Molecules

15 pages, 4549 KiB

Open AccessArticle

Euodia daniellii Hemsl. Extract and Its Active Component Hesperidin Accelerate Cutaneous Wound Healing via Activation of Wnt/β-Catenin Signaling Pathway

by Minguen Yoon, Seol Hwa Seo, Seonghwi Choi, Gyoonhee Han and Kang-Yell Choi

Molecules 2022, 27(20), 7134; https://doi.org/10.3390/molecules27207134 - 21 Oct 2022

Cited by 9 | Viewed by 2369

Abstract

The activation of the Wnt/β-catenin signaling pathway plays a key role in the wound-healing process through tissue regeneration. The extract of Euodia daniellii Hemsl. (E. daniellii), a member of the Rutaceae family, activates the Wnt/β-catenin signaling pathway. However, the function of [...] Read more.

The activation of the Wnt/β-catenin signaling pathway plays a key role in the wound-healing process through tissue regeneration. The extract of Euodia daniellii Hemsl. (E. daniellii), a member of the Rutaceae family, activates the Wnt/β-catenin signaling pathway. However, the function of E. daniellii in wound healing has not yet been elucidated. We performed a migration assay to determine the wound-healing effect of E. daniellii extract in vitro using human keratinocytes and dermal fibroblast. In addition, a mouse acute wound model was used to investigate the cutaneous wound-healing effect of E. daniellii extract in vivo and confirm the potential mechanism. E. daniellii extract enhanced the migration of human keratinocytes and dermal fibroblasts via the activation of the Wnt/β-catenin pathway. Moreover, the E. daniellii extract increased the levels of keratin 14, PCNA, collagen I, and α-SMA, with nuclei accumulation of β-catenin in vitro. E. daniellii extract also efficiently accelerated re-epithelialization and stimulated wound healing in vivo. Furthermore, we confirmed that hesperidin, one of the components of E. daniellii, efficiently accelerated the migration of human keratinocytes and dermal fibroblasts, as well as wound healing in vivo via the activation of the Wnt/β-catenin pathway. Overall, E. daniellii extract and its active component, hesperidin, have potential to be used as therapeutic agents for wound healing. Full article

(This article belongs to the Special Issue Novel Natural Compounds as Wound Healing Agents)

► Show Figures

Figure 1

17 pages, 2208 KiB

Open AccessArticle

Volatile Organic Compound Profiles of Cystoseira corniculata (Turner) Zanardini 1841 and Ericaria amentacea (C.Agardh) Molinari and Guiry 2020 (ex. Cystoseira amentacea (C.Agardh) Bory de Saint-Vincent, 1832)

by Sanja Radman and Igor Jerković

Molecules 2022, 27(20), 7131; https://doi.org/10.3390/molecules27207131 - 21 Oct 2022

Cited by 5 | Viewed by 1765

Abstract

The volatile organic compounds (VOCs) of fresh (FrCC) and air-dried (DrCC) Cystoseria corniculata and fresh (FrEA) and air-dried (DrEA) Ericaria amentacea from the Adriatic Sea were investigated by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and analysed by gas chromatography and mass spectrometry [...] Read more.

The volatile organic compounds (VOCs) of fresh (FrCC) and air-dried (DrCC) Cystoseria corniculata and fresh (FrEA) and air-dried (DrEA) Ericaria amentacea from the Adriatic Sea were investigated by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and analysed by gas chromatography and mass spectrometry (GC-MS). In HS-FrCC and HS-DrCC, aliphatic compounds were dominant, with decan-5-ol as the most abundant in HS-FrCC, but in HS-DrCC pentadecane dominated. Monoterpenes (β-cyclocitral, β-citral, and β-cyclohomocitral) and sesquiterpenes (cubenol) were abundant in HS-FrCC. Notable differences between fresh and air-dried samples were found for benzene derivatives. Fatty acids and their derivatives were the most abundant in HD-FrCC and HD-DrCC. In HS-FrEA and HS-DrEA, saturated aliphatic compounds as well as unsaturated aliphatic compounds (particularly hexan-1-ol and (Z)-hex-3-en-1-ol) predominantly showed decrements after drying. Pentadecane, heptadecane, pentadecanal, and hexan-1-ol were predominant in HD-FrEA, and their percentage decreased in HD-DrEA. The percentage of monoterpenes decreased after drying, but the percentages of diterpenes and especially sesquiterpenes increased. δ-Selinene was the major terpene and the most abundant in HD-DrEA. A significant increment after drying could be noticed for fatty acids and their derivatives. The great diversity of identified VOCs among these two macroalgae supports their different botanical classifications. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

► Show Figures

Figure 1

13 pages, 8334 KiB

Open AccessArticle

Synthesis, In Vitro Anti-Microbial Analysis and Molecular Docking Study of Aliphatic Hydrazide-Based Benzene Sulphonamide Derivatives as Potent Inhibitors of α-Glucosidase and Urease

by Shoaib Khan, Shahid Iqbal, Mazloom Shah, Wajid Rehman, Rafaqat Hussain, Liaqat Rasheed, Hamad Alrbyawi, Ayed A. Dera, Mohammed Issa Alahmdi, Rami Adel Pashameah, Eman Alzahrani and Abd-ElAziem Farouk

Molecules 2022, 27(20), 7129; https://doi.org/10.3390/molecules27207129 - 21 Oct 2022

Cited by 20 | Viewed by 2789

Abstract

A unique series of sulphonamide derivatives was attempted to be synthesized in this study using a new and effective method. All of the synthesized compounds were verified using several spectroscopic methods, including FTIR, ¹H-NMR, ¹³C-NMR, and HREI-MS, and their binding interactions [...] Read more.

A unique series of sulphonamide derivatives was attempted to be synthesized in this study using a new and effective method. All of the synthesized compounds were verified using several spectroscopic methods, including FTIR, ¹H-NMR, ¹³C-NMR, and HREI-MS, and their binding interactions were studied using molecular docking. The enzymes urease and α-glucosidase were evaluated against each derivative (1–15). When compared to their respective standard drug such as acarbose and thiourea, almost all compounds were shown to have excellent activity. Among the screened series, analogs 5 (IC₅₀ = 3.20 ± 0.40 and 2.10 ± 0.10 µM) and 6 (IC₅₀ = 2.50 ± 0.40 and 5.30 ± 0.20 µM), emerged as potent molecules when compared to the standard drugs acarbose (IC₅₀ = 8.24 ± 0.08 µM) and urease (IC₅₀ = 7.80 ± 0.30). Moreover, an anti-microbial study also demonstrated that analogs 5 and 6 were found with minimum inhibitory concentrations (MICs) in the presence of standard drugs streptomycin and terinafine. Full article

(This article belongs to the Special Issue Probing Pharmacological and Biological Performance of Synthetic and Natural Compounds)

► Show Figures

Figure 1

21 pages, 2167 KiB

Open AccessArticle

Understanding the Antilymphoma Activity of Annona macroprophyllata Donn and Its Acyclic Terpenoids: In Vivo, In Vitro, and In Silico Studies

by Jesica Ramírez-Santos, Fernando Calzada, Jessica Elena Mendieta-Wejebe, Rosa María Ordoñez-Razo, Rubria Marlen Martinez-Casares and Miguel Valdes

Molecules 2022, 27(20), 7123; https://doi.org/10.3390/molecules27207123 - 21 Oct 2022

Cited by 7 | Viewed by 2515

Abstract

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as [...] Read more.

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as antilymphoma agents. We identified the terpenoids farnesyl acetate (FA), phytol (PT) and geranylgeraniol (Gg) using gas chromatography–mass spectroscopy (GC-MS) and spectroscopic (¹H, and ¹³C NMR) methods applied to petroleum ether extract of leaves from A. macroprophyllata (PEAm). We investigated antitumor potential in Balb/c mice inoculated with U-937 cells by assessing brine shrimp lethality (BSL), and cytotoxic activity in these cells. In addition, to assess the potential toxicity of PEAm, FA, PT and Gg in humans, we tested their acute oral toxicity in mice. Our results showed that the three terpenoids exhibited considerable antilymphoma and cytotoxic activity. In terms of lethality, we determined a median lethal dose (LD₅₀) for thirteen isolated products of PEAm. Gg, PT and AF all exhibited a higher lethality with values of 1.41 ± 0.42, 3.03 ± 0.33 and 5.82 ± 0.58 µg mL⁻¹, respectively. To assess cytotoxic activity against U-937 cells, we calculated the mean cytotoxic concentration (CC₅₀) and found that FA and PT were closer in respect to the control drug methotrexate (MTX, 0.243 ± 0.007 µM). In terms of antilymphoma activity, we found that FA, PT and Gg considerably inhibited lymph node growth, with median effective doses (ED₅₀) of 5.89 ± 0.39, 6.71 ± 0.31 and 7.22 ± 0.51 mg kg⁻¹ in females and 5.09 ± 0.66, 5.83 ± 0.50 and 6.98 ± 0.57mg kg ⁻¹ in males, respectively. Regarding acute oral toxicity, we classified all three terpenoids as category IV, indicating a high safety margin for human administration. Finally, in a molecular docking study of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, we found binding of terpenoids to some amino acids of the catalytic site, suggesting an effect upon activity with a resulting decrease in the synthesis of intermediates involved in the prenylation of proteins involved in cancer progression. Our findings suggest that the acyclic terpenoids FA, PT, and Gg may serve as scaffolds for the development of new treatments for non-Hodgkin’s lymphoma. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

► Show Figures

Figure 1

15 pages, 3085 KiB

Open AccessArticle

The Amomum tsao-ko Essential Oils Inhibited Inflammation and Apoptosis through p38/JNK MAPK Signaling Pathway and Alleviated Gentamicin-Induced Acute Kidney Injury

by Xiu-Jun Xu, Mei-Ling Zhang, Yan-Min Hou, Ke Zhang, Da-Hong Yao, Guo-Yu Li, Wei-Bing Kou, Hang-Yu Wang and Jin-Hui Wang

Molecules 2022, 27(20), 7121; https://doi.org/10.3390/molecules27207121 - 21 Oct 2022

Cited by 10 | Viewed by 3252

Abstract

The clinical application of gentamicin may lead to acute kidney injury (AKI), and the nephrotoxicity of gentamicin is related to the pathological mechanism of several oxidative and inflammatory cytokines. Plant-derived essential oils have good anti-inflammatory and antioxidant properties. This study aimed to clarify [...] Read more.

The clinical application of gentamicin may lead to acute kidney injury (AKI), and the nephrotoxicity of gentamicin is related to the pathological mechanism of several oxidative and inflammatory cytokines. Plant-derived essential oils have good anti-inflammatory and antioxidant properties. This study aimed to clarify the protective effect of Amomum tsao-ko essential oils (AOs) on gentamicin-induced AKI in rats and its possible mechanism. The rat AKI model was induced by intraperitoneal injection of gentamicin. After 14 days of oral AO treatment, the renal function and pathological changes of the kidney tissues were evaluated, and the level of kidney tissue oxidative stress was detected. The content of inflammatory cytokines was measured by ELISA. The expression of ERK1/2, JNK1/2, p38, NF-κB, caspase-3, and Bax/Bcl-2 proteins were estimated by Western blot analysis. The results showed that taking AO reduced the contents of serum urea and creatinine in AKI rats and improve the pathological changes and oxidative stress of the kidney tissue in rats. At the same time, AO reduced inflammation and apoptosis during AKI by regulating the MAPK pathway. The data show that AO has a protective effect on the kidneys and may be a potential drug for treating kidney injury. Full article

(This article belongs to the Section Natural Products Chemistry)

► Show Figures

Figure 1

12 pages, 692 KiB

Open AccessArticle

Phytochemical Composition and In Vitro Antioxidant, Anti-Inflammatory, Anticancer, and Enzyme-Inhibitory Activities of Artemisia nilagirica (C.B. Clarke) Pamp

by Jawaher J. Albaqami, Tancia P. Benny, Hamida Hamdi, Ammar B. Altemimi, Aswathi Moothakoottil Kuttithodi, Joice Tom Job, Anju Sasidharan and Arunaksharan Narayanankutty

Molecules 2022, 27(20), 7119; https://doi.org/10.3390/molecules27207119 - 21 Oct 2022

Cited by 5 | Viewed by 2994

Abstract

Plants have been employed in therapeutic applications against various infectious and chronic diseases from ancient times. Various traditional medicines and folk systems have utilized numerous plants and plant products, which act as sources of drug candidates for modern medicine. Artemisia is a genus [...] Read more.

Plants have been employed in therapeutic applications against various infectious and chronic diseases from ancient times. Various traditional medicines and folk systems have utilized numerous plants and plant products, which act as sources of drug candidates for modern medicine. Artemisia is a genus of the Asteraceae family with more than 500 species; however, many of these species are less explored for their biological efficacy, and several others are lacking scientific explanations for their uses. Artemisia nilagirica is a plant that is widely found in the Western Ghats, Kerala, India and is a prominent member of the genus. In the current study, the phytochemical composition and the antioxidant, enzyme-inhibitory, anti-inflammatory, and anticancer activities were examined. The results indicated that the ethanol extract of A. nilagirica indicated in vitro DPPH scavenging (23.12 ± 1.28 µg/mL), ABTS scavenging (27.44 ± 1.88 µg/mL), H₂O₂ scavenging (12.92 ± 1.05 µg/mL), and FRAP (5.42 ± 0.19 µg/mL). The anti-inflammatory effect was also noticed in the Raw 264.7 macrophages, where pretreatment with the extract reduced the LPS-stimulated production of cytokines (p < 0.05). A. nilagirica was also efficient in inhibiting the activities of α-amylase (38.42 ± 2.71 µg/mL), α-glucosidase (55.31 ± 2.16 µg/mL), aldose reductase (17.42 ± 0.87 µg/mL), and sorbitol dehydrogenase (29.57 ± 1.46 µg/mL). It also induced significant inhibition of proliferation in breast (MCF7 IC₅₀ = 41.79 ± 1.07, MDAMB231 IC₅₀ = 55.37 ± 2.11µg/mL) and colon (49.57 ± 1.46 µg/mL) cancer cells. The results of the phytochemical screening indicated a higher level of polyphenols and flavonoids in the extract and the LCMS analysis revealed the presence of various bioactive constituents including artemisinin. Full article

(This article belongs to the Special Issue Natural Bioactive Compounds and Human Health)

► Show Figures

Figure 1

12 pages, 3777 KiB

Open AccessArticle

Identification of Natural Compounds as Inhibitors of Pyruvate Kinase M2 for Cancer Treatment

by Iqra Sarfraz, Azhar Rasul, Farhat Jabeen, Tayyaba Sultana and Şevki Adem

Molecules 2022, 27(20), 7113; https://doi.org/10.3390/molecules27207113 - 21 Oct 2022

Cited by 7 | Viewed by 3960

Abstract

The reliance of tumor cells on aerobic glycolysis is one of the emerging hallmarks of cancer. Pyruvate kinase M2 (PKM2), an important enzyme of glycolytic pathway, is highly expressed in a number of cancer cells. Tumor cells heavily depend on PKM2 to fulfill [...] Read more.

The reliance of tumor cells on aerobic glycolysis is one of the emerging hallmarks of cancer. Pyruvate kinase M2 (PKM2), an important enzyme of glycolytic pathway, is highly expressed in a number of cancer cells. Tumor cells heavily depend on PKM2 to fulfill their divergent energetic and biosynthetic requirements, suggesting it as novel drug target for cancer therapies. Based on this context, we performed enzymatic-assay-based screening of the in-house phenolic compounds library for the identification of PKM2 inhibitors. This screening identified silibinin, curcumin, resveratrol, and ellagic acid as potential inhibitors of PKM2 with IC₅₀ values of 0.91 µM, 1.12 µM, 3.07 µM, and 4.20 µM respectively. For the determination of Ki constants and the inhibition type of hit compounds, Lineweaver–Burk graphs were plotted. Silibinin and ellagic acid performed the competitive inhibition of PKM2 with Ki constants of 0.61 µM and 5.06 µM, while curcumin and resveratrol were identified as non-competitive inhibitors of PKM2 with Ki constants of 1.20 µM and 7.34 µM. The in silico screening of phenolic compounds against three binding sites of PKM2 provided insight into the binding pattern and functionally important amino residues of PKM2. Further, the evaluation of cytotoxicity via MTT assay demonstrated ellagic acid as potent inhibitor of cancer cell growth (IC₅₀ = 20 µM). These results present ellagic acid, silibinin, curcumin, and resveratrol as inhibitors of PKM2 to interrogate metabolic reprogramming in cancer cells. This study has also provided the foundation for further research to validate the potential of identified bioactive entities for PKM2 targeted-cancer therapies. Full article

(This article belongs to the Special Issue Bioactive Compounds in Food Bioscience and Pharmacology)

► Show Figures

Figure 1

14 pages, 3113 KiB

Open AccessArticle

Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of Myrtus communis against Staphylococcus Species

by Francesca Guzzo, Alexandra G. Durán, Cinzia Sanna, Rosangela Marasco, Nicola Molfetta, Elisabetta Buommino, Antonio Fiorentino and Brigida D’Abrosca

Molecules 2022, 27(20), 7109; https://doi.org/10.3390/molecules27207109 - 21 Oct 2022

Cited by 3 | Viewed by 2337

Abstract

Myrtaceae family is a continuous source of antimicrobial agents. In the search for novel antimicrobial agents against Staphylococcus species, bioactive fractions of Myrtus communis L., growing in the Sardinia island (Italy) have been investigated. Their phytochemical analysis led us to isolate and characterize [...] Read more.

Myrtaceae family is a continuous source of antimicrobial agents. In the search for novel antimicrobial agents against Staphylococcus species, bioactive fractions of Myrtus communis L., growing in the Sardinia island (Italy) have been investigated. Their phytochemical analysis led us to isolate and characterize four alkylphloroglucinol glycosides (1–4), three of them gallomyrtucommulones G–H (1,2), and myrtucommulonoside (4) isolated and characterized for the first time. The structures of the new and known compounds, endopreroxide G3 (5), myricetin-3-O-glycosides (6,7) were determined based on the spectroscopic evidence including 1D-/2D-NMR and HR-MS spectrometry. Enriched fractions as well as pure compounds were tested for their antimicrobial activity by broth micro-dilution assay against Staphylococcus epidermidis and S. aureus. Results reported herein demonstrated that gallomyrtucommulone G (1) showed a selective antimicrobial activity against both S. aureus strains (ATCC 29213 and 43300) until 16 μg/mL while gallomyrtucommulone D (3) showed the best growth inhibition value at 64 μg/mL. Full article

(This article belongs to the Section Natural Products Chemistry)

► Show Figures

Figure 1

16 pages, 2781 KiB

Open AccessArticle

Antioxidant and Biological Activities of the Lotus Root Polysaccharide-Iron (III) Complex

by Shuai Yuan, Pei-Yu Dong, Hao-Hai Ma, Sheng-Lin Liang, Long Li and Xi-Feng Zhang

Molecules 2022, 27(20), 7106; https://doi.org/10.3390/molecules27207106 - 21 Oct 2022

Cited by 20 | Viewed by 3307

Abstract

In this study, the synthesis parameters of the lotus root polysaccharide iron complex (LRPF) were determined and optimized by response surface methodology. Under the optimum preparation conditions, the pH of the solution was 9, the ratio of M (trisodium citrate): m (lotus root [...] Read more.

In this study, the synthesis parameters of the lotus root polysaccharide iron complex (LRPF) were determined and optimized by response surface methodology. Under the optimum preparation conditions, the pH of the solution was 9, the ratio of M (trisodium citrate): m (lotus root polysaccharide) was 0.45, the reaction time was 3 h. UV spectroscopy, thermogravimetry, FT-IR spectroscopy, X-ray diffraction, CD, and NMR were used for the characterization of the LRPF. LRPF has good stability and easily releases iron ions under artificial gastrointestinal conditions. LRPF exhibited antioxidant activity in vitro and can significantly improve the antioxidant activity in vivo. In addition, LRPF has a good effect in the treatment of iron deficiency anemia in model mice, impacts the gut microbiome, and reduces the iron deficiency-induced perniciousness by regulating steroid hormone biosynthesis. Therefore, LRPF can be used as a nutritional supplement to treat and prevent iron-deficiency anemia and improve human immunity. Full article

(This article belongs to the Special Issue Key Role of Natural Bioactive Compounds in Health and Diseases)

► Show Figures

Figure 1

25 pages, 1882 KiB

Open AccessFeature PaperArticle

Anticholinesterase Activity of Selected Medicinal Plants from Navarra Region of Spain and a Detailed Phytochemical Investigation of Origanum vulgare L. ssp. vulgare

by María Pilar de Torre, Rita Yolanda Cavero and María Isabel Calvo

Molecules 2022, 27(20), 7100; https://doi.org/10.3390/molecules27207100 - 20 Oct 2022

Cited by 14 | Viewed by 3504

Abstract

Alzheimer’s disease is a neurodegenerative disease characterized by progressive memory loss and cognitive impairment due to a severe loss of cholinergic neurons in specific brain areas. It is the most common type of dementia in the aging population. Although many anti-acetylcholinesterase (AChE) drugs [...] Read more.

Alzheimer’s disease is a neurodegenerative disease characterized by progressive memory loss and cognitive impairment due to a severe loss of cholinergic neurons in specific brain areas. It is the most common type of dementia in the aging population. Although many anti-acetylcholinesterase (AChE) drugs are already available on the market, their performance sometimes yields unexpected results. For this reason, research works are ongoing to find potential anti-AChE agents both from natural and synthetic sources. In this study, 90 extracts from 30 native and naturalized medicinal plants are tested by TLC and Ellman’s colorimetric assay at 250, 125 and 62.5 μg/mL in order to determine the inhibitory effect on AChE. In total, 21 out of 90 extracts show high anti-AChE activity (75–100% inhibition) in a dose-dependent manner. Among them, ethanolic extract from aerial parts of O. vulgare ssp. vulgare shows an IC50 value 7.7 times lower than galantamine. This research also establishes the chemical profile of oregano extract by TLC, HPLC-DAD and LC-MS, and twenty-three compounds are identified and quantified. Dihydroxycinnamic acids and flavonoids are the most abundant ones (56.90 and 25.94%, respectively). Finally, total phenolic compounds and antioxidant properties are quantified by colorimetric methods. The total phenolic content is 207.64 ± 0.69 µg/mg of extract. The antioxidant activity is measured against two radicals, DPPH and ABTS. In both assays, the oregano extract shows high activity. The Pearson correlation matrix shows the relationship between syringic acids, a type of dihydroxybenzoic acid, and anti-AChE (r² = −0.9864) and antioxidant activity (r² = 0.9409 and 0.9976). In conclusion, the results of this study demonstrate promising potential new uses of these medicinal herbs for the treatment of Alzheimer’s. Origanum vulgare ssp. vulgare and syringic acids, which have anti-AChE activity and beneficial antioxidant capacity, can be highlighted as potential candidates for the development of drugs for the treatment of Alzheimer’s disease and other diseases characterized by a cholinergic deficit. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

► Show Figures

Figure 1

17 pages, 2644 KiB

Open AccessArticle

Antiglioma Natural Products from the Marine-Associated Fungus Penicillium sp. ZZ1750

by Kuo Yong, Sidra Kaleem, Mingzhu Ma, Xiaoyuan Lian and Zhizhen Zhang

Molecules 2022, 27(20), 7099; https://doi.org/10.3390/molecules27207099 - 20 Oct 2022

Cited by 9 | Viewed by 2433

Abstract

Marine-derived Penicillium fungi are one of the most important sources for the discovery of new bioactive natural products. This study characterized the isolation, structures, and antiglioma activities of twelve compounds, including three novel ones—penipyridinone B (1), 11S-(−)-penilloid A ( [...] Read more.

Marine-derived Penicillium fungi are one of the most important sources for the discovery of new bioactive natural products. This study characterized the isolation, structures, and antiglioma activities of twelve compounds, including three novel ones—penipyridinone B (1), 11S-(−)-penilloid A (2), and 11R,14E-(+)-penilloid A (3)—from the marine fungus Penicillium sp. ZZ1750. The structures of the novel compounds were determined via extensive nuclear magnetic resonance (NMR) spectroscopic analyses, high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, Mosher’s method, optical rotation (OR) calculations, and electronic circular dichroism (ECD) calculations. Penipyridinone B represents the first example of its structural type and showed potent antiglioma activity, with IC₅₀ values of 2.45 μM for U87MG cells and 11.40 μM for U251 cells. The known compounds of questiomycin A (9) and xanthocillin X (10) also showed antiproliferative activity against both U87MG and U251 cells, with IC₅₀ values of 13.65 μM to 22.56 μM. The antiglioma activity of questiomycin A and xanthocillin X may be related to the promotion of reactive oxygen species (ROS) production, the reduction of mitochondrial membrane potential (MMP), and the enhancement of caspase-3 enzyme activity. Full article

(This article belongs to the Special Issue Natural Products: Extraction, Separation, Structure Elucidation and Biological Activities)

► Show Figures

Graphical abstract

52 pages, 117715 KiB

Open AccessArticle

Methods for Rapid Screening of Biologically Active Compounds Present in Plant-Based Extracts

by Katarzyna Godlewska, Paweł Pacyga, Antoni Szumny, Anna Szymczycha-Madeja, Maja Wełna and Izabela Michalak

Molecules 2022, 27(20), 7094; https://doi.org/10.3390/molecules27207094 - 20 Oct 2022

Cited by 19 | Viewed by 7247

Abstract

In recent years, there has been an increased interest in products of natural origin. The extraction procedure of bioactive compounds from plant matrices is a crucial step in the development of useful new bioproducts for everyday life. The utilisation of analyses enabling the [...] Read more.

In recent years, there has been an increased interest in products of natural origin. The extraction procedure of bioactive compounds from plant matrices is a crucial step in the development of useful new bioproducts for everyday life. The utilisation of analyses enabling the rapid identification of the presence of a given group of compounds can be helpful in the early stages of the development of new products in order to save time and reduce costs. Within this article, we have presented a comparison of different, accessible methods for the identification of various bioactive compounds, e.g., saponins, carboxylic acids, oils and fats, proteins and amino acids, steroids, and alkaloids in plant-based extracts. Additionally, the multielemental composition of extracts was also examined. The applied methods allowed for confirmation of the presence of biologically active compounds in bio-products obtained by ultrasound-assisted extraction. At a later stage, these procedures should be supplemented by advanced analytical techniques in order to determine the plant chemicals’ content qualitatively and quantitatively. Full article

(This article belongs to the Special Issue Extraction, Identification and Isolation of Chemical Compounds in Natural Matrices)

16 pages, 1965 KiB

Open AccessArticle

Bioaccessibility of Betalains in Beetroot (Beta vulgaris L.) Juice under Different High-Pressure Techniques

by Urszula Trych, Magdalena Buniowska-Olejnik and Krystian Marszałek

Molecules 2022, 27(20), 7093; https://doi.org/10.3390/molecules27207093 - 20 Oct 2022

Cited by 14 | Viewed by 3339

Abstract

The influence of high hydrostatic pressure (HHP) and supercritical carbon dioxide (SCCD) on the bioaccessibility of betalains in beetroot (Beta vulgaris L.) juice was investigated. Freshly squeezed juice (FJ) was treated at a mild temperature of 45 °C for 10 min (T45), [...] Read more.

The influence of high hydrostatic pressure (HHP) and supercritical carbon dioxide (SCCD) on the bioaccessibility of betalains in beetroot (Beta vulgaris L.) juice was investigated. Freshly squeezed juice (FJ) was treated at a mild temperature of 45 °C for 10 min (T45), pasteurization at 85 °C for 10 min (T85), HHP at 200, 400, and 500 MPa at 20 °C for 5 min (HHP200, HHP400, HHP500) and SCCD at 10, 30 and 60 MPa at 45 °C for 10 min (SCCD10, SCCD30, SCCD60). The juice was subjected to an in vitro digestion system equipped with dialysis. The content of betalains was measured with the aid of a High-Performance Liquid Chromatography (HPLC), the antioxidant capacity (AC) (ABTS•+, DPPH•) was analyzed during each digestion step, and the bioaccessibility of betacyanins and betaxanthins was assessed. The SCCD at 30 and 60 MPa significantly increased pigments’ bioaccessibility compared with other samples. The 30 MPa proved particularly advantageous, as it increased the bioaccessibility of the total betacyanins and the betaxanthins by 58% and 64%, respectively, compared to the T85 samples. Additionally, higher bioaccessibility of betacyanins was noted in HHP200 and HHP400, by 35% and 32%, respectively, compared to FJ, T45, and T85 samples. AC measured by ABTS•+ and DPPH• assays were not unequivocal. However, both assays showed significantly higher AC in SCCD60 compared to T85 (21% and 31%, respectively). This research contributed to the extended use of the HHP and/or SCCD to design food with higher health-promoting potentials. Full article

(This article belongs to the Special Issue Bioactive Compounds of Fruits, Vegetables and Mushrooms II)

► Show Figures

Graphical abstract

21 pages, 3062 KiB

Open AccessArticle

Acetylcholinesterase Inhibitory Activities of Essential Oils from Vietnamese Traditional Medicinal Plants

by Nguyen Huy Hung, Pham Minh Quan, Prabodh Satyal, Do Ngoc Dai, Vo Van Hoa, Ngo Gia Huy, Le Duc Giang, Nguyen Thi Ha, Le Thi Huong, Vu Thi Hien and William N. Setzer

Molecules 2022, 27(20), 7092; https://doi.org/10.3390/molecules27207092 - 20 Oct 2022

Cited by 51 | Viewed by 4875

Abstract

Essential oils are promising as environmentally friendly and safe sources of pesticides for human use. Furthermore, they are also of interest as aromatherapeutic agents in the treatment of Alzheimer’s disease, and inhibition of the enzyme acetylcholinesterase (AChE) has been evaluated as an important [...] Read more.

Essential oils are promising as environmentally friendly and safe sources of pesticides for human use. Furthermore, they are also of interest as aromatherapeutic agents in the treatment of Alzheimer’s disease, and inhibition of the enzyme acetylcholinesterase (AChE) has been evaluated as an important mechanism. The essential oils of some species in the genera Callicarpa, Premna, Vitex and Karomia of the family Lamiaceae were evaluated for inhibition of electric eel AChE using the Ellman method. The essential oils of Callicarpa candicans showed promising activity, with IC₅₀ values between 45.67 and 58.38 μg/mL. The essential oils of Callicarpa sinuata, Callicarpa petelotii, Callicarpa nudiflora, Callicarpa erioclona and Vitex ajugifolia showed good activity with IC₅₀ values between 28.71 and 54.69 μg/mL. The essential oils Vitex trifolia subsp. trifolia and Callicarpa rubella showed modest activity, with IC₅₀ values of 81.34 and 89.38, respectively. trans-Carveol showed an IC₅₀ value of 102.88 µg/mL. Molecular docking and molecular dynamics simulation were performed on the major components of the studied essential oils to investigate the possible mechanisms of action of potential inhibitors. The results obtained suggest that these essential oils may be used to control mosquito vectors that transmit pathogenic viruses or to support the treatment of Alzheimer’s disease. Full article

(This article belongs to the Special Issue Essential Oils II)

► Show Figures

Figure 1

18 pages, 4517 KiB

Open AccessArticle

Polygonatum cyrtonema Hua Polysaccharides Protect BV2 Microglia Relief Oxidative Stress and Ferroptosis by Regulating NRF2/HO-1 Pathway

by Jiayu Li, Xifan Wang, Rongrong Zhou, Fei Cheng, Xueyang Tang, Jia Lao, Linben Xu, Wei He, Dan Wan, Hongliang Zeng and Shuihan Zhang

Molecules 2022, 27(20), 7088; https://doi.org/10.3390/molecules27207088 - 20 Oct 2022

Cited by 29 | Viewed by 3862

Abstract

Neuronal-regulated cell death (RCD) due to the accumulation of ROS within the central nervous system (CNS) is one of the crucial causes of central system diseases. Caspase-dependent apoptosis is the only form of RCD. As research progressed, several nonapoptotic cell death pathway RCDs [...] Read more.

Neuronal-regulated cell death (RCD) due to the accumulation of ROS within the central nervous system (CNS) is one of the crucial causes of central system diseases. Caspase-dependent apoptosis is the only form of RCD. As research progressed, several nonapoptotic cell death pathway RCDs were identified. Ferroptosis is a nonapoptotic RCD characterized by lipid peroxidation and plasma membrane damage. Polygonatum cyrtonema Hua. Polysaccharides (PCP) are an effective antioxidant. Based on this, the protective effect and mechanism of PCP against H₂O₂-induced microglial injury were investigated. Furthermore, the protective mechanism of PCP against ferroptosis in microglia was explored. Our results indicated that PCP could reduce oxidative stress-induced ROS accumulation by activating the NRF2/HO-1 signaling pathway, thus attenuating RCD in microglia. Subsequent studies have revealed that PCP alleviates ferroptosis in microglia due to protein levels of ERASTIN/RSL3 inhibitor SLC7A11/GPX4 by activating the NRF2/HO-1 signaling pathway. Therefore, we hypothesized that PCP exerts antioxidative and anti-ferroptosis effects by activating the expression of the NRF2/HO-1 pathway. This facilitates new ideas for clinically effective prevention and treatment of diseases due to accumulated reactive oxygen species in the CNS. Simultaneously, PCP has the development potential as a new drug candidate for treating CNS diseases. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

► Show Figures

Figure 1

29 pages, 485 KiB

Open AccessReview

Natural Compounds and Products from an Anti-Aging Perspective

by Geir Bjørklund, Mariia Shanaida, Roman Lysiuk, Monica Butnariu, Massimiliano Peana, Ioan Sarac, Oksana Strus, Kateryna Smetanina and Salvatore Chirumbolo

Molecules 2022, 27(20), 7084; https://doi.org/10.3390/molecules27207084 - 20 Oct 2022

Cited by 117 | Viewed by 21121

Abstract

Aging is a very complex process that is accompanied by a degenerative impairment in many of the major functions of the human body over time. This inevitable process is influenced by hereditary factors, lifestyle, and environmental influences such as xenobiotic pollution, infectious agents, [...] Read more.

Aging is a very complex process that is accompanied by a degenerative impairment in many of the major functions of the human body over time. This inevitable process is influenced by hereditary factors, lifestyle, and environmental influences such as xenobiotic pollution, infectious agents, UV radiation, diet-borne toxins, and so on. Many external and internal signs and symptoms are related with the aging process and senescence, including skin dryness and wrinkles, atherosclerosis, diabetes, neurodegenerative disorders, cancer, etc. Oxidative stress, a consequence of the imbalance between pro- and antioxidants, is one of the main provoking factors causing aging-related damages and concerns, due to the generation of highly reactive byproducts such as reactive oxygen and nitrogen species during the metabolism, which result in cellular damage and apoptosis. Antioxidants can prevent these processes and extend healthy longevity due to the ability to inhibit the formation of free radicals or interrupt their propagation, thereby lowering the level of oxidative stress. This review focuses on supporting the antioxidant system of the organism by balancing the diet through the consumption of the necessary amount of natural ingredients, including vitamins, minerals, polyunsaturated fatty acids (PUFA), essential amino acids, probiotics, plants’ fibers, nutritional supplements, polyphenols, some phytoextracts, and drinking water. Full article

(This article belongs to the Special Issue Exploration of Natural Compounds: Pharmaceutical, Phytochemical and Biological Analysis)

15 pages, 1035 KiB

Open AccessArticle

The Inhibition of α-Glucosidase, α-Amylase and Protein Glycation by Phenolic Extracts of Cotoneaster bullatus, Cotoneaster zabelii, and Cotoneaster integerrimus Leaves and Fruits: Focus on Anti-Hyperglycemic Activity and Kinetic Parameters

by Agnieszka Kicel, Anna Magiera, Marta Skrzywanek, Mariola Malczuk and Monika Anna Olszewska

Molecules 2022, 27(20), 7081; https://doi.org/10.3390/molecules27207081 - 20 Oct 2022

Cited by 14 | Viewed by 4955

Abstract

Cotoneaster species have gained significant importance in traditional Asian medicine for their ability to prevent and treat hyperglycemia and diabetes. Therefore, in this study, some aspects of the beneficial health effects of hydromethanolic extracts of C. bullatus, C. zabelii, and C. integerrimus [...] Read more.

Cotoneaster species have gained significant importance in traditional Asian medicine for their ability to prevent and treat hyperglycemia and diabetes. Therefore, in this study, some aspects of the beneficial health effects of hydromethanolic extracts of C. bullatus, C. zabelii, and C. integerrimus leaves and fruits were evaluated, including their influence on α-glucosidase, α-amylase, and nonenzymatic protein glycation. The activity was investigated in relation to the polyphenolic profile of the extracts determined by UV-spectrophotometric and HPLC-PDA-fingerprint methods. It was revealed that all leaf and fruit extracts are a promising source of biological components (caffeic acid pseudodepsides, proanthocyanidins, and flavonols), and the leaf extracts of C. bullatus and C. zabelii contain the highest levels of polyphenols (316.3 and 337.6 mg/g in total, respectively). The leaf extracts were also the most effective inhibitors of digestive enzymes and nonenzymatic protein glycation. IC₅₀ values of 8.6, 41.8, and 32.6 µg/mL were obtained for the most active leaf extract of C. bullatus (MBL) in the α-glucosidase, α-amylase, and glycation inhibition tests, respectively. In the kinetic study, MBL was displayed as a mixed-type inhibitor of both enzymes. The correlations between the polyphenol profiles and activity parameters (|r| > 0.72, p < 0.05) indicate a significant contribution of proanthocyanidins to the tested activity. These results support the traditional use of Cotoneaster leaves and fruits in diabetes and suggest their hydrophilic extracts be promising in functional applications. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

► Show Figures

Graphical abstract

24 pages, 2547 KiB

Open AccessReview

Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives

by Jagjit Singh Dhaliwal, Said Moshawih, Khang Wen Goh, Mei Jun Loy, Md. Sanower Hossain, Andi Hermansyah, Vijay Kotra, Nurolaini Kifli, Hui Poh Goh, Sachinjeet Kaur Sodhi Dhaliwal, Hayati Yassin and Long Chiau Ming

Molecules 2022, 27(20), 7062; https://doi.org/10.3390/molecules27207062 - 19 Oct 2022

Cited by 77 | Viewed by 9399

Abstract

Chalcones have been well examined in the extant literature and demonstrated antibacterial, antifungal, anti-inflammatory, and anticancer properties. A detailed evaluation of the purported health benefits of chalcone and its derivatives, including molecular mechanisms of pharmacological activities, can be further explored. Therefore, this review [...] Read more.

Chalcones have been well examined in the extant literature and demonstrated antibacterial, antifungal, anti-inflammatory, and anticancer properties. A detailed evaluation of the purported health benefits of chalcone and its derivatives, including molecular mechanisms of pharmacological activities, can be further explored. Therefore, this review aimed to describe the main characteristics of chalcone and its derivatives, including their method synthesis and pharmacotherapeutics applications with molecular mechanisms. The presence of the reactive α,β-unsaturated system in the chalcone’s rings showed different potential pharmacological properties, including inhibitory activity on enzymes, anticancer, anti-inflammatory, antibacterial, antifungal, antimalarial, antiprotozoal, and anti-filarial activity. Changing the structure by adding substituent groups to the aromatic ring can increase potency, reduce toxicity, and broaden pharmacological action. This report also summarized the potential health benefits of chalcone derivatives, particularly antimicrobial activity. We found that several chalcone compounds can inhibit diverse targets of antibiotic-resistance development pathways; therefore, they overcome resistance, and bacteria become susceptible to antibacterial compounds. A few chalcone compounds were more active than conventional antibiotics, like vancomycin and tetracycline. On another note, a series of pyran-fused chalcones and trichalcones can block the NF-B signaling complement system implicated in inflammation, and several compounds demonstrated more potent lipoxygenase inhibition than NSAIDs, such as indomethacin. This report integrated discussion from the domains of medicinal chemistry, organic synthesis, and diverse pharmacological applications, particularly for the development of new anti-infective agents that could be a useful reference for pharmaceutical scientists. Full article

(This article belongs to the Special Issue Flavonoids’ and Other Polyphenols’ Pharmacological Activities for Phytopharmaceutical and Medicinal Applications)

► Show Figures

Figure 1

17 pages, 3587 KiB

Open AccessArticle

Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method

by Jing Li, Qiao Qin, Sheng-Hua Zha, Qing-Sheng Zhao, Hang Li, Lu-Peng Liu, Shou-Bu Hou and Bing Zhao

Molecules 2022, 27(20), 7055; https://doi.org/10.3390/molecules27207055 - 19 Oct 2022

Cited by 12 | Viewed by 2652

Abstract

In this study, a green process of β-cyclodextrin (β-CD)-assisted extraction of active ingredients from Forsythia suspensa leaves was developed. Firstly, the optimal process of extraction was as follows: the ratio between Forsythia suspensa leaves and β-CD was 3.61:5, the solid–liquid ratio was 1:36.3, [...] Read more.

In this study, a green process of β-cyclodextrin (β-CD)-assisted extraction of active ingredients from Forsythia suspensa leaves was developed. Firstly, the optimal process of extraction was as follows: the ratio between Forsythia suspensa leaves and β-CD was 3.61:5, the solid–liquid ratio was 1:36.3, the temperature was 75.25 °C and the pH was 3.94. The yields of forsythoside A, phillyrin and phillygenol were 11.80 ± 0.141%, 5.49 ± 0.078% and 0.319 ± 0.004%, respectively. Then, the structure characteristics of the β-CD-assisted extract of Forsythia suspensa leaves (FSE-β-CD) were analyzed using powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), scanning electron microscopy (SEM) and molecular docking to demonstrate that the natural active products from Forsythia suspensa leaves had significant interactions with the β-CD. Additionally, the loss of forsythoside A from aqueous FSE-CD at 80 °C was only 12%, compared with Forsythia suspensa leaf extract (FSE) which decreased by 13%. In addition, the aqueous solubility of FSE-CD was significantly increased to 70.2 g/L. The EC₅₀ for scavenging DPPH and ABTS radicals decreased to 28.98 ug/mL and 25.54 ug/mL, respectively. The results showed that the β-CD-assisted extraction process would be a promising technology for bioactive compounds extracted from plants. Full article

(This article belongs to the Special Issue The Role of Natural Products in Promoting Well-being: From Foods to Drugs)

► Show Figures

Figure 1

10 pages, 1059 KiB

Open AccessArticle

Cinnamomum verum J. Presl Bark Contains High Contents of Nicotinamide Mononucleotide

by Jing Yan, Takumi Sakamoto, Ariful Islam, Yashuang Ping, Soho Oyama, Hiroyuki Fuchino, Hitomi Kawakami, Kayo Yoshimatsu, Tomoaki Kahyo and Mitsutoshi Setou

Molecules 2022, 27(20), 7054; https://doi.org/10.3390/molecules27207054 - 19 Oct 2022

Cited by 5 | Viewed by 3732

Abstract

The global population is aging, and intervention strategies for anti-aging and the prevention of aging-related diseases have become a topic actively explored today. Nicotinamide adenine dinucleotide (NAD⁺) is an important molecule in the metabolic process, and its content in tissues and [...] Read more.

The global population is aging, and intervention strategies for anti-aging and the prevention of aging-related diseases have become a topic actively explored today. Nicotinamide adenine dinucleotide (NAD⁺) is an important molecule in the metabolic process, and its content in tissues and cells decreases with age. The supplementation of nicotinamide mononucleotide (NMN), an important intermediate and precursor of NAD⁺, has increased NAD⁺ levels, and its safety has been demonstrated in rodents and human studies. However, the high content of NMN in natural plants has not been fully explored as herbal medicines for drug development. Here, we identified that the leaf of Cinnamomum verum J. Presl (C. verum) was the highest NMN content among the Plant Extract Library (PEL) with food experience, using ultra-performance liquid chromatography–tandem mass spectrometry (UPLC-MS/MS). To validate this result, the extraction and quantitative analysis of bark, leaf, root, and stem of fresh C. verum was conducted. The results revealed that the bark had the highest NMN content in C. verum (0.471 mg/100 g). Our study shed light on the prospects of developing natural plants in the context of NMN as drugs for anti-aging and prevention of aging-related diseases. The future should focus on the development and application of C. verum pharmaceutical formulations. Full article

(This article belongs to the Special Issue Discovery of Bioactive Ingredients from Natural Products, 3rd Edition)

► Show Figures

Figure 1

12 pages, 2481 KiB

Open AccessArticle

Bioassay-Guided Isolation of Iridoid Glucosides from Stenaria nigricans, Their Biting Deterrence against Aedes aegypti (Diptera: Culicidae), and Repellency Assessment against Imported Fire Ants (Hymenoptera: Formicidae)

by Fazila Zulfiqar, Abbas Ali, Zulfiqar Ali and Ikhlas A. Khan

Molecules 2022, 27(20), 7053; https://doi.org/10.3390/molecules27207053 - 19 Oct 2022

Cited by 2 | Viewed by 1875

Abstract

In our natural product screening program, we screened natural products for their repellency and toxicity against insect vectors. Methanolic extract of aerial parts of Stenaria nigricans (Lam.), with no published chemistry, was tested for repellency against mosquitoes and imported hybrid fire ants. Methanolic [...] Read more.

In our natural product screening program, we screened natural products for their repellency and toxicity against insect vectors. Methanolic extract of aerial parts of Stenaria nigricans (Lam.), with no published chemistry, was tested for repellency against mosquitoes and imported hybrid fire ants. Methanolic extracts showed biting deterrence similar to DEET (N,N-diethyl-3-methylbenzamide) against Aedes aegypti L. Based on this activity, the crude extract was fractionated into chloroform, ethyl acetate, and methanol subfractions. The active methanolic subfraction was further fractionated into 13 subfractions. These fractions were tested for their biting deterrence against Ae. Aegypti. Active subfractions were further characterized to identify the compounds responsible for this activity. Four undescribed iridoid glucosides (1–4) and three previously reported compounds (5–7) were isolated from active subfractions and tested for their biting deterrent activity. Based on BDI values, compounds 2, 3, 6, and 7, with biting deterrence similar to DEET, showed the potential to be used as repellents against mosquitoes. In an in vitro digging bioassay, none of these compounds showed any repellency against hybrid imported fire ants at a dose of 125 µg/g. This is the first report of biting deterrence and repellency of S. nigricans extract and its pure compounds, iridoid glucosides against mosquitoes and imported fire ants. Further studies will be conducted to explore the repellent potential of these compounds in different formulations under field conditions. Full article

(This article belongs to the Special Issue Exclusive Feature Papers in Natural Products Chemistry)

► Show Figures

Graphical abstract

20 pages, 4113 KiB

Open AccessReview

Important Hormones Regulating Lipid Metabolism

by Dengke Zhang, Yanghui Wei, Qingnan Huang, Yong Chen, Kai Zeng, Weiqin Yang, Juan Chen and Jiawei Chen

Molecules 2022, 27(20), 7052; https://doi.org/10.3390/molecules27207052 - 19 Oct 2022

Cited by 66 | Viewed by 17231

Abstract

There is a wide variety of kinds of lipids, and complex structures which determine the diversity and complexity of their functions. With the basic characteristic of water insolubility, lipid molecules are independent of the genetic information composed by genes to proteins, which determine [...] Read more.

There is a wide variety of kinds of lipids, and complex structures which determine the diversity and complexity of their functions. With the basic characteristic of water insolubility, lipid molecules are independent of the genetic information composed by genes to proteins, which determine the particularity of lipids in the human body, with water as the basic environment and genes to proteins as the genetic system. In this review, we have summarized the current landscape on hormone regulation of lipid metabolism. After the well-studied PI3K-AKT pathway, insulin affects fat synthesis by controlling the activity and production of various transcription factors. New mechanisms of thyroid hormone regulation are discussed, receptor α and β may mediate different procedures, the effect of thyroid hormone on mitochondria provides a new insight for hormones regulating lipid metabolism. Physiological concentration of adrenaline induces the expression of extrapituitary prolactin in adipose tissue macrophages, which promotes fat weight loss. Manipulation of hormonal action has the potential to offer a new therapeutic horizon for the global burden of obesity and its associated complications such as morbidity and mortality. Full article

(This article belongs to the Special Issue Natural Molecules Controlling Lipid Metabolism)

► Show Figures

Figure 1

19 pages, 1600 KiB

Open AccessArticle

Comparison of the Effect of Cold Plasma with Conventional Preservation Methods on Red Wine Quality Using Chemometrics Analysis

by Iwona Niedźwiedź, Vasil Simeonov, Adam Waśko and Magdalena Polak-Berecka

Molecules 2022, 27(20), 7048; https://doi.org/10.3390/molecules27207048 - 19 Oct 2022

Cited by 4 | Viewed by 1890

Abstract

In this study, the effect of cold plasma (CP) on the physicochemical and biological properties of red wine was investigated in comparison with the effects of the conventional preservation method and the combined method. In addition, the effect of storage time after the [...] Read more.

In this study, the effect of cold plasma (CP) on the physicochemical and biological properties of red wine was investigated in comparison with the effects of the conventional preservation method and the combined method. In addition, the effect of storage time after the application of each of the analyzed methods was evaluated. The study examined the effects of the different preservation methods on the pH, color, phenolic content, antioxidant activity and microbiological purity of the red wine. Chemometric analysis was used to discover the relationship between the preservation method used and wine quality. In the wine samples tested, a reduction in phenolic compounds and a decrease in antioxidant activity were noted after storage. This effect was mildest for preservation methods with the addition of potassium metabisulphite and those in which a mixture of helium and nitrogen was used as the working gas. On a positive note, the CP treatment did not affect the color of the wine in a way perceptible to the consumer: ∆E*—1.12 (He/N₂; 5 min). In addition, the lowest growth of microorganisms was detected in the CP-treated samples. This indicates the potential of cold plasma as an alternative method to the use of potassium metabisulfite in wine production, which may contribute to its wider use in the alcohol industry in the future. Full article

(This article belongs to the Special Issue Bioactive Ingredients in Foods: A Challenging Journey to Bioefficacy)

► Show Figures

Figure 1

12 pages, 1235 KiB

Open AccessArticle

Anti-HIV Ermiasolides from Croton megalocarpus

by Ermias Mergia Terefe, Faith Apolot Okalebo, Solomon Derese, Moses K. Langat, Eduard Mas-Claret, Kamal Ahmad Qureshi, Mariusz Jaremko and Joseph Muriuki

Molecules 2022, 27(20), 7040; https://doi.org/10.3390/molecules27207040 - 19 Oct 2022

Cited by 12 | Viewed by 2705

Abstract

In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy [...] Read more.

In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy eudesm-7(11)-en-12,8-olide (2) and 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3). These are trivially named ermiasolide A-C and were isolated from the bark of Croton megalocarpus. 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), showed the highest anti-HIV activity by inhibiting 93% of the viral replication with an IC₅₀ = 0.002 µg/mL. On the other hand, 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3) and 5β,8α-dihydroxy eudesm-7(11)-en-12,8-olide (2), inhibited viral replication by 77.5% at IC₅₀ = 0.04 µg/mL and 69.5% at IC₅₀ = 0.002 µg/mL, respectively. Molecular docking studies showed that the proposed mechanism of action leading to these results is through the inhibition of HIV-protease. Full article

(This article belongs to the Section Natural Products Chemistry)

► Show Figures

Figure 1

22 pages, 1563 KiB

Open AccessReview

Potential of Essential Oil-Based Anticholinesterase Insecticides against Anopheles Vectors: A Review

by Thankhoe A. Rants’o, Lizette L. Koekemoer, Jenny-Lee Panayides and Robyn L. van Zyl

Molecules 2022, 27(20), 7026; https://doi.org/10.3390/molecules27207026 - 18 Oct 2022

Cited by 18 | Viewed by 3747

Abstract

The insect nervous system is critical for its functional integrity. The cholinergic system, of which acetylcholinesterase (AChE) is a key enzyme, is essential to the Anopheles (consisting of major malaria vector species) nervous system. Furthermore, the nervous system is also the primary target [...] Read more.

The insect nervous system is critical for its functional integrity. The cholinergic system, of which acetylcholinesterase (AChE) is a key enzyme, is essential to the Anopheles (consisting of major malaria vector species) nervous system. Furthermore, the nervous system is also the primary target site for insecticides used in malaria vector control programs. Insecticides, incorporated in insecticide-treated nets and used for indoor residual spraying, are a core intervention employed in malaria vector control. However, Anopheles resistance against these insecticides has grown rapidly. Due to this major setback, novel agents with potential activity against resistant Anopheles and/or capacity to overcome resistance against current WHO-approved insecticides are urgently needed. The essential oils have the potential to be natural sources of novel insecticides with potential to inhibit the Anopheles AChE target. In the current review, the scientific evidence highlights the ability of essential oils and specific essential oil constituents to serve as anticholinesterase insecticides. For this reason, the published data from scientific databases on the essential oils and essential oil constituents on anticholinesterase, ovicidal, larvicidal, pupicidal and adulticidal activities were analyzed. The identification of major constituents in active essential oils and their possible influence on the biological activity have also been critically evaluated. Furthermore, the toxicity to mammals as well as potential activity against the mammalian AChE target has also been reviewed. The importance of identifying novel potent insecticides from essential oils has been discussed, in relation to human safety and cost-effectiveness. Finally, the critical insights from this review can be used to inform future researchers towards potent and safe anticholinesterase insecticides for the management of Anopheles malaria vectors. Full article

(This article belongs to the Special Issue Essential Oils: Characterization, Biological Activity and Application)

► Show Figures

Figure 1

18 pages, 5740 KiB

Open AccessArticle

Does the Metabolome of Wild-like Dendrobium officinale of Different Origins Have Regional Differences?

by Qiqian Lan, Chenxing Liu, Zhanghua Wu, Chen Ni, Jinyan Li, Chunlei Huang, Huan Wang and Gang Wei

Molecules 2022, 27(20), 7024; https://doi.org/10.3390/molecules27207024 - 18 Oct 2022

Cited by 13 | Viewed by 2439

Abstract

Dendrobium officinale, as a traditional Chinese medicine, has considerable commercial value and pharmacological activity. Environmental factors of different origins have a great influence on Dendrobium officinale metabolites, which affect its pharmacological activity. This study sought to identify the differential metabolites of wild-imitating [...] Read more.

Dendrobium officinale, as a traditional Chinese medicine, has considerable commercial value and pharmacological activity. Environmental factors of different origins have a great influence on Dendrobium officinale metabolites, which affect its pharmacological activity. This study sought to identify the differential metabolites of wild-imitating cultivated D. officinale stems of different origins. Using the widely-targeted metabolomics approach, 442 metabolites were detected and characterized, including flavonoids, lipids, amino acids and derivatives, and alkaloids. We found that although the chemical constitution of D. officinale cultured in the three habitats was parallel, the contents were significantly different. Meanwhile, the KEGG pathway enrichment analysis revealed that the distinctive metabolites among the three groups were mainly involved in flavone and flavonol biosynthesis. To further explore the different contents of flavonoids, HPLC was performed on four main flavonoid contents, which can be used as one of the references to distinguish D. officinale from different growing origins. In conclusion, a comprehensive profile of the metabolic differences of D. officinale grown in different origins was provided, which contributed a scientific basis for further research on the quality evaluation of D. officinale. Full article

(This article belongs to the Special Issue Analysis of Plant Metabolites, Antioxidants Compound and Enzymes Activity in Plants)

► Show Figures

Graphical abstract

27 pages, 12614 KiB

Open AccessArticle

The Potential of Corchorus olitorius Seeds Buccal Films for Treatment of Recurrent Minor Aphthous Ulcerations in Human Volunteers

by Nourhan Hisham Shady, Abdullah H. Altemani, Faisal H. Altemani, Sherif A. Maher, Mahmoud A. Elrehany, Entesar Ali Saber, Ahmed M. Badawi, Fatma Mohamed Abd El-Mordy, Nada M. Mohamed, Mohammed A. S. Abourehab, Ahmed M. Sayed, Usama Ramadan Abdelmohsen and Soad A. Mohamad

Molecules 2022, 27(20), 7020; https://doi.org/10.3390/molecules27207020 - 18 Oct 2022

Cited by 12 | Viewed by 3451

Abstract

Aphthous ulcers are very common disorders among different age groups and are very noxious and painful. The incidence of aphthous ulcer recurrence is very high and it may even last for a maximum of 6 days and usually, patients cannot stand its pain. [...] Read more.

Aphthous ulcers are very common disorders among different age groups and are very noxious and painful. The incidence of aphthous ulcer recurrence is very high and it may even last for a maximum of 6 days and usually, patients cannot stand its pain. This study aims to prepare a buccoadhesive fast dissolving film containing Corchorus olitorius seed extract to treat recurrent minor aphthous ulceration (RMAU) in addition to clinical experiments on human volunteers. An excision wound model was used to assess the in vivo wound healing potential of Corchorus olitorius L. seed extract, with a focus on wound healing molecular targets such as TGF-, TNF-, and IL-1. In addition, metabolomic profiling using HR-LCMS for the crude extract of Corchorus olitorius seeds was explored. Moreover, molecular docking experiments were performed to elucidate the binding confirmation of the isolated compounds with three molecular targets (TNF-α, IL-1β, and GSK3). Additionally, the in vitro antioxidant potential of C. olitorius seed extract using both H₂O₂ and superoxide radical scavenging activity was examined. Clinical experiments on human volunteers revealed the efficiency of the prepared C. olitorius seeds buccal fast dissolving film (CoBFDF) in relieving pain and wound healing of RMAU. Moreover, the wound healing results revealed that C. olitorius seed extract enhanced wound closure rates (p ≤ 0.001), elevated TGF-β levels and significantly downregulated TNF-α and IL-1β in comparison to the Mebo-treated group. The phenotypical results were supported by biochemical and histopathological findings, while metabolomic profiling using HR-LCMS for the crude extract of Corchorus olitorius seeds yielded a total of 21 compounds belonging to diverse chemical classes. Finally, this study highlights the potential of C. olitorius seed extract in wound repair uncovering the most probable mechanisms of action using in silico analysis. Full article

(This article belongs to the Special Issue Novel Natural Compounds as Wound Healing Agents)

► Show Figures

Figure 1

15 pages, 1756 KiB

Open AccessArticle

Ultrasound, Acetic Acid, and Peracetic Acid as Alternatives Sanitizers to Chlorine Compounds for Fresh-Cut Kale Decontamination

by Maria Clara de Moraes Motta Machado, Bárbara Morandi Lepaus, Patrícia Campos Bernardes and Jackline Freitas Brilhante de São José

Molecules 2022, 27(20), 7019; https://doi.org/10.3390/molecules27207019 - 18 Oct 2022

Cited by 6 | Viewed by 2741

Abstract

Chlorinated compounds are usually applied in vegetable sanitization, but there are concerns about their application. Thus, this study aimed to evaluate ultrasound (50 kHz), acetic acid (1000; 2000 mg/L), and peracetic acid (20 mg/L) and their combination as alternative treatments to 200 mg/L [...] Read more.

Chlorinated compounds are usually applied in vegetable sanitization, but there are concerns about their application. Thus, this study aimed to evaluate ultrasound (50 kHz), acetic acid (1000; 2000 mg/L), and peracetic acid (20 mg/L) and their combination as alternative treatments to 200 mg/L sodium dichloroisocyanurate. The overall microbial, physicochemical, and nutritional quality of kale stored at 7 °C were assessed. The impact on Salmonella enterica Typhimurium was verified by plate-counting and scanning electron microscopy. Ultrasound combined with peracetic acid exhibited higher reductions in aerobic mesophiles, molds and yeasts, and coliforms at 35 °C (2.6; 2.4; 2.6 log CFU/g, respectively). Microbial counts remained stable during storage. The highest reduction in Salmonella occurred with the combination of ultrasound and acetic acid at 1000 mg/L and acetic acid at 2000 mg/L (2.8; 3.8 log CFU/g, respectively). No synergistic effect was observed with the combination of treatments. The cellular morphology of the pathogen altered after combinations of ultrasound and acetic acid at 2000 mg/L and peracetic acid. No changes in titratable total acidity, mass loss, vitamin C, or total phenolic compounds occurred. Alternative treatments presented equal to or greater efficacies than chlorinated compounds, so they could potentially be used for the decontamination of kale. Full article

(This article belongs to the Special Issue Food Processing and Its Impact on Phenolic and Other Bioactive Constituents in Food – Second Edition)

► Show Figures

Figure 1

14 pages, 527 KiB

Open AccessArticle

Qualitative Analysis Related to Palynological Characterization and Biological Evaluation of Propolis from Prespa National Park (Greece)

by Elisavet Pyrgioti, Konstantia Graikou, Nektarios Aligiannis, Sofia Karabournioti and Ioanna Chinou

Molecules 2022, 27(20), 7018; https://doi.org/10.3390/molecules27207018 - 18 Oct 2022

Cited by 10 | Viewed by 2228

Abstract

Propolis samples from a geographical part of northwest Greece (Prespa National Park, PNP), which is characterized as a plant endemism center and biodiversity hotspot, were characterized through pollen analysis, chemically analyzed, and biologically evaluated. The majority of the studied propolis showed typical chemical [...] Read more.

Propolis samples from a geographical part of northwest Greece (Prespa National Park, PNP), which is characterized as a plant endemism center and biodiversity hotspot, were characterized through pollen analysis, chemically analyzed, and biologically evaluated. The majority of the studied propolis showed typical chemical constituents (phenolic acids, flavonoids, and chalcones) of European type, while a sample of Mediterranean-type propolis (rich in diterpenes) was also identified. The palynological characterization was implemented to determine the botanical origin and to explain the chemical composition. The total phenolic content and the DPPH assay showed that the European-type propolis samples possessed strong antioxidant activity (86–91% inhibition at 200 μg/mL). Moreover, promising antibacterial activity of the extracts (MIC values 0.56–1.95 mg/mL) and moderate antifungal activity (MIC values 1.13–2.40 mg/mL) were noticed, while the sample with the highest activity had a significant content in terpenes (Mediterranean type). Propolis samples from the PNP area represent a rich source of antibacterial and antioxidant compounds and confirm the fact that propolis is a significant natural product with potential use for improving human health and stimulating the body’s defense. Finally, it is noteworthy that a significant chemical diversity was demonstrated, even in samples from a limited geographical area as this of PNP. Full article

(This article belongs to the Special Issue Propolis in Human and Bee Health)

► Show Figures

Figure 1

20 pages, 2177 KiB

Open AccessArticle

Metabolomic Analysis of Phytochemical Compounds from Agricultural Residues of Eggplant (Solanum melongena L.)

by Laura Aracely Contreras-Angulo, Aldo Moreno-Ulloa, Rommel A. Carballo-Castañeda, Josefina León-Felix, José Geovanni Romero-Quintana, Maribel Aguilar-Medina, Rosalío Ramos-Payán and J. Basilio Heredia

Molecules 2022, 27(20), 7013; https://doi.org/10.3390/molecules27207013 - 18 Oct 2022

Cited by 19 | Viewed by 5442

Abstract

The eggplant is a fruit rich in natural products and produced worldwide. However, its cultivation generates a large amount of scarcely used agricultural residues with poor chemical characterization. This study aimed to identify and quantify the metabolome and determine the composition of select [...] Read more.

The eggplant is a fruit rich in natural products and produced worldwide. However, its cultivation generates a large amount of scarcely used agricultural residues with poor chemical characterization. This study aimed to identify and quantify the metabolome and determine the composition of select phytochemicals and the overall antioxidant capacity of various anatomical parts of the plant. The plant’s root, leaf, stem, and fruit were analyzed by quantitative mass spectrometry-based untargeted metabolomics and chemoinformatics, and phytochemicals were quantified by spectrophotometric analysis. Moreover, we determined the total antioxidant capacity of the distinct plant parts to infer a possible biological effect of the plant’s metabolites. Various secondary metabolites were identified as terpenes, phenolic compounds, alkaloids, and saponins, distributed throughout the plant. The leaf and fruit presented the highest concentration of phenolic compounds, flavonoids, anthocyanins, and alkaloids, accompanied by the highest antioxidant capacity. Although the stem and root showed the lowest abundance of secondary metabolites, they provided around 20% of such compounds compared with the leaf and fruit. Overall, our study improved the understanding of the eggplant metabolome and concluded that the plant is rich in secondary metabolites, some with antioxidant properties, and shows potential nutraceutical and biopharmaceutical applications. Full article

(This article belongs to the Special Issue Chemical, Nutraceutical Composition and Potential Bio Pharmacological Properties of the Medicinal Plants)

► Show Figures

Figure 1

Journal Menu

Journal Browser

Molecules, Volume 27, Issue 20 (October-2 2022) – 368 articles

Further Information

Guidelines

MDPI Initiatives

Follow MDPI