of Extracts from Native Chilean Plants on the Lipoperoxidation and Protein Oxidation of Bovine Muscle
Molecules 2019, 24(18), 3264; https://doi.org/10.3390/molecules24183264 - 07 Sep 2019
Abstract
The present study investigated the antioxidant potential and the ability to inhibit lipid and protein oxidation in bovine meat of four native Chilean species: canelo (Drimys winteri), nalca (Gunnera tinctoria), tiaca (Caldcluvia paniculata), and ulmo (Eucryphia [...] Read more.
The present study investigated the antioxidant potential and the ability to inhibit lipid and protein oxidation in bovine meat of four native Chilean species: canelo (Drimys winteri), nalca (Gunnera tinctoria), tiaca (Caldcluvia paniculata), and ulmo (Eucryphia cordifolia). Phenolic acids (gallic, chlorogenic, caffeic, and coumaric) and flavonoids (catechin, epicatechin, and rutin) were identified and quantified by HPLC-MS/MS. Drimys winteri extract exhibited the highest antioxidant capacity evaluated by oxygen radical absorption capacity-red pyrogallol method (ORAC-PGR) and ferric ion reducing antioxidant power (FRAP) assays. All extracts decreased lipid oxidation induced by 2,2’-azo-bis(2-amidinopropane) dihydrochloride (AAPH) derived peroxyl radicals by anywhere between 30% and 50% the. In addition, canelo and nalca extracts decreased spontaneous oxidation by around 57% and 37% in relation to the control group, being even more efficient than butylated hydroxyanisole (BHT) a synthetic antioxidant. Protein oxidation in the myofibrillar proteins was evaluated by the formation of protein carbonyls and loss of protein thiols. The canelo, ulmo, and nalca extracts decreased the formation of carbonyls by around 30%. Plant extracts and BHT did not show an antioxidant effect on protein thiol loss. However, tiaca and ulmo extracts exerted a pro-oxidant effect, favoring the oxidation of sulfhydryl groups. The oxidizing system induced structural changes in myofibrillar protein (SDS−PAGE). A protective effect on protein structure from the canelo extract can be observed during the incubation when compared to samples incubated with AAPH. Full article
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Open AccessCommunication
New Sesquiterpenoids from the Fermented Broth of Termitomyces albuminosus and Their Anti-Acetylcholinesterase Activity
Molecules 2019, 24(16), 2980; https://doi.org/10.3390/molecules24162980 - 16 Aug 2019
Cited by 1
Abstract
Termitomyces albuminosus is the symbiotic edible mushroom of termites and cannot be artificially cultivated at present. In the project of exploring its pharmaceutical metabolites by microbial fermentation, four new selinane type sesquiterpenoids—teucdiol C (1), D (2), E (3 [...] Read more.
Termitomyces albuminosus is the symbiotic edible mushroom of termites and cannot be artificially cultivated at present. In the project of exploring its pharmaceutical metabolites by microbial fermentation, four new selinane type sesquiterpenoids—teucdiol C (1), D (2), E (3), and F (4), together with two known sesquiterpenoids teucdiol B (5) and epi-guaidiol A (6)—were obtained from its fermented broth of T. albuminosus. Their structures were elucidated by the analysis of NMR data, HR Q-TOF MS spectral data, CD, IR, UV, and single crystal X-ray diffraction. Epi-guaidiol A showed obvious anti-acetylcholinesterase activity in a dose-dependent manner. The experimental results displayed that T. albuminosus possess the pharmaceutical potential for Alzheimer’s disease, and it was an effective way to dig new pharmaceutical agent of T. albuminosus with the microbial fermentation technique. Full article
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Open AccessArticle
Differences in the Moisture Capacity and Thermal Stability of Tremella fuciformis Polysaccharides Obtained by Various Drying Processes
Molecules 2019, 24(15), 2856; https://doi.org/10.3390/molecules24152856 - 06 Aug 2019
Cited by 3
Abstract
We compared the proportions and differences in the polysaccharides of Tremella fuciformis (Berkeley) after drying them by various processes, such as 18 °C cold air, 50 °C hot air, and freeze-drying. We also focused on the moisture capacity kinetic parameters of Tremella fuciformis [...] Read more.
We compared the proportions and differences in the polysaccharides of Tremella fuciformis (Berkeley) after drying them by various processes, such as 18 °C cold air, 50 °C hot air, and freeze-drying. We also focused on the moisture capacity kinetic parameters of Tremella fuciformis polysaccharides using various thermal analyses, including differential scanning calorimetry and thermogravimetric techniques. Erofeev’s kinetic and proto-kinetic equations, utilized for kinetic model simulation, can predict the moisture capacity due to the thermal effect. Among the various drying processes, cold air-drying had the highest molecular weight of 2.41 × 107 Da and a moisture content of 13.05% for Tremella fuciformis polysaccharides. Overall, the freeze-dried products had the best thermal decomposition properties under the conditions of a closed system, with an air or nitrogen atmosphere, and had an excellent moisture capacity of around 35 kJ/kg under a closed system for all samples. Full article
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Open AccessArticle
Phytotoxic Activity and Structure–Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)
Molecules 2019, 24(15), 2793; https://doi.org/10.3390/molecules24152793 - 31 Jul 2019
Cited by 2
Abstract
Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (25), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass [...] Read more.
Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (25), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass (Cenchrus ciliaris), an invasive weed in North America. Among the different metabolites 1 showed target-specific activity against the host plant and no toxicity on zebrafish embryos, promoting its potential use to develop a natural bioherbicide formulation to manage buffelgrass. These data and the peculiar structural feature of 1 suggested to carry out a structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization and the activity by leaf puncture bioassay against buffelgrass of all the derivatives is reported. Most of the compounds showed phytotoxicity but none of them had comparable or higher activity than radicinin. Thus, the presence of an α,β unsaturated carbonyl group at C-4, as well as, the presence of a free secondary hydroxyl group at C-3 and the stereochemistry of the same carbon proved to be the essential feature for activity. Full article
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Open AccessArticle
The Antioxidant and Anti-Aging Effects of Acetylated Mycelia Polysaccharides from Pleurotus djamor
Molecules 2019, 24(15), 2698; https://doi.org/10.3390/molecules24152698 - 24 Jul 2019
Cited by 1
Abstract
The present work mainly describes the preparation of acetylated mycelia polysaccharides (AMPS) from Pleurotus djamor and investigates the antioxidant and anti-aging effects in d-galactose-induced aging mice. The optimized procedure indicates the acetyl substitution degree of AMPS is 0.54 ± 0.04 under the [...] Read more.
The present work mainly describes the preparation of acetylated mycelia polysaccharides (AMPS) from Pleurotus djamor and investigates the antioxidant and anti-aging effects in d-galactose-induced aging mice. The optimized procedure indicates the acetyl substitution degree of AMPS is 0.54 ± 0.04 under the conditions of a reaction time of 56 h, a reaction temperature of 37 °C, and 4 mL of added acetic anhydride. The in vitro analysis and in vivo animal experiments indicate that the AMPS could alleviate the aging properties by scavenging the radicals, elevating the enzyme activities, and reducing the lipid contents. As for serum levels, the AMPS can improve the serum biochemical indices and enhance immunological activity. The histopathological observations indicate that the injuries to the liver, kidney, and brain can be remitted by AMPS intervention. The characterization showed that AMPS was one kind of β-pyranose with the weight-average molecular weights of 3.61 × 105 Da and the major monosaccharides of mannose and glucose. The results suggest that AMPS can be used as a dietary supplement and functional food for the prevention of aging and age-related diseases. Full article
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Open AccessArticle
The Antiglycoxidative Ability of Selected Phenolic Compounds—An In Vitro Study
Molecules 2019, 24(15), 2689; https://doi.org/10.3390/molecules24152689 - 24 Jul 2019
Cited by 4
Abstract
Hyperglycemia and oxidative stress may be observed in different diseases as important factors connected with their development. They often occur simultaneously and are considered together as one process: Glycoxidation. This can influence the function or structure of many macromolecules, for example albumin, by [...] Read more.
Hyperglycemia and oxidative stress may be observed in different diseases as important factors connected with their development. They often occur simultaneously and are considered together as one process: Glycoxidation. This can influence the function or structure of many macromolecules, for example albumin, by changing their physiological properties. This disturbs the homeostasis of the organism, so the search for natural compounds able to inhibit the glycoxidation process is a current and important issue. The aim of this study was the examination of the antiglycoxidative capacity of 16 selected phenolic compounds, belonging to three phenolic groups, as potential therapeutic agents. Their antiglycoxidative ability, in two concentrations (2 and 20 µM), were examined by in vitro study. The inhibition of the formation of both glycoxidative products (advanced glycation end products (AGEs) and advanced oxidation protein products (AOPPs)) were assayed. Stronger antiglycoxidative action toward the formation of both AOPPs and AGEs was observed for homoprotocatechuic and ferulic acids in lower concentrations, as well as catechin, quercetin, and 8-O-methylurolithin A in higher concentrations. Homoprotocatechuic acid demonstrated the highest antiglycoxidative capacity in both examined concentrations and amongst all of them. A strong, significant correlation between the percentage of AOPPs and AGEs inhibition by compounds from all phenolic groups, in both examined concentrations, was observed. The obtained results give an insight into the antiglycoxidative potential of phenolic compounds and indicate homoprotocatechuic acid to be the most promising antiglycoxidative agent, but further biological and pharmacological studies are needed. Full article
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Open AccessArticle
Solidago graminifolia L. Salisb. (Asteraceae) as a Valuable Source of Bioactive Polyphenols: HPLC Profile, In Vitro Antioxidant and Antimicrobial Potential
Molecules 2019, 24(14), 2666; https://doi.org/10.3390/molecules24142666 - 23 Jul 2019
Cited by 4
Abstract
Solidago species are often used in traditional medicine as anti-inflammatory, diuretic, wound-healing and antimicrobial agents. Still, the bioactive compounds and biological activities of some species have not been studied. The present work aimed to investigate the polyphenolic profile and the biological properties of [...] Read more.
Solidago species are often used in traditional medicine as anti-inflammatory, diuretic, wound-healing and antimicrobial agents. Still, the bioactive compounds and biological activities of some species have not been studied. The present work aimed to investigate the polyphenolic profile and the biological properties of Solidago graminifolia L. Salisb., a poorly explored medicinal plant. The hydroalcoholic extracts from aerial parts were evaluated for total phenolic content (TPC), total flavonoid content (TFC) and the polyphenolic compounds were investigated by HPLC-MS. The antioxidant potential in vitro was determined using DPPH and FRAP assays. Antibacterial and antifungal effects were evaluated by dilution assays and MIC, MBC and MFC were calculated. The results showed that Solidago graminifolia aerial parts contain an important amount of total phenolics (192.69 mg GAE/g) and flavonoids (151.41 mg RE/g), with chlorogenic acid and quercitrin as major constituents. The hydroalcoholic extracts showed promising antioxidant and antimicrobial potential, with potent antibacterial activity against Staphylococcus aureus and important antifungal effect against Candida albicans and C. parapsilosis. The obtained results indicated that the aerial parts of Solidago graminifolia could be used as novel resource of phytochemicals in herbal preparations with antioxidant and antimicrobial activities. Full article
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Open AccessArticle
Inhibitory Activity of Plant Essential Oils against E. coli 1-Deoxy-d-xylulose-5-phosphate reductoisomerase
Molecules 2019, 24(14), 2518; https://doi.org/10.3390/molecules24142518 - 10 Jul 2019
Abstract
The rate-limiting enzyme of the 2-methyl-d-erythritol-4-phosphate (MEP) terpenoid biosynthetic pathway, 1-deoxy-d-xylulose-5-phosphate reductoisomerase (DXR), provides the perfect target for screening new antibacterial substances. In this study, we tested the DXR inhibitory effect of 35 plant essential oils (EOs), which have [...] Read more.
The rate-limiting enzyme of the 2-methyl-d-erythritol-4-phosphate (MEP) terpenoid biosynthetic pathway, 1-deoxy-d-xylulose-5-phosphate reductoisomerase (DXR), provides the perfect target for screening new antibacterial substances. In this study, we tested the DXR inhibitory effect of 35 plant essential oils (EOs), which have long been recognized for their antimicrobial properties. The results show that the EOs of Zanbthoxylum bungeanum (ZB), Schizonepetae tenuifoliae (ST), Thymus quinquecostatus (TQ), Origanum vulgare (OV), and Eugenia caryophyllata (EC) displayed weak to medium inhibitory activity against DXR, with IC50 values of 78 μg/mL, 65 μg/mL, 59 μg/mL, 48 μg/mL, and 37 μg/mL, respectively. GC-MS analyses of the above oils and further DXR inhibitory activity tests of their major components revealed that eugenol (EC) and carvacrol (TQ and OV) possess medium inhibition against the protein (68.3% and 55.6%, respectively, at a concentration of 20 μg/mL), whereas thymol (ST, TQ, and OV), carveol (ZB), and linalool (ZB, ST, and OV) only exhibited weak inhibition against DXR, at 20 μg/mL (23%−26%). The results add more details to the antimicrobial mechanisms of plant EOs, which could be very helpful in the direction of the reasonable use of EOs in the food industry and in the control of phytopathogenic microbials. Full article
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Open AccessFeature PaperArticle
A Comparative Study of Black and White Allium sativum L.: Nutritional Composition and Bioactive Properties
Molecules 2019, 24(11), 2194; https://doi.org/10.3390/molecules24112194 - 11 Jun 2019
Abstract
Garlic (Allium sativum L.) has been used worldwide not only for its being a subject of dietary interest, but also for medicinal purposes, in prophylaxis, and for the treatment of diverse pathologies. New processing techniques have been developed and placed on the [...] Read more.
Garlic (Allium sativum L.) has been used worldwide not only for its being a subject of dietary interest, but also for medicinal purposes, in prophylaxis, and for the treatment of diverse pathologies. New processing techniques have been developed and placed on the market in recent years to improve the organoleptic and nutritional value of food products. The present work aimed to study bulbils (cloves) of white (commercial and traditionally cultivated samples with different proveniences) and black (processed samples) garlic. All samples were compared with regard to their nutritional composition as well as their antioxidant and antimicrobial activities. Black garlic had the lowest moisture content but the highest total amount of sugars and energetic value. Black garlic also presented the highest antioxidant and antimicrobial (especially against methicillin-resistant Staphylococcus aureus) activities. Thus, black garlic, obtained by processing techniques, can be considered a promising product with high value that will be able to be exploited by the functional food/nutraceutical industry. Full article
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Open AccessArticle
In Vitro Human Metabolism and Inhibition Potency of Verbascoside for CYP Enzymes
Molecules 2019, 24(11), 2191; https://doi.org/10.3390/molecules24112191 - 11 Jun 2019
Cited by 1
Abstract
Verbascoside is found in many medicinal plant families such as Verbenaceae. Important biological activities have been ascribed to verbascoside. Investigated in this study is the potential of verbascoside as an adjuvant during tuberculosis treatment. The present study reports on the in vitro metabolism [...] Read more.
Verbascoside is found in many medicinal plant families such as Verbenaceae. Important biological activities have been ascribed to verbascoside. Investigated in this study is the potential of verbascoside as an adjuvant during tuberculosis treatment. The present study reports on the in vitro metabolism in human hepatic microsomes and cytosol incubations as well as the presence and quantity of verbascoside within Lippia scaberrima. Additionally, studied are the inhibitory properties on human hepatic CYP enzymes together with antioxidant and cytotoxic properties. The results yielded no metabolites in the hydrolysis or cytochrome P450 (CYP) oxidation incubations. However, five different methylated conjugates of verbascoside could be found in S-adenosylmethionine incubation, three different sulphate conjugates with 3′-phosphoadenosine 5′-phosphosulfate (PAPS) incubation with human liver samples, and very low levels of glucuronide metabolites after incubation with recombinant human uridine 5’-diphospho-glucuronosyltransferase (UGT) 1A7, UGT1A8, and UGT1A10. Additionally, verbascoside showed weak inhibitory potency against CYP1A2 and CYP1B1 with IC50 values of 83 µM and 86 µM, respectively. Potent antioxidant and low cytotoxic potential were observed. Based on these data, verbascoside does not possess any clinically relevant CYP-mediated interaction potential, but it has effective biological activity. Therefore, verbascoside could be considered as a lead compound for further drug development and as an adjuvant during tuberculosis treatment. Full article
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Open AccessCommunication
Anti-Inflammatory Compounds from Atractylodes macrocephala
Molecules 2019, 24(10), 1859; https://doi.org/10.3390/molecules24101859 - 14 May 2019
Cited by 2
Abstract
In relation to anti-inflammatory agents from medicinal plants, we have isolated three compounds from Atractylodes macrocephala; 1, 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-methyl-2, 5-cyclohexadiene-1, 4-dione; 2, 1-acetoxy-tetradeca-6E,12E-diene-8, 10-diyne-3-ol; 3, 1,3-diacetoxy-tetradeca-6E, 12E-diene-8, 10-diyne. Compounds 1 [...] Read more.
In relation to anti-inflammatory agents from medicinal plants, we have isolated three compounds from Atractylodes macrocephala; 1, 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-methyl-2, 5-cyclohexadiene-1, 4-dione; 2, 1-acetoxy-tetradeca-6E,12E-diene-8, 10-diyne-3-ol; 3, 1,3-diacetoxy-tetradeca-6E, 12E-diene-8, 10-diyne. Compounds 13 showed concentration-dependent inhibitory effects on production of nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Western blotting and RT-PCR analyses demonstrated that compounds 13 suppressed the protein and mRNA levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, compounds 13 inhibited transcriptional activity of nuclear factor-κB (NF-κB) and nuclear translocation of NF-κB in LPS-activated RAW 264.7 cells. The most active compound among them, compound 1, could reduce the mRNA levels of pro-inflammatory cytokines (IL-1β, IL-6 and TNF-α) and suppress the phosphorylation of MAPK including p38, JNK, and ERK1/2. Taken together, these results suggest that compounds 13 from A. macrocephala can be therapeutic candidates to treat inflammatory diseases. Full article
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Open AccessReview
A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies
Molecules 2019, 24(9), 1842; https://doi.org/10.3390/molecules24091842 - 13 May 2019
Cited by 1
Abstract
Natural daphnane diterpenoids, mainly distributed in plants of the Thymelaeaceae and Euphorbiaceae families, usually include a 5/7/6-tricyclic ring system with poly-hydroxyl groups located at C-3, C-4, C-5, C-9, C-13, C-14, or C-20, while some special types have a characteristic orthoester motif triaxially connectedat [...] Read more.
Natural daphnane diterpenoids, mainly distributed in plants of the Thymelaeaceae and Euphorbiaceae families, usually include a 5/7/6-tricyclic ring system with poly-hydroxyl groups located at C-3, C-4, C-5, C-9, C-13, C-14, or C-20, while some special types have a characteristic orthoester motif triaxially connectedat C-9, C-13, and C-14. The daphnane-type diterpenoids can be classified into five types: 6-epoxy daphnane diterpenoids, resiniferonoids, genkwanines, 1-alkyldaphnanes and rediocides, based on the oxygen-containing functions at rings B and C, as well as the substitution pattern of ring A. Up to now, nearly 200 daphnane-type diterpenoids have been isolated and elucidated from the Thymelaeaceae and Euphorbiaceae families. In-vitro and in-vivo experiments of these compounds have shown that they possess a wide range of biological activities, including anti-HIV, anti-cancer, anti-leukemic, neurotrophic, pesticidal and cytotoxic effects. A comprehensive account of the structural diversity is given in this review, along with the cytotoxic activities of daphnane-type diterpenoids, up to April 2019. Full article
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Open AccessFeature PaperArticle
Phenolic Profile and Bioactive Properties of Carissa macrocarpa (Eckl.) A.DC.: An In Vitro Comparative Study between Leaves, Stems, and Flowers
Molecules 2019, 24(9), 1696; https://doi.org/10.3390/molecules24091696 - 30 Apr 2019
Cited by 1
Abstract
The present work aimed to characterize leaves, stems, and flowers of Carissa macrocarpa (Eckl.) A.DC., by performing an analysis of the phenolic compounds by HPLC-DAD/ESI-MS, correlating them with bioactive properties, such as antioxidant, anti-inflammatory, cytotoxic, and antimicrobial activities. Thirty polyphenols were identified in [...] Read more.
The present work aimed to characterize leaves, stems, and flowers of Carissa macrocarpa (Eckl.) A.DC., by performing an analysis of the phenolic compounds by HPLC-DAD/ESI-MS, correlating them with bioactive properties, such as antioxidant, anti-inflammatory, cytotoxic, and antimicrobial activities. Thirty polyphenols were identified in the hydroethanolic extract, including phenolic acids, flavan-3-ols, and flavonol glycosides derivatives (which presented the highest number of identified compounds). However, flavan-3-ols showed the highest concentration in stems (mainly owing to the presence of dimers, trimmers, and tetramers of type B (epi)catechin). Leaves were distinguished by their high antioxidant and anti-inflammatory activities, as well as their bactericidal effect against E. coli, while stems presented a higher cytotoxic activity and bactericidal effect against Gram-positive bacteria. Moreover, a high correlation between the studied bioactivities and the presence of phenolic compounds was also verified. The obtained results bring added value to the studied plant species. Full article
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Open AccessArticle
Anticancer Effects of Five Biflavonoids from Ginkgo Biloba L. Male Flowers In Vitro
Molecules 2019, 24(8), 1496; https://doi.org/10.3390/molecules24081496 - 16 Apr 2019
Cited by 4
Abstract
Ginkgo biloba L., an ancient dioecious gymnosperm, is now cultivated worldwide for landscaping and medical purposes. A novel biflavonoid—amentoflavone 7′′-O-β-d-glucopyranoside (1)—and four known biflavonoids were isolated and identified from the male flowers of Ginkgo. The anti-proliferative [...] Read more.
Ginkgo biloba L., an ancient dioecious gymnosperm, is now cultivated worldwide for landscaping and medical purposes. A novel biflavonoid—amentoflavone 7′′-O-β-d-glucopyranoside (1)—and four known biflavonoids were isolated and identified from the male flowers of Ginkgo. The anti-proliferative activities of five biflavonoids were evaluated on different cancer lines. Bilobetin (3) and isoginkgetin (4) exhibited better anti-proliferative activities on different cancer lines. Their effects were found to be cell-specific and in a dose and time dependent manner for the most sensitive HeLa cells. The significant morphological changes validated their anticancer effects in a dose-dependent manner. They were capable of arresting the G2/M phase of the cell cycle, inducing the apoptosis of HeLa cells dose-dependently and activating the proapoptotic protein Bax and the executor caspase-3. Bilobetin (3) could also inhibit the antiapoptotic protein Bcl-2. These might be the mechanism underlying their anti-proliferation. In short, bilobetin (3) and isoginkgetin (4) might be the early lead compounds for new anticancer agents. Full article
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Open AccessArticle
Discovery of Nosiheptide, Griseoviridin, and Etamycin as Potent Anti-Mycobacterial Agents against Mycobacterium avium Complex
Molecules 2019, 24(8), 1495; https://doi.org/10.3390/molecules24081495 - 16 Apr 2019
Abstract
Mycobacterium avium complex (MAC) is a serious disease mainly caused by M. avium and M. intracellulare. Although the incidence of MAC infection is increasing worldwide, only a few agents are clinically used, and their therapeutic effects are limited. Therefore, new anti-MAC agents are [...] Read more.
Mycobacterium avium complex (MAC) is a serious disease mainly caused by M. avium and M. intracellulare. Although the incidence of MAC infection is increasing worldwide, only a few agents are clinically used, and their therapeutic effects are limited. Therefore, new anti-MAC agents are needed. Approximately 6600 microbial samples were screened for new anti-mycobacterial agents that inhibit the growth of both M. avium and M. intracellulare, and two culture broths derived from marine actinomycete strains OPMA1245 and OPMA1730 had strong activity. Nosiheptide (1) was isolated from the culture broth of OPMA1245, and griseoviridin (2) and etamycin (viridogrisein) (3) were isolated from the culture broth of OPMA1730. They had potent anti-mycobacterial activity against M. avium and M. intracellulare with minimum inhibitory concentrations (MICs) between 0.024 and 1.56 μg/mL. In addition, a combination of 2 and 3 markedly enhanced the anti-mycobacterial activity against both M. avium and M. intracellulare. Furthermore, a combination 2 and 3 had a therapeutic effect comparable to that of ethambutol in a silkworm infection assay with M. smegmatis. Full article
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Open AccessCommunication
A Rapid UPLC-MS Method for Quantification of Gomisin D in Rat Plasma and Its Application to a Pharmacokinetic and Bioavailability Study
Molecules 2019, 24(7), 1403; https://doi.org/10.3390/molecules24071403 - 10 Apr 2019
Cited by 1
Abstract
Gomisin D, a lignan compound isolated from Fructus Schisandra, is a potential antidiabetic and anti-Alzheimer’s agent. Recently, gomisin D was used as a quality marker of some traditional Chinese medicine (TCM) formulas. In this study, a rapid ultra-performance liquid chromatography/tandem mass spectrometry [...] Read more.
Gomisin D, a lignan compound isolated from Fructus Schisandra, is a potential antidiabetic and anti-Alzheimer’s agent. Recently, gomisin D was used as a quality marker of some traditional Chinese medicine (TCM) formulas. In this study, a rapid ultra-performance liquid chromatography/tandem mass spectrometry method (UPLC-MS/MS) was developed and validated to quantify gomisin D in rat plasma for a pharmacokinetic and bioavailability study. Acetonitrile was used to precipitate plasma proteins. Separations were performed on a BEH C18 column with a gradient mobile phase comprising of acetonitrile and water (0.1% formic acid). An electrospray ionization source was applied and operated in the positive ion mode. The multiple reaction monitoring mode (MRM) was utilized to quantify gomisin D and nomilin (internal standard, IS) using the transitions of m/z 531.2 → 383.1 and m/z 515.3 → 161.0, respectively. The calibration curve was linear over the working range from 1 to 4000 ng/mL (R2 = 0.993). The intra- and interday precision ranged from 1.9% to 12.9%. The extraction recovery of gomisin D was in the range of 79.2–86.3%. The validated UPLC-MS/MS method was then used to obtain the pharmacokinetic characteristics of gomisin D after intravenous (5 mg/kg) and intragastric (50 mg/kg) administration to rats. The bioavailability of gomisin D was 107.6%, indicating that this compound may become a promising intragastrical medication. Our results provided useful information for further preclinical studies on gomisin D. Full article
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Open AccessReview
Alcyonium Octocorals: Potential Source of Diverse Bioactive Terpenoids
Molecules 2019, 24(7), 1370; https://doi.org/10.3390/molecules24071370 - 08 Apr 2019
Cited by 1
Abstract
Alcyonium corals are benthic animals, which live in different climatic areas, including temperate, Antarctic and sub-Antarctic waters. They were found to produce different chemical substances with molecular diversity and unique architectures. These metabolites embrace several terpenoidal classes with different functionalities. This wide array [...] Read more.
Alcyonium corals are benthic animals, which live in different climatic areas, including temperate, Antarctic and sub-Antarctic waters. They were found to produce different chemical substances with molecular diversity and unique architectures. These metabolites embrace several terpenoidal classes with different functionalities. This wide array of structures supports the productivity of genus Alcyonium. Yet, majority of the reported compounds are still biologically unscreened and require substantial efforts to explore their importance. This review is an entryway to push forward the bio-investigation of this genus. It covers the era from the beginning of reporting metabolites from Alcyonium up to March 2019. Ninety-two metabolites are presented; forty-two sesquiterpenes, twenty-five diterpenes and twenty-five steroids have been reported from sixteen species. Full article
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Open AccessArticle
The Impact of Processing Parameters on the Content of Phenolic Compounds in New Gluten-Free Precooked Buckwheat Pasta
Molecules 2019, 24(7), 1262; https://doi.org/10.3390/molecules24071262 - 01 Apr 2019
Cited by 2
Abstract
Buckwheat is a generous source of phenolic compounds, vitamins and essential amino acids. This paper discusses the procedure of obtaining innovative gluten-free, precooked pastas from roasted buckwheat grains flour, a fertile source of natural antioxidants, among them, phenolic acids. The authors also determined [...] Read more.
Buckwheat is a generous source of phenolic compounds, vitamins and essential amino acids. This paper discusses the procedure of obtaining innovative gluten-free, precooked pastas from roasted buckwheat grains flour, a fertile source of natural antioxidants, among them, phenolic acids. The authors also determined the effect of the extruder screw speed and the level of moisture content in the raw material on the quantity of free phenolic acids. The qualitative and quantitative analysis of phenolic acids in pasta was carried out using high-performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). The chromatographic method was validated. For extracts with the highest total content of free phenolic acids and unprocessed flour from roasted buckwheat grain, the TLC-DPPH test was also performed to determine the antioxidant properties of the tested pasta. The level of moisture in the raw material had an impact on the content of phenolic acids. All pastas made from buckwheat flour moistened up to 32% exhibited a higher total content of free phenolic acids than other mixes moistened to 30 and 34% of water. Full article
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Open AccessArticle
Four Novel Dammarane-Type Triterpenoids from Pearl Knots of Panax ginseng Meyer cv. Silvatica
Molecules 2019, 24(6), 1159; https://doi.org/10.3390/molecules24061159 - 23 Mar 2019
Cited by 1
Abstract
Panax ginseng Meyer cv. Silvatica (PGS), which is also known as “Lin-Xia-Shan-Shen” or “Zi-Hai” in China, is grown in forests and mountains by broadcasting the seeds of ginseng and is harvested at the cultivation age of 15–20 years. In this study, four new [...] Read more.
Panax ginseng Meyer cv. Silvatica (PGS), which is also known as “Lin-Xia-Shan-Shen” or “Zi-Hai” in China, is grown in forests and mountains by broadcasting the seeds of ginseng and is harvested at the cultivation age of 15–20 years. In this study, four new dammarane-type triterpenoids, ginsengenin-S1 (1), ginsengenin-S2 (2), ginsenoside-S3 (3), ginsenoside-S4 (4), along with one known compound were isolated from pearl knots of PGS. Ginsengenin-S2 significantly alleviated oxidative damage when A549 cells were exposed to cigarette smoke (CS) extract. In addition, ginsengenin-S2 could inhibit the CS-induced inflammatory reaction in A549 cells. Protective effects of ginsengenin-S2 against CS-mediated oxidative stress and the inflammatory response in A549 cells may involve the Nrf2 and HDAC2 pathways. Full article
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Open AccessFeature PaperArticle
Cytinus hypocistis (L.) L. subsp. macranthus Wettst.: Nutritional Characterization
Molecules 2019, 24(6), 1111; https://doi.org/10.3390/molecules24061111 - 20 Mar 2019
Cited by 1
Abstract
The habit of eating wild plants in Europe is often associated with times of famine; an example of such is the nectar of Cytinus hypocistis (L.) L., a parasitic plant. To the authors’ best knowledge, there are no studies on its nutritional and [...] Read more.
The habit of eating wild plants in Europe is often associated with times of famine; an example of such is the nectar of Cytinus hypocistis (L.) L., a parasitic plant. To the authors’ best knowledge, there are no studies on its nutritional and chemical composition; thus, the whole C. hypocistis (L.) L. subsp. macranthus Wettst. plant (CH) and its nectar (NCH) were nutritionally and chemically characterized. The proximate composition of CH and NCH were very similar in terms of energy, ash, and carbohydrate content. Protein and fat were approximately 2-fold higher in NCH, and crude fiber was 4.6-fold higher in CH compared to NCH. Fructose, glucose, sucrose, and trehalose were the free sugars present in both samples. Oxalic, malic, and citric acids were the identified organic acids in both samples, with citric acid as the most abundant molecule. For both samples, polyunsaturated and saturated fatty acids (PUFA and SFA, respectively) predominate over monounsaturated fatty acids (MUFA) due to the significant contribution of linoleic and palmitic acids, respectively. However, unsaturated fatty acids (UFA) prevail over SFA in CH and NCH. Therefore, CH proved to be an excellent source of nutritional compounds, which supports its use during past periods of scarcity. Full article
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Open AccessArticle
Optimization of Ultrasound-Assisted Extraction of Phenolic Compounds from Annona muricata By-Products and Pulp
Molecules 2019, 24(5), 904; https://doi.org/10.3390/molecules24050904 - 05 Mar 2019
Cited by 3
Abstract
Ultrasound-assisted extraction (UAE) is widely used; however, the efficiency of extraction depends on the raw materials. Therefore, optimization of UAE must be investigated for each type of plant material. By-products from soursop fruit have not been studied as a source of bioactive compounds. [...] Read more.
Ultrasound-assisted extraction (UAE) is widely used; however, the efficiency of extraction depends on the raw materials. Therefore, optimization of UAE must be investigated for each type of plant material. By-products from soursop fruit have not been studied as a source of bioactive compounds. In this work, the optimization of UAE conditions (extraction time (5, 10, and 15 min), pulse cycle (0.4, 0.7, and 1 s), and sonication amplitude (40%, 70%, and 100%)) for the extraction of phenolic compounds (soluble, hydrolyzable, condensed tannins, and total polyphenols) from soursop by-products (seed, peel, and columella) and pulp was evaluated using response surface methodology. The optimal conditions for UAE to obtain the highest total polyphenol content from by-products and pulp was dependent on the raw material. Peel resulted in the highest content of total polyphenols (187.32 mg/g dry matter [DM]) followed by columella (164.14 mg/g DM), seed (36.15 mg/g DM), and pulp (33.24 mg/g DM). The yield of polyphenolic content from peel and columella obtained with UAE was higher (32–37%) than conventional extraction for 2 h under stirring (14–16%). The contents of gallic acid (0.36–15.86 µg/g DM), coumaric acid (0.07–1.37 µg/g DM), and chlorogenic acid (9.18–32.67 µg/g DM) in the different parts of the fruit were higher in the extracts obtained by UAE compared with a conventional extraction method (0.08–0.61, 0.05–0.08, 3.15–13.08 µg/g DM, respectively), although it was dependent on the raw materials. Soursop by-products can be functionally important if they are used to extract bioactive compounds by UAE; a technology with high potential for commercial extraction on a large scale. Full article
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Open AccessArticle
Echinacoside Isolated from Cistanche tubulosa Putatively Stimulates Growth Hormone Secretion via Activation of the Ghrelin Receptor
Molecules 2019, 24(4), 720; https://doi.org/10.3390/molecules24040720 - 17 Feb 2019
Cited by 4
Abstract
Cistanche species, the ginseng of the desert, has been recorded to possess many biological activities in traditional Chinese pharmacopoeia and has been used as an anti-aging medicine. Three phenylethanoid glycosides—echinacoside, tubuloside A, and acteoside—were detected in the water extract of Cistanche tubulosa (Schenk) [...] Read more.
Cistanche species, the ginseng of the desert, has been recorded to possess many biological activities in traditional Chinese pharmacopoeia and has been used as an anti-aging medicine. Three phenylethanoid glycosides—echinacoside, tubuloside A, and acteoside—were detected in the water extract of Cistanche tubulosa (Schenk) R. Wight and the major constituent, echinacoside, was further purified. Echinacoside of a concentration higher than 10−6 M displayed significant activity to stimulate growth hormone secretion of rat pituitary cells. Similar to growth hormone-releasing hormone-6, a synthetic analog of ghrelin, the stimulation of growth hormone secretion by echinacoside was inhibited by [D-Arg1, D-Phe5, D-Trp7,9, Leu11]-substance P, an inverse agonist of the ghrelin receptor. Molecular modeling showed that all the three phenylethanoid glycosides adequately interacted with the binding pocket of the ghrelin receptor, and echinacoside displayed a slightly better interaction with the receptor than tubuloside A and acteoside. The results suggest that phenylethanoid glycosides, particularly echinacoside, are active constituents putatively responsible for the anti-aging effects of C. tubulosa and may be considered to develop as non-peptidyl analogues of ghrelin. Full article
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Open AccessReview
Bioactivity Profile of the Diterpene Isosteviol and its Derivatives
Molecules 2019, 24(4), 678; https://doi.org/10.3390/molecules24040678 - 14 Feb 2019
Cited by 6
Abstract
Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent [...] Read more.
Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advances. Full article
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Open AccessArticle
Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma
Molecules 2019, 24(3), 554; https://doi.org/10.3390/molecules24030554 - 03 Feb 2019
Abstract
A new cytotoxic cyclononapeptide, sclerin, cyclo(–Dab1–Ser2–Tyr3–Gly4–Thr5–Val6–Ala7– Ile8–Pro9–) (1), was isolated from the methanol extract of the seeds of Annona scleroderma, together with [...] Read more.
A new cytotoxic cyclononapeptide, sclerin, cyclo(–Dab1–Ser2–Tyr3–Gly4–Thr5–Val6–Ala7– Ile8–Pro9–) (1), was isolated from the methanol extract of the seeds of Annona scleroderma, together with the known metabolite, cyclosenegalin A, cyclo(–Pro1–Gly2–Leu3–Ser4–Ala5–Val6–Thr7–) (2). The planar structures for the two compounds were established by comprehensive analysis of NMR and ESI-HRMS data, and the absolute stereochemistry was stablished by Marfey’s method. Compound 1 showed moderate cytotoxic activity against the human prostate carcinoma cell line DU-145 at µM concentration. Full article
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Open AccessCommunication
Discovery of Three New Phytotoxins from the Fungus Aspergillus nidulans by Pathway Inactivation
Molecules 2019, 24(3), 515; https://doi.org/10.3390/molecules24030515 - 31 Jan 2019
Abstract
Fungi are a source of novel phytotoxic compounds to be explored in the search for effective and environmentally safe herbicides. The genetic inactivation of the biosynthetic pathway of the new phytotoxin cichorine has led to the isolation of three novel phytotoxins from the [...] Read more.
Fungi are a source of novel phytotoxic compounds to be explored in the search for effective and environmentally safe herbicides. The genetic inactivation of the biosynthetic pathway of the new phytotoxin cichorine has led to the isolation of three novel phytotoxins from the fungus Aspergillus nidulans: 8-methoxycichorine (4), 8-epi-methoxycichorine (5), and N-(4’-carboxybutyl) cichorine (6). The structure of the new compounds was clearly determined by a combination of nuclear magnetic resonance (NMR) analysis and high-resolution electrospray ionization (HRESIMS). The phytotoxic bioassay was studied on leaves from Zea mays and Medicago polymorpha L. at the concentration of 5 × 10−3 M by using a moist chamber technique. Novel phytotoxins 8-methoxycichorine (4), 8-epi-methoxycichorine (5), and N-(4’-carboxybutyl) cichorine (6) exhibited a better phytotoxic effect than cichorine. Full article
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Open AccessArticle
Rare Acetogenins with Anti-Inflammatory Effect from the Red Alga Laurencia obtusa
Molecules 2019, 24(3), 476; https://doi.org/10.3390/molecules24030476 - 29 Jan 2019
Abstract
Three new rare C12 acetogenins (enyne derivatives 13) were isolated from the organic extract obtained from the red alga Laurencia obtusa, collected from the Red Sea. The chemical structures of the isolated compounds were established by spectroscopical data [...] Read more.
Three new rare C12 acetogenins (enyne derivatives 13) were isolated from the organic extract obtained from the red alga Laurencia obtusa, collected from the Red Sea. The chemical structures of the isolated compounds were established by spectroscopical data analyses. Potent anti-inflammatory effect of the isolated metabolites was evidenced by inhibition of the release of inflammatory mediators (e.g., TNF-α, IL-1β and IL-6) by employing Human Peripheral Blood Mononuclear Cells (PBMC). Full article
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Open AccessReview
A Review on the Phytochemistry, Medicinal Properties and Pharmacological Activities of 15 Selected Myanmar Medicinal Plants
Molecules 2019, 24(2), 293; https://doi.org/10.3390/molecules24020293 - 15 Jan 2019
Cited by 7
Abstract
Medicinal plants are a reservoir of biologically active compounds with therapeutic properties that over time have been reported and used by diverse groups of people for treatment of various diseases. This review covers 15 selected medicinal plants distributed in Myanmar, including Dalbergia cultrata [...] Read more.
Medicinal plants are a reservoir of biologically active compounds with therapeutic properties that over time have been reported and used by diverse groups of people for treatment of various diseases. This review covers 15 selected medicinal plants distributed in Myanmar, including Dalbergia cultrata, Eriosema chinense, Erythrina suberosa, Millettia pendula, Sesbania grandiflora, Tadehagi triquetrum, Andrographis echioides, Barleria cristata, Justicia gendarussa, Premna integrifolia, Vitex trifolia, Acacia pennata, Cassia auriculata, Croton oblongifolius and Glycomis pentaphylla. Investigation of the phytochemical constituents, biological and pharmacological activities of the selected medicinal plants is reported. This study aims at providing a collection of publications on the species of selected medicinal plants in Myanmar along with a critical review of the literature data. As a country, Myanmar appears to be a source of traditional drugs that have not yet been scientifically investigated. This review will be support for further investigations on the pharmacological activity of medicinal plant species in Myanmar. Full article
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Open AccessFeature PaperArticle
Erubescensoic Acid, a New Polyketide and a Xanthonopyrone SPF-3059-26 from the Culture of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA 0220 and Antibacterial Activity Evaluation of Some of Its Constituents
Molecules 2019, 24(1), 208; https://doi.org/10.3390/molecules24010208 - 08 Jan 2019
Cited by 1
Abstract
A new polyketide erubescensoic acid (1), and the previously reported xanthonopyrone, SPF-3059-26 (2), were isolated from the uninvestigated fractions of the ethyl acetate crude extract of the marine sponge-associated fungus Penicillium erubescens KUFA0220. The structures of the new compound, [...] Read more.
A new polyketide erubescensoic acid (1), and the previously reported xanthonopyrone, SPF-3059-26 (2), were isolated from the uninvestigated fractions of the ethyl acetate crude extract of the marine sponge-associated fungus Penicillium erubescens KUFA0220. The structures of the new compound, erubescensoic acid (1), and the previously reported SPF-3059-26 (2), were elucidated by extensive analysis of 1D and 2D-NMR spectra as well as HRMS. The absolute configuration of the stereogenic carbon of erubescensoic acid (1) was determined by X-ray analysis. Erubescensoic acid (1) and SPF-3059-26 (2), together with erubescenschromone B (3), penialidin D (4), and 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromen-5-carboxylic acid (5), recently isolated from this fungus, were assayed for their antibacterial activity against gram-positive and gram-negative reference strains and the multidrug-resistant (MDR) strains from the environment. The capacity of these compounds to interfere with the bacterial biofilm formation and their potential synergism with clinically relevant antibiotics for the MDR strains were also investigated. Full article
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Open AccessArticle
Chemical Eustress Elicits Tailored Responses and Enhances the Functional Quality of Novel Food Perilla frutescens
Molecules 2019, 24(1), 185; https://doi.org/10.3390/molecules24010185 - 06 Jan 2019
Cited by 9
Abstract
Consumer demand for fresh and functional horticultural products is on the rise. Perilla frutescens, L. Britt (Lamiaceae) is a potential specialty/niche crop for consumption and therapeutic uses with high contents of phenolic and volatile compounds. Plant growth, mineral composition, polyphenol [...] Read more.
Consumer demand for fresh and functional horticultural products is on the rise. Perilla frutescens, L. Britt (Lamiaceae) is a potential specialty/niche crop for consumption and therapeutic uses with high contents of phenolic and volatile compounds. Plant growth, mineral composition, polyphenol profile and aroma volatile components of two perilla genotypes in response to salinity (non-salt control, 10, 20 or 30 mM NaCl) applied as chemical eustressor were assessed. Salinity suppressed growth and yield of both genotypes, although the red-pigmented genotype was less sensitive than the green-pigmented one. Mild (10 mM NaCl) and moderate (20 and 30 mM NaCl) salinity suppressed foliar potassium, magnesium, nitrate and chlorophyll a concentrations of both genotypes and increased the levels of rosmarinic acid, total polyphenols and target aroma volatile components. Green perilla showed higher yield and biomass production and higher content of protein, dry matter, calcium, magnesium, perilla ketone and cis-jasmone, whereas red perilla exhibited higher content of potassium, chlorophyll a, rosmarinic acid, total polyphenols, perilla aldehyde and benzaldehyde. Our findings support that chemical eustressors such as mild to moderate salinity offer valuable means to manipulate phytochemical and aroma profiles. Full article
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2018

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Open AccessArticle
Identification of Antioxidant Peptides in Enzymatic Hydrolysates of Carp (Cyprinus Carpio) Skin Gelatin
Molecules 2019, 24(1), 97; https://doi.org/10.3390/molecules24010097 - 28 Dec 2018
Cited by 7
Abstract
The protein by-products from carp (Cyprinus carpio) are normally discarded as industrial waste during fish processing. The objective of this study was to identify and characterise the peptides with a potential antioxidant activity that are released from carp skin proteins during [...] Read more.
The protein by-products from carp (Cyprinus carpio) are normally discarded as industrial waste during fish processing. The objective of this study was to identify and characterise the peptides with a potential antioxidant activity that are released from carp skin proteins during hydrolysis by the Protamex enzyme mixture. This study shows that a hydrolysate of carp skin gelatin and its reversed-phase chromatography fractions have strong in vitro antioxidant properties. Among these fractions, the alanine-tyrosine (Ala-Tyr) dipeptide was identified as the major compound with high antioxidant potential. The peptide has good stability during in vitro enzymatic digestion assay and can inhibit the angiotensin-converting enzyme (ACE). In conclusion, our study proves that both the unfractionated hydrolysate of carp skin gelatin and the above-mentioned Ala-Tyr dipeptide represents attractive novel compounds for the formulation of antioxidant foods. Full article
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Open AccessArticle
Isolation, Chemical Profile and Antimalarial Activities of Bioactive Compounds from Rauvolfia caffra Sond
Molecules 2019, 24(1), 39; https://doi.org/10.3390/molecules24010039 - 21 Dec 2018
Cited by 2
Abstract
In this study, the chemical profile of a crude methanol extract of Rauvolfia caffra Sond was determined by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). Column chromatography and preparative thin layer chromatography were used to isolate three indole alkaloids (raucaffricine, N-methylsarpagine and spegatrine) and [...] Read more.
In this study, the chemical profile of a crude methanol extract of Rauvolfia caffra Sond was determined by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). Column chromatography and preparative thin layer chromatography were used to isolate three indole alkaloids (raucaffricine, N-methylsarpagine and spegatrine) and one triterpenoid (lupeol). The antiplasmodial activity was determined using the parasite lactate dehydrogenase (pLDH) assay. The UPLC-MS profile of the crude extract reveals that the major constituents of R. caffra are raucaffricine (m/z 513.2) and spegatrine (m/z 352.2). Fraction 3 displayed the highest antiplasmodial activity with an IC50 of 6.533 μg/mL. However, raucaffricine, isolated from the active fraction did not display any activity. The study identifies the major constituents of R. caffra and also demonstrates that the major constituents do not contribute to the antiplasmodial activity of R. caffra. Full article
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Open AccessReview
The Potential Use of Plant Natural Products and Plant Extracts with Antioxidant Properties for the Prevention/Treatment of Neurodegenerative Diseases: In Vitro, In Vivo and Clinical Trials
Molecules 2018, 23(12), 3283; https://doi.org/10.3390/molecules23123283 - 11 Dec 2018
Cited by 28
Abstract
Neurodegenerative disorders, including Alzheimer’s disease, Parkinson’s disease and Huntington’s disease, present a major health issue and financial burden for health care systems around the world. The impact of these diseases will further increase over the next decades due to increasing life expectancies. No [...] Read more.
Neurodegenerative disorders, including Alzheimer’s disease, Parkinson’s disease and Huntington’s disease, present a major health issue and financial burden for health care systems around the world. The impact of these diseases will further increase over the next decades due to increasing life expectancies. No cure is currently available for the treatment of these conditions; only drugs, which merely alleviate the symptoms. Oxidative stress has long been associated with neurodegeneration, whether as a cause or as part of the downstream results caused by other factors. Thus, the use of antioxidants to counter cellular oxidative stress within the nervous system has been suggested as a potential treatment option for neurological disorders. Over the last decade, significant research has focused on the potential use of natural antioxidants to target oxidative stress. However, clinical trial results have lacked success for the treatment of patients with neurological disorders. The knowledge that natural extracts show other positive molecular activities in addition to antioxidant activity, however, has led to further research of natural extracts for their potential use as prevention or treatment/management of neurodegenerative diseases. This review will cover several in vitro and in vivo research studies, as well as clinical trials, and highlight the potential of natural antioxidants. Full article
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Open AccessArticle
Simultaneous Quantitation of Isoprenoid Pyrophosphates in Plasma and Cancer Cells Using LC-MS/MS
Molecules 2018, 23(12), 3275; https://doi.org/10.3390/molecules23123275 - 11 Dec 2018
Cited by 3
Abstract
Isoprenoids (IsoP) are an important class of molecules involved in many different cellular processes including cholesterol synthesis. We have developed a sensitive and specific LC-MS/MS method for the quantitation of three key IsoPs in bio-matrices, geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl [...] Read more.
Isoprenoids (IsoP) are an important class of molecules involved in many different cellular processes including cholesterol synthesis. We have developed a sensitive and specific LC-MS/MS method for the quantitation of three key IsoPs in bio-matrices, geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP). LC-MS/MS analysis was performed using a Nexera UPLC System connected to a LCMS-8060 (Shimadzu Scientific Instruments, Columbia, MD) with a dual ion source. The electrospray ionization source was operated in the negative MRM mode. The chromatographic separation and detection of analytes was achieved on a reversed phase ACCQ-TAG Ultra C18 (1.7 µm, 100 mm × 2.1 mm I.D.) column. The mobile phase consisted of (1) a 10 mM ammonium carbonate with 0.1% ammonium hydroxide in water, and (2) a 0.1% ammonium hydroxide in acetonitrile/methanol (75/25). The flow rate was set to 0.25 mL/min in a gradient condition. The limit of quantification was 0.04 ng/mL for all analytes with a correlation coefficient (r2) of 0.998 or better and a total run time of 12 min. The inter- and intra-day accuracy (85–115%) precision (<15%), and recovery (40–90%) values met the acceptance criteria. The validated method was successfully applied to quantitate basal concentrations of GPP, FPP and GGPP in human plasma and in cultured cancer cell lines. Our LC-MS/MS method may be used for IsoP quantification in different bio-fluids and to further investigate the role of these compounds in various physiological processes. Full article
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Open AccessArticle
Chemical Characterization and Hypoglycaemic Activities In Vitro of Two Polysaccharides from Inonotus obliquus by Submerged Culture
Molecules 2018, 23(12), 3261; https://doi.org/10.3390/molecules23123261 - 10 Dec 2018
Cited by 5
Abstract
Polysaccharides from the fungus Inonotus obliquus have been found to be biologically active. In this study, we carried out a preliminary characterisation and assessment of the hypoglycaemic activities of the polysaccharides (IOEP) from Inonotus obliquus obtained by liquid fermentation. Two polysaccharides, IOEP1 and [...] Read more.
Polysaccharides from the fungus Inonotus obliquus have been found to be biologically active. In this study, we carried out a preliminary characterisation and assessment of the hypoglycaemic activities of the polysaccharides (IOEP) from Inonotus obliquus obtained by liquid fermentation. Two polysaccharides, IOEP1 and IOEP2, were isolated from IOEP. IOEP1, with a molecular weight of 20 KDa, was mainly composed of galatose and mannose, while IOEP2, with a molecular weight of 200 KDa, was mainly composed of arabinose. Fourier-transform infrared analysis showed that both IOEP1 and IOEP2 were pyran-type polysaccharides. 1H-NMR spectra showed that the glycosidic bonds of IOEP1 and IOEP2 were both α-type and β-type. In addition, IOEP1 and IOEP2 strongly increased the glucose consumption of HepG2 cells and insulin-resistant HepG2 cells in vitro. These findings provide a theoretical basis that IOEP1 and IOEP2 might be suitable as anti-diabetes agents in functional foods and natural drugs. Full article
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Open AccessArticle
Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species
Molecules 2018, 23(12), 3199; https://doi.org/10.3390/molecules23123199 - 04 Dec 2018
Cited by 2
Abstract
A phytochemical investigation of the roots of Aspilia pluriseta led to the isolation of ent-kaurane-type diterpenoids and additional phytochemicals (123). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric [...] Read more.
A phytochemical investigation of the roots of Aspilia pluriseta led to the isolation of ent-kaurane-type diterpenoids and additional phytochemicals (123). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analyses. The absolute configurations of seven of the ent-kaurane-type diterpenoids (36, 6b, 7 and 8) were determined by single crystal X-ray diffraction studies. Eleven of the compounds were also isolated from the roots and the aerial parts of Aspilia mossambicensis. The literature NMR assignments for compounds 1 and 5 were revised. In a cytotoxicity assay, 12α-methoxy-ent-kaur-9(11),16-dien-19-oic acid (1) (IC50 = 27.3 ± 1.9 µM) and 9β-hydroxy-15α-angeloyloxy-ent-kaur-16-en-19-oic acid (3) (IC50 = 24.7 ± 2.8 µM) were the most cytotoxic against the hepatocellular carcinoma (Hep-G2) cell line, while 15α-angeloyloxy-16β,17-epoxy-ent-kauran-19-oic acid (5) (IC50 = 30.7 ± 1.7 µM) was the most cytotoxic against adenocarcinomic human alveolar basal epithelial (A549) cells. Full article
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Open AccessArticle
Anti-Inflammatory, Antioxidant, and Hypolipidemic Effects of Mixed Nuts in Atherogenic Diet-Fed Rats
Molecules 2018, 23(12), 3126; https://doi.org/10.3390/molecules23123126 - 29 Nov 2018
Cited by 4
Abstract
Nut consumption is associated with reduced risk of cardiovascular disease (CVD). Because most studies have administered single nut varieties, it is unknown whether mixed nuts will also reduce CVD risk. The objective of this study was to compare the effects of mixed nut [...] Read more.
Nut consumption is associated with reduced risk of cardiovascular disease (CVD). Because most studies have administered single nut varieties, it is unknown whether mixed nuts will also reduce CVD risk. The objective of this study was to compare the effects of mixed nut and pistachio consumption on lipid profiles, glucose, inflammation, oxidative stress, and antioxidant capacity in rats fed an atherogenic diet. Thirty male Sprague-Dawley rats (21 days old) were assigned into three groups (n = 10) based on initial body weight and fed either an isocaloric control diet (no nuts), 8.1% pistachio diet (single nut), or 7.5% mixed nut diet (almonds, brazil nuts, cashews, macadamia nuts, peanuts, pecans, pistachios, and walnuts) for 8 weeks. Both pistachios and mixed nuts significantly decreased triglycerides, total cholesterol, and LDL-cholesterol (p < 0.05) compared with controls. Both nut groups exhibited reductions in C-reactive protein (p = 0.045) and oxidative stress (p = 0.004). The mixed nut group had greater superoxide dismutase (p = 0.004) and catalase (p = 0.044) and lower aspartate aminotransferase (p = 0.048) activities. Gene expression for Fas, Hmgcr, and Cox2 was downregulated for both nut groups compared to controls (p < 0.05). In conclusion, mixed nuts and individual nut varieties have comparable effects on CVD risk factors in rats. Full article
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Open AccessArticle
Characterization and Prebiotic Potential of Longan Juice Obtained by Enzymatic Conversion of Constituent Sucrose into Fructo-Oligosaccharides
Molecules 2018, 23(10), 2596; https://doi.org/10.3390/molecules23102596 - 10 Oct 2018
Cited by 1
Abstract
The prebiotic potential of longan juice obtained by a commercial Viscozyme L for conversion of constituent sucrose to fructo-oligosaccharide was investigated. The physicochemical properties and carbohydrate composition of the longan juice was evaluated before and after enzymatic treatment. The stimulation effects of the [...] Read more.
The prebiotic potential of longan juice obtained by a commercial Viscozyme L for conversion of constituent sucrose to fructo-oligosaccharide was investigated. The physicochemical properties and carbohydrate composition of the longan juice was evaluated before and after enzymatic treatment. The stimulation effects of the treated longan juice on probiotic bacteria growth were also studied in vitro. The results showed that total soluble solids, yield and clarity of longan juice were all significantly improved after enzyme treatment. The water-soluble polysaccharide content, including pectin, was significantly increased. Compared with the natural longan pulp, the enzyme treated juice showed a significant decrease in sucrose content. Substantial fructo-oligosaccharides including 1-kestose and nystose were synthesized after enzyme treatment. The molecular weight distribution and the monosaccharide composition of the water-soluble polysaccharide were significantly changed by enzyme treatment. The treated longan juice and its ethanol-soluble sugar fraction promoted the growth of Streptococus thermophiles, Lactobacillus acidophilus and Lactobacillus delbrueckii, showing a good potential of the treated longan juice for producing functional foods and nutraceuticals. Full article
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Open AccessArticle
Identification of Anti-Melanogenesis Constituents from Morus alba L. Leaves
Molecules 2018, 23(10), 2559; https://doi.org/10.3390/molecules23102559 - 08 Oct 2018
Cited by 7
Abstract
The individual parts of Morus alba L. including root bark, branches, leaves, and fruits are used as a cosmetic ingredient in many Asian countries. This study identified several anti-melanogenesis constituents in a 70% ethanol extract of M. alba leaves. The ethyl acetate fraction [...] Read more.
The individual parts of Morus alba L. including root bark, branches, leaves, and fruits are used as a cosmetic ingredient in many Asian countries. This study identified several anti-melanogenesis constituents in a 70% ethanol extract of M. alba leaves. The ethyl acetate fraction of the initial ethanol extract decreased the activity of tyrosinase, a key enzyme in the synthetic pathway of melanin. Twelve compounds were isolated from this fraction and their structures were identified based on spectroscopic spectra. Then, the authors investigated the anti-melanogenesis effects of the isolated compounds in B16-F10 mouse melanoma cells. Compounds 3 and 8 significantly inhibited not only melanin production but also intracellular tyrosinase activity in alpha-melanocyte-stimulating-hormone (α-MSH)-induced B16-F10 cells in a dose-dependent manner. These same compounds also inhibited melanogenesis-related protein expression such as microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1). Compound 3 modulated the cAMP-responsive element-binding protein (CREB) and p38 signaling pathways in α-MSH-activated B16-F10 melanoma cells, which resulted in the anti-melanogenesis effects. These results suggest that compound 3, isolated from M. alba leaves, could be used to inhibit melanin production via the regulation of melanogenesis-related protein expression. Full article
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Open AccessArticle
Similarity of Data from Bee Bread with the Same Taxa Collected in India and Romania
Molecules 2018, 23(10), 2491; https://doi.org/10.3390/molecules23102491 - 28 Sep 2018
Cited by 8
Abstract
Bee Bread samples from Romania and India were analysed by microscopy and High Performance Liquid Chromatography with Diode Array Detection (HPLC/DAD) and compared with pollen from the correspondent taxa. The quantification of sugars, fructose/glucose ratio, total phenolics and flavonoids was also carried out. [...] Read more.
Bee Bread samples from Romania and India were analysed by microscopy and High Performance Liquid Chromatography with Diode Array Detection (HPLC/DAD) and compared with pollen from the correspondent taxa. The quantification of sugars, fructose/glucose ratio, total phenolics and flavonoids was also carried out. From the results was possible to identify Brassica and Eucalyptus samples that present similar HPLC/DAD profiles with the respective ultraviolet (UV) identification of the main compounds as Kaempferol-3-O-glycosides and Hydrocinnamic acid derivatives. The Fructose/Glucose (F/G) ratio and the total amounts of phenolics and flavonoids was in line with the prevalence of the specie identified. These coincident fingerprints gave the identification of the samples, as was previously proposed for bee pollens. This paper relates for the first time the achievement on the taxon carried out previously only for bee pollens. It was reported for the first time that this phenolic profile remains unchanged in the case of floral pollen (hand collected), bee pollen and bee bread. Despite the biochemical transformation that occurs during the fermentation of bee bread, it seems that these phenolic compounds are not affected and remain unchanged. Also, variables such as soil and climate do not seem to influence these compounds for the kind of samples under study. Full article
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Open AccessArticle
Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies
Molecules 2018, 23(10), 2479; https://doi.org/10.3390/molecules23102479 - 27 Sep 2018
Cited by 12
Abstract
Okinawa propolis (OP) and its major ingredients were reported to have anti-cancer effects and lifespan-extending effects on Caenorhabditis elegans through inactivation of the oncogenic kinase, p21-activated kinase 1 (PAK1). Herein, five prenylated flavonoids from OP, nymphaeol-A (NA), nymphaeol-B (NB), nymphaeol-C (NC), isonymphaeol-B (INB), [...] Read more.
Okinawa propolis (OP) and its major ingredients were reported to have anti-cancer effects and lifespan-extending effects on Caenorhabditis elegans through inactivation of the oncogenic kinase, p21-activated kinase 1 (PAK1). Herein, five prenylated flavonoids from OP, nymphaeol-A (NA), nymphaeol-B (NB), nymphaeol-C (NC), isonymphaeol-B (INB), and 3′-geranyl-naringenin (GN), were evaluated for their anti-inflammatory, anti-diabetic, and anti-Alzheimer’s effects using in vitro techniques. They showed significant anti-inflammatory effects through inhibition of albumin denaturation (half maximal inhibitory concentration (IC50) values of 0.26–1.02 µM), nitrite accumulation (IC50 values of 2.4–7.0 µM), and cyclooxygenase-2 (COX-2) activity (IC50 values of 11.74–24.03 µM). They also strongly suppressed in vitro α-glucosidase enzyme activity with IC50 values of 3.77–5.66 µM. However, only INB and NA inhibited acetylcholinesterase significantly compared to the standard drug donepezil, with IC50 values of 7.23 and 7.77 µM, respectively. Molecular docking results indicated that OP compounds have good binding affinity to the α-glucosidase and acetylcholinesterase proteins, making non-bonded interactions with their active residues and surrounding allosteric residues. In addition, none of the compounds violated Lipinski’s rule of five and showed notable toxicity parameters. Density functional theory (DFT)-based global reactivity descriptors demonstrated their high reactive nature along with the kinetic stability. In conclusion, this combined study suggests that OP components might be beneficial in the treatment of inflammation, type 2 diabetes mellitus, and Alzheimer’s disease. Full article
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Open AccessArticle
Binding of Red Clover Isoflavones to Actin as A Potential Mechanism of Anti-Metastatic Activity Restricting the Migration of Cancer Cells
Molecules 2018, 23(10), 2471; https://doi.org/10.3390/molecules23102471 - 26 Sep 2018
Cited by 8
Abstract
Actin functions are crucial for the ability of the cell to execute dynamic cytoskeleton reorganization and movement. Nutraceuticals that form complexes with actin and reduce its polymerization can be used in cancer therapy to prevent cell migration and metastasis of tumors. The aim [...] Read more.
Actin functions are crucial for the ability of the cell to execute dynamic cytoskeleton reorganization and movement. Nutraceuticals that form complexes with actin and reduce its polymerization can be used in cancer therapy to prevent cell migration and metastasis of tumors. The aim of this study was to evaluate the ability of isoflavones to form complexes with actin. Docking simulation and isothermal titration calorimetry were used for this purpose. The formation of complexes by hydrogen bonds, hydrophobic and π-π interactions was demonstrated. Interactions occurred at the ATP binding site, which may limit the rotation of the actin molecule observed during polymerization and also at the site responsible for contacts during polymerization, reducing the ability of the molecule to form filaments. The greatest therapeutic potential was demonstrated by isoflavones occurring in red clover sprouts, i.e., biochanin A and formononetin, being methoxy derivatives of genistein and daidzein. Full article
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Open AccessArticle
Daphnauranins C–E, Three New Antifeedants from Daphne aurantiaca Roots
Molecules 2018, 23(10), 2429; https://doi.org/10.3390/molecules23102429 - 21 Sep 2018
Cited by 1
Abstract
Daphnauranins C–E (compounds 13), two sesquiterpenoids and one monoterpenoid were isolated from the roots of Daphne aurantiaca Diels. Daphnauranin C is a 9-O-13 etherified and hydroperoxy-substituted guaiane sesquiterpenoid, daphnauranin D is a guaiane sesquiterpenoid ketal, and daphnauranin E [...] Read more.
Daphnauranins C–E (compounds 13), two sesquiterpenoids and one monoterpenoid were isolated from the roots of Daphne aurantiaca Diels. Daphnauranin C is a 9-O-13 etherified and hydroperoxy-substituted guaiane sesquiterpenoid, daphnauranin D is a guaiane sesquiterpenoid ketal, and daphnauranin E is a monoterpenoid lactone. Their structures were elucidated by comprehensive analyses of MS, 1D NMR, and 2D NMR spectroscopic data. In an anti-feeding activities test, daphnauranins C–E showed activity against male fruit fly with anti-feeding indexes (AI) up to 39.1, 39.2, and 27.8% respectively, at 1 mM. Full article
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Open AccessFeature PaperArticle
Identification of Bioactive Chemical Markers in Zhi zhu xiang Improving Anxiety in Rat by Fingerprint-Efficacy Study
Molecules 2018, 23(9), 2329; https://doi.org/10.3390/molecules23092329 - 12 Sep 2018
Cited by 3
Abstract
Zhi zhu xiang (ZZX for short) is the root and rhizome of Valeriana jatamansi Jones, which is a Traditional Chinese Medicine (TCM) used to treat various mood disorders for more than 2000 years, especially anxiety. The aim of the present work was to [...] Read more.
Zhi zhu xiang (ZZX for short) is the root and rhizome of Valeriana jatamansi Jones, which is a Traditional Chinese Medicine (TCM) used to treat various mood disorders for more than 2000 years, especially anxiety. The aim of the present work was to identify the bioactive chemical markers in Zhi zhu xiang improving anxiety in rats by a fingerprint-efficacy study. More specifically, the chemical fingerprint of ZZX samples collected from 10 different regions was determined by High Performance Liquid Chromatography (HPLC) and the similarity analyses were calculated based on 10 common characteristic peaks. The anti-anxiety effect of ZZX on empty bottle stimulated rats was examined through the Open Field Test (OFT) and the Elevated Plus Maze Test (EPM). Then we measured the concentration of CRF, ACTH, and CORT in rat’s plasma by the enzyme-linked immune sorbent assay (ELISA) kit, while the concentration of monoamine and metabolites (NE, DA, DOPAC, HVA, 5-HT, 5-HIAA) in the rat’s cerebral cortex and hippocampus was analysed by HPLC coupled with an Electrochemical Detector. At last, the fingerprint-efficacy study between chemical fingerprint and anti-anxiety effect of ZZX was accomplished by partial least squares regression (PLSR). As a result, we screened out four compounds (hesperidin, isochlorogenic acid A, isochlorogenic acid B and isochlorogenic acid C) as the bioactive chemical markers for the anti-anxiety effect of ZZX. The fingerprint-efficacy study we established might provide a feasible way and some elicitation for the identification of the bioactive chemical markers for TCM. Full article
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Open AccessArticle
Phenolic Composition Stability and Antioxidant Activity of Sour Cherry Liqueurs
Molecules 2018, 23(9), 2156; https://doi.org/10.3390/molecules23092156 - 27 Aug 2018
Abstract
The aim of the study was to evaluate changes of phenolic and anthocyanin contents, antioxidant activity, aroma compounds and color of sour cherry liqueurs with and without sugar during 6 months of storage at temperatures of 15 °C and 30 °C. Contents of [...] Read more.
The aim of the study was to evaluate changes of phenolic and anthocyanin contents, antioxidant activity, aroma compounds and color of sour cherry liqueurs with and without sugar during 6 months of storage at temperatures of 15 °C and 30 °C. Contents of phenolic compounds (HPLC, UPLC-MS) and antiradical activity (ABTS) changes were measured. Color changes were measured by an objective method (ColorQuest XE). During storage fluctuations of phenolic compounds and antioxidant activity content were observed. The content of substances which react with Folin-Ciocalteu reagent was comparable before and after 24 weeks. During the 24 weeks of storage, the highest average antioxidant activity against ABTS radicals was shown by sour cherry liqueurs without sugar, stored at 15 °C. Quicker degradation of anthocyanins was observed in liqueurs without sugar, stored at 30 °C (t1/2—5.9 weeks in liqueurs with sugar and 6.6 weeks in liqueurs without sugar). Better stability of red color was observed in liqueurs with sugar, stored at 15 °C. The content of the dominant aroma compound, benzaldehyde, increased during storage. Long-term storage and sugar addition decreases color attributes but increases organoleptic value without of great influence on antioxidant activity. Studies on a half-year period of liqueur storage showed that their characteristic features are almost unchanged if stored at 15 °C and without sugar added, but organoleptic properties were better in samples stored at 30 °C. Full article
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Open AccessArticle
New Naphthalene Derivatives from the Bulbs of Eleutherine americana with Their Protective Effect on the Injury of HUVECs
Molecules 2018, 23(9), 2111; https://doi.org/10.3390/molecules23092111 - 22 Aug 2018
Cited by 3
Abstract
Five new naphthalene derivatives, named Eleutherols A–C (13) and Eleuthinones B–C (4,5), together with three known compounds were isolated from the bulbs of Eleutherine americana. Their structures were elucidated on the basis of spectroscopic [...] Read more.
Five new naphthalene derivatives, named Eleutherols A–C (13) and Eleuthinones B–C (4,5), together with three known compounds were isolated from the bulbs of Eleutherine americana. Their structures were elucidated on the basis of spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR techniques. These compounds exhibited a potent effect against the injury of human umbilical vein endothelial cell (HUVECs) induced by high concentrations of glucose in vitro. Full article
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Open AccessArticle
Phenolic Compounds and Bioactivity of Cytisus villosus Pourr.
Molecules 2018, 23(8), 1994; https://doi.org/10.3390/molecules23081994 - 10 Aug 2018
Cited by 3
Abstract
The present study focuses on the chemical composition, antioxidant, antimicrobial, and antiproliferative activities of the ethyl acetate and aqueous extracts obtained from the aerial parts of Cytisus villosus Pourr. HPLC-DAD-ESI/MSn was used to identify the phenolic compounds, being (epi)gallocatechin dimer the major compound [...] Read more.
The present study focuses on the chemical composition, antioxidant, antimicrobial, and antiproliferative activities of the ethyl acetate and aqueous extracts obtained from the aerial parts of Cytisus villosus Pourr. HPLC-DAD-ESI/MSn was used to identify the phenolic compounds, being (epi)gallocatechin dimer the major compound (111 ± 5 µg/g·dw) in the aqueous extract, while myricetin-O-rhamnoside (226 ± 9 µg/g·dw) was the main molecule in the ethyl acetate extract. Both extracts exhibited good scavenging activities against DPPH radical (EC50 µg/mL of 59 ± 2 and 31 ± 2 for aqueous and ethyl acetate extracts, respectively). However, the ethyl acetate extract demonstrated more potent quenching activities than the aqueous extract. The antimicrobial activities were assessed on selected Gram-positive (Staphylococcus epidermidis) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria, as well as on pathogenic fungus Candida glabrata. The extracts possessed selective and potent antimicrobial activities against the Gram-positive bacterium (IC50 of 186 ± 9 μg/mL and 92 ± 3 μg/mL for aqueous and ethyl acetate extracts, respectively). Finally, C. villosus extracts were evaluated for their antiproliferative potential on three human cancer cell lines representing breast and colon cancers. Although both extracts demonstrated sufficient growth inhibition of the three different cell lines, the ethyl acetate extract exhibited higher activity (LD50 values of 1.57 ± 0.06 mg/mL, 2.2 ± 0.1 mg/mL, and 3.2 ± 0.2 mg/mL for T47D, MCF-7, and HCT-116 cell lines). Both the extracts obtained from the aerial parts of C. villosus revealed very promising results and could be applied as functional agents in the food, pharmaceutical, and cosmeceutical industries. Full article
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Open AccessArticle
The Substituent Effect on the Radical Scavenging Activity of Apigenin
Molecules 2018, 23(8), 1989; https://doi.org/10.3390/molecules23081989 - 10 Aug 2018
Cited by 5
Abstract
Flavonoids widely found in natural foods are excellent free radical scavengers. The relationship between the substituent and antioxidative activity of flavonoids has not yet been completely elucidated. In this work, the antioxidative activity of apigenin derivatives with different substituents at the C3 position [...] Read more.
Flavonoids widely found in natural foods are excellent free radical scavengers. The relationship between the substituent and antioxidative activity of flavonoids has not yet been completely elucidated. In this work, the antioxidative activity of apigenin derivatives with different substituents at the C3 position was determined by density functional theory (DFT) calculations. The bond dissociation enthalpy (BDE), ionization potential (IP), and proton affinity (PA) were calculated. Donator acceptor map (DAM) analysis illustrated that the studied compounds are worse electron acceptors than F and also are not better electron donors than Na. The strongest antioxidative group of apigenin derivatives was the same as apigenin. Excellent correlations were found between the BDE/IP/PA and Hammett sigma constants. Therefore, Hammett sigma constants can be used to predict the antioxidative activity of substituted apigenin and to design new antioxidants based on flavonoids. In non-polar phases, the antioxidative activity of apigenin was increased by the electron-withdrawing groups, while it was reduced by the electron-donating groups. Contrary results occurred in the polar phase. The electronic effect of the substituents on BDE(4′-OH), BDE(5-OH), PA(4′-OH), and IP is mainly controlled by the resonance effect, while that on BDE(7-OH), PA(5-OH), and PA(7-OH) is governed by the field/inductive effect. Full article
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Open AccessArticle
Physicochemical Characterization, Antioxidant and Immunostimulatory Activities of Sulfated Polysaccharides Extracted from Ascophyllum nodosum
Molecules 2018, 23(8), 1912; https://doi.org/10.3390/molecules23081912 - 31 Jul 2018
Cited by 5
Abstract
Polysaccharides from Ascophyllum nodosum (AnPS) were extracted and purified via an optimized protocol. The optimal extraction conditions were as follows: extraction time of 4.3 h, extraction temperature of 84 °C and ratio (v/w, mL/g) of extraction solvent (water) to [...] Read more.
Polysaccharides from Ascophyllum nodosum (AnPS) were extracted and purified via an optimized protocol. The optimal extraction conditions were as follows: extraction time of 4.3 h, extraction temperature of 84 °C and ratio (v/w, mL/g) of extraction solvent (water) to raw material of 27. The resulting yield was 9.15 ± 0.23% of crude AnPS. Two fractions, named AnP1-1 and AnP2-1 with molecular weights of 165.92 KDa and 370.68 KDa, were separated from the crude AnPS by chromatography in DEAE Sepharose Fast Flow and Sephacryl S-300, respectively. AnP1-1 was composed of mannose, ribose, glucuronic acid, glucose and fucose, and AnP2-1 was composed of mannose, glucuronic acid, galactose and fucose. AnPS, AnP1-1 and AnP2-1 exhibited high scavenging activities against ABTS radical and superoxide radical, and showed protective effect on H2O2-induced oxidative injury in RAW264.7 cells. Furthermore, the immunostimulatory activities of AnP1-1 and AnP2-1 were evaluated by Caco-2 cells, the results showed both AnP1-1 and AnP2-1 could significantly promote the production of immune reactive molecules such as interleukin (IL)-8, IL-1β, interferon (IFN)-γ, and tumor necrosis factor (TNF)-α. Therefore, the results suggest that AnPS and its two fractions may be explored as a potential functional food supplement. Full article
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Open AccessArticle
Effects of Linalyl Acetate on Thymic Stromal Lymphopoietin Production in Mast Cells
Molecules 2018, 23(7), 1711; https://doi.org/10.3390/molecules23071711 - 13 Jul 2018
Cited by 3
Abstract
Thymic stromal lymphopoietin (TSLP) is an important factor responsible for the pathogenesis of allergic diseases, such as atopic dermatitis and asthma. Because linalyl acetate (LA) possesses a wide range of pharmacological properties, being antispasmodic, anti-inflammatory, and anti-hyperpigmentation, we hypothesized that LA could inhibit [...] Read more.
Thymic stromal lymphopoietin (TSLP) is an important factor responsible for the pathogenesis of allergic diseases, such as atopic dermatitis and asthma. Because linalyl acetate (LA) possesses a wide range of pharmacological properties, being antispasmodic, anti-inflammatory, and anti-hyperpigmentation, we hypothesized that LA could inhibit TSLP. Therefore, enzyme-linked immunosorbent assay, quantitative polymerase chain reaction, caspase-1 assay, Western blot analysis, fluorescent analyses of the intracellular calcium levels, and the phorbol myristate acetate (PMA)-induced edema model were used to investigate how LA inhibits the production of TSLP in HMC-1 cells. LA reduced the production and mRNA expression of TSLP in HMC-1 cells. LA also inhibited the activation of nuclear factor-κB and degradation of IκBα. PMA plus A23187 stimulation up-regulated caspase-1 activity in HMC-1 cells; however, this up-regulated caspase-1 activity was down-regulated by LA. Finally, LA decreased intracellular calcium levels in HMC-1 cells as well as PMA-induced ear swelling responses in mice. Taken together, these results suggest that LA would be beneficial to treatment of atopic and inflammatory diseases by reducing TSLP. Full article
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Open AccessCommunication
Magnolol Inhibits Osteoclast Differentiation via Suppression of RANKL Expression
Molecules 2018, 23(7), 1598; https://doi.org/10.3390/molecules23071598 - 02 Jul 2018
Cited by 1
Abstract
Magnolol, a compound from the traditional Korean herb Magnolia sp., has been exhaustively investigated as a therapeutic agent against several diseases including systemic and local inflammation. We examined the effects of magnolol on osteoclastic differentiation associated with inflammation. Magnolol markedly reduced interleukin (IL)-1-induced [...] Read more.
Magnolol, a compound from the traditional Korean herb Magnolia sp., has been exhaustively investigated as a therapeutic agent against several diseases including systemic and local inflammation. We examined the effects of magnolol on osteoclastic differentiation associated with inflammation. Magnolol markedly reduced interleukin (IL)-1-induced osteoclast formation in co-cultures of murine osteoblasts and bone marrow cells, whereas it had no effect on receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclast formation in bone marrow macrophage cultures. In osteoblasts, magnolol markedly inhibited both the up-regulation of RANKL expression and the production of prostaglandin E2 (PGE2) in response to IL-1 treatment. Addition of exogenous PGE2 reversed the inhibitory effects of magnolol on IL-1-induced RANKL expression in osteoblasts and osteoclast formation in co-cultures. Magnolol inhibited IL-1-induced PGE2 production, at least in part by suppressing cyclooxygenase-2 (COX-2) expression. Taken together, these results demonstrate that magnolol inhibits IL-1-induced RANKL expression in osteoblasts through suppression of COX-2 expression and PGE2 production, resulting in inhibition of osteoclast differentiation in co-cultures. Full article
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Open AccessReview
Cosmetics Preservation: A Review on Present Strategies
Molecules 2018, 23(7), 1571; https://doi.org/10.3390/molecules23071571 - 28 Jun 2018
Cited by 23
Abstract
Cosmetics, like any product containing water and organic/inorganic compounds, require preservation against microbial contamination to guarantee consumer’s safety and to increase their shelf-life. The microbiological safety has as main goal of consumer protection against potentially pathogenic microorganisms, together with the product’s preservation resulting [...] Read more.
Cosmetics, like any product containing water and organic/inorganic compounds, require preservation against microbial contamination to guarantee consumer’s safety and to increase their shelf-life. The microbiological safety has as main goal of consumer protection against potentially pathogenic microorganisms, together with the product’s preservation resulting from biological and physicochemical deterioration. This is ensured by chemical, physical, or physicochemical strategies. The most common strategy is based on the application of antimicrobial agents, either by using synthetic or natural compounds, or even multifunctional ingredients. Current validation of a preservation system follow the application of good manufacturing practices (GMPs), the control of the raw material, and the verification of the preservative effect by suitable methodologies, including the challenge test. Among the preservatives described in the positive lists of regulations, there are parabens, isothiasolinone, organic acids, formaldehyde releasers, triclosan, and chlorhexidine. These chemical agents have different mechanisms of antimicrobial action, depending on their chemical structure and functional group’s reactivity. Preservatives act on several cell targets; however, they might present toxic effects to the consumer. Indeed, their use at high concentrations is more effective from the preservation viewpoint being, however, toxic for the consumer, whereas at low concentrations microbial resistance can develop. Full article
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Open AccessArticle
(−)-Epicatechin Reduces Blood Pressure and Improves Left Ventricular Function and Compliance in Deoxycorticosterone Acetate-Salt Hypertensive Rats
Molecules 2018, 23(7), 1511; https://doi.org/10.3390/molecules23071511 - 22 Jun 2018
Cited by 8
Abstract
(−)-Epicatechin (E) is a flavanol found in green tea and cocoa and has been shown to attenuate tumour necrosis factor alpha (TNF-α)-mediated inflammation, improve nitric oxide levels, promote endothelial nitric oxide synthase (eNOS) activation and inhibit NADPH oxidase. This study investigated [...] Read more.
(−)-Epicatechin (E) is a flavanol found in green tea and cocoa and has been shown to attenuate tumour necrosis factor alpha (TNF-α)-mediated inflammation, improve nitric oxide levels, promote endothelial nitric oxide synthase (eNOS) activation and inhibit NADPH oxidase. This study investigated the effect of 28 days of low epicatechin dosing (1 mg/kg/day) on the cardiovascular function of deoxycorticosterone acetate (DOCA)-salt hypertensive rats. Wistar rats (n = 120, 8 weeks of age) underwent uninephrectomy and were randomised into four groups (uninephrectomy (UNX), UNX + E, DOCA, DOCA + E). DOCA and DOCA + E rats received 1% NaCl drinking water along with subcutaneous injections of 25 mg deoxycorticosterone-acetate (in 0.4 mL of dimethylformamide) every fourth day. UNX + E and DOCA + E rats received 1 mg/kg/day of epicatechin by oral gavage. Single-cell micro-electrode electrophysiology, Langendorff isolated-heart assessment and isolated aorta and mesenteric organ baths were used to assess cardiovascular parameters. Serum malondialdehyde concentration was used as a marker of oxidative stress. Myocardial stiffness was increased and left ventricular compliance significantly diminished in the DOCA control group, and these changes were attenuated by epicatechin treatment (p < 0.05). Additionally, the DOCA + E rats showed significantly reduced blood pressure and malondialdehyde concentrations; however, there was no improvement in left ventricular hypertrophy, electrophysiology or vascular function. This study demonstrates the ability of epicatechin to reduce blood pressure, prevent myocardial stiffening and preserve cardiac compliance in hypertrophied DOCA-salt rat hearts. Full article
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Open AccessArticle
Pentacyclic Triterpenes from Cecropia telenitida Can Function as Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1
Molecules 2018, 23(6), 1444; https://doi.org/10.3390/molecules23061444 - 14 Jun 2018
Cited by 5
Abstract
Plant extracts from the genus Cecropia have been used by Latin-American traditional medicine to treat metabolic disorders and diabetes. Previous results have shown that roots of Cecropia telenitida contain pentacyclic triterpenes and these molecules display a hypoglycemic effect in an insulin-resistant murine model. [...] Read more.
Plant extracts from the genus Cecropia have been used by Latin-American traditional medicine to treat metabolic disorders and diabetes. Previous results have shown that roots of Cecropia telenitida contain pentacyclic triterpenes and these molecules display a hypoglycemic effect in an insulin-resistant murine model. The pharmacological target of these molecules, however, remains unknown. Several lines of evidence indicate that pentacyclic triterpenes inhibit the 11β-hydroxysteroid dehydrogenase type 1 enzyme, which highlights the potential use of this type of natural product as phytotherapeutic or botanical dietary supplements. The main goal of the study was the evaluation of the inhibitory effect of Cecropia telenitida molecules on 11β-hydroxysteroid dehydrogenase type 1 enzyme activity. A pre-fractionated chemical library was obtained from the roots of Cecropia telenitida using several automated chromatography separation steps and a homogeneous time resolved fluorescence assay was used for the bio-guided isolation of inhibiting molecules. The screening of a chemical library consisting of 125 chemical purified fractions obtained from Cecropia telenitida roots identified one fraction displaying 82% inhibition of the formation of cortisol by the 11β-hydroxysteroid dehydrogenase type 1 enzyme. Furthermore, a molecule displaying IC50 of 0.95 ± 0.09 µM was isolated from this purified fraction and structurally characterized, which confirms that a pentacyclic triterpene scaffold was responsible for the observed inhibition. Our results support the hypothesis that pentacyclic triterpene molecules from Cecropia telenitida can inhibit 11β-hydroxysteroid dehydrogenase type 1 enzyme activity. These findings highlight the potential ethnopharmacological use of plants from the genus Cecropia for the treatment of metabolic disorders and diabetes. Full article
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Open AccessArticle
Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus
Molecules 2018, 23(6), 1336; https://doi.org/10.3390/molecules23061336 - 01 Jun 2018
Cited by 2
Abstract
Sterepinic acids A–C (13), new carboxylic acids with two primary alcohols, have been isolated from a fungal strain of Stereum sp. OUPS-124D-1 attached to the marine alga Undaria pinnatifida. Dihydro-1,5-secovibralactone (4), a new vibralactone derivative, was [...] Read more.
Sterepinic acids A–C (13), new carboxylic acids with two primary alcohols, have been isolated from a fungal strain of Stereum sp. OUPS-124D-1 attached to the marine alga Undaria pinnatifida. Dihydro-1,5-secovibralactone (4), a new vibralactone derivative, was isolated from the same fungal metabolites together with known vibralactone A (5), and 1,5-secovibralactone (6). The planar structures of these compounds have been elucidated by spectroscopic analyses using IR, HRFABMS, and NMR spectra. To determine the absolute configuration of the compounds, we used the phenylglycine methyl ester (PGME) method. These compounds exhibited less activity in the cytotoxicity assay against cancer cell lines. Full article
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Open AccessArticle
Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
Molecules 2018, 23(6), 1291; https://doi.org/10.3390/molecules23061291 - 28 May 2018
Cited by 7
Abstract
Aspergoterpenins A–D (14), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (512), and their structures were elucidated by a comprehensive analysis of their [...] Read more.
Aspergoterpenins A–D (14), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (512), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 112 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 112 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL. Full article
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Open AccessArticle
Four New Lignans from Kadsura Interior and Their Bioactivity
Molecules 2018, 23(6), 1279; https://doi.org/10.3390/molecules23061279 - 26 May 2018
Abstract
A phytochemical investigation of the stems of Kadsura interior has led to an isolation of four new lignans, named kadsutherin E–H (14), together with two known lignans (56). The structures of the four new compounds [...] Read more.
A phytochemical investigation of the stems of Kadsura interior has led to an isolation of four new lignans, named kadsutherin E–H (14), together with two known lignans (56). The structures of the four new compounds were established on the basis of comprehensive spectroscopic analyses. Compounds 16 exhibited inhibition against adenosine diphosphate (ADP) induced platelet aggregation. Among the isolated compounds, kadsutherin F (2) showed the strongest anti-platelet aggregation activity with an inhibition of 49.47%. Full article
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Open AccessFeature PaperCommunication
Antioxidants from the Brown Alga Dictyopteris undulata
Molecules 2018, 23(5), 1214; https://doi.org/10.3390/molecules23051214 - 18 May 2018
Cited by 4
Abstract
An investigation of anti-oxidative compounds from the brown alga Dictyopteris undulata has led to the isolation and identification of isozonarol, isozonarone, chromazonarol, zonaroic acid and isozonaroic acid. Their structures were identified by comparison of MS and NMR spectra. Full NMR assignment and absolute [...] Read more.
An investigation of anti-oxidative compounds from the brown alga Dictyopteris undulata has led to the isolation and identification of isozonarol, isozonarone, chromazonarol, zonaroic acid and isozonaroic acid. Their structures were identified by comparison of MS and NMR spectra. Full NMR assignment and absolute configuration of isozonaroic acid are described. Isozonarol showed the most potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity among the compounds isolated. Full article
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Open AccessReview
Echinacoside, an Inestimable Natural Product in Treatment of Neurological and other Disorders
Molecules 2018, 23(5), 1213; https://doi.org/10.3390/molecules23051213 - 18 May 2018
Cited by 9
Abstract
Echinacoside (ECH), a natural phenylethanoid glycoside, was first isolated from Echinacea angustifolia DC. (Compositae) sixty years ago. It was found to possess numerous pharmacologically beneficial activities for human health, especially the neuroprotective and cardiovascular effects. Although ECH showed promising potential for treatment of [...] Read more.
Echinacoside (ECH), a natural phenylethanoid glycoside, was first isolated from Echinacea angustifolia DC. (Compositae) sixty years ago. It was found to possess numerous pharmacologically beneficial activities for human health, especially the neuroprotective and cardiovascular effects. Although ECH showed promising potential for treatment of Parkinson’s and Alzheimer’s diseases, some important issues arose. These included the identification of active metabolites as having poor bioavailability in prototype form, the definite molecular signal pathways or targets of ECH with the above effects, and limited reliable clinical trials. Thus, it remains unresolved as to whether scientific research can reasonably make use of this natural compound. A systematic summary and knowledge of future prospects are necessary to facilitate further studies for this natural product. The present review generalizes and analyzes the current knowledge on ECH, including its broad distribution, different preparation technologies, poor pharmacokinetics and kinds of therapeutic uses, and the future perspectives of its potential application. Full article
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Open AccessArticle
Identification of Insecticidal Constituents from the Essential Oil from the Aerial Parts Stachys riederi var. japonica
Molecules 2018, 23(5), 1200; https://doi.org/10.3390/molecules23051200 - 17 May 2018
Cited by 4
Abstract
The essential oil of Stachys riederi var. japonica (Family: Lamiaceae) was extracted by hydrodistillation and determined by GC and GC-MS. A total of 40 components were identified, representing 96.01% of the total oil composition. The major compounds in the essential oil were acetanisole [...] Read more.
The essential oil of Stachys riederi var. japonica (Family: Lamiaceae) was extracted by hydrodistillation and determined by GC and GC-MS. A total of 40 components were identified, representing 96.01% of the total oil composition. The major compounds in the essential oil were acetanisole (15.43%), anisole (9.43%), 1,8-cineole (8.07%), geraniol (7.89%), eugenol (4.54%), caryophyllene oxide (4.47%), caryophyllene (4.21%) and linalool (4.07%). Five active constituents (acetanisole, anisole, 1,8-cineole, eugenol and geraniol) were identified by bioactivity-directed fractionation. The essential oil possessed fumigant toxicity against maize weevils (Sitophilus zeamais) and booklice (Liposcelis bostrychophila), with LC50 values of 15.0 mg/L and 0.7 mg/L, respectively. Eugenol and anisole exhibited stronger fumigant toxicity than the oil against booklice. 1,8-Cineole showed stronger toxicity, and anisole as well as eugenol exhibited the same level of fumigant toxicity as the essential oil against maize weevils. The essential oil also exhibited contact toxicity against S. zeamais adults and L. bostrychophila, with LC50 values of 21.8 µg/adult and 287.0 µg/cm2, respectively. The results indicated that the essential oil of S. riederi var. japonica and its isolates show potential as fumigants, and for their contact toxicity against grain storage insects. Full article
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Open AccessArticle
Pyrrole Alkaloids from the Edible Mushroom Phlebopus portentosus with Their Bioactive Activities
Molecules 2018, 23(5), 1198; https://doi.org/10.3390/molecules23051198 - 17 May 2018
Cited by 2
Abstract
Seven pyrrole alkaloids, three of which are novel (phlebopines A–C (13)), were isolated from the fruiting bodies of the edible mushroom Phlebopus portentosus. Their structures were determined on the basis of spectroscopic data. All the isolated compounds were [...] Read more.
Seven pyrrole alkaloids, three of which are novel (phlebopines A–C (13)), were isolated from the fruiting bodies of the edible mushroom Phlebopus portentosus. Their structures were determined on the basis of spectroscopic data. All the isolated compounds were tested for their neuroprotective properties and acetylcholine esterase (AChE) inhibition activities. Compound 7 displayed remarkable neuroprotective effects against hydrogen peroxide (H2O2)-induced neuronal-cell damage in human neuroblastoma SH-SY5Y cells. Full article
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Open AccessArticle
Study on the Polar Extracts of Dendrobium nobile, D. officinale, D. loddigesii, and Flickingeria fimbriata: Metabolite Identification, Content Evaluation, and Bioactivity Assay
Molecules 2018, 23(5), 1185; https://doi.org/10.3390/molecules23051185 - 15 May 2018
Cited by 4
Abstract
The polar extract of the Dendrobium species or F. fimbriata (a substitute of Dendrobium), between the fat-soluble extract and polysaccharide has barely been researched. This report worked on the qualitative and quantitative studies of polar extracts from D. nobile, D. officinale [...] Read more.
The polar extract of the Dendrobium species or F. fimbriata (a substitute of Dendrobium), between the fat-soluble extract and polysaccharide has barely been researched. This report worked on the qualitative and quantitative studies of polar extracts from D. nobile, D. officinale, D. loddigesii, and F. fimbriata. Eight water-soluble metabolites containing a new diglucoside, flifimdioside A (1), and a rare imidazolium-type al