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29 pages, 7469 KiB

Open AccessArticle

Histochemical and Phytochemical Analysis of Lamium album subsp. album L. Corolla: Essential Oil, Triterpenes, and Iridoids

by Agata Konarska, Elżbieta Weryszko-Chmielewska, Anna Matysik-Woźniak, Aneta Sulborska, Beata Polak, Marta Dmitruk, Krystyna Piotrowska-Weryszko, Beata Stefańczyk and Robert Rejdak

Molecules 2021, 26(14), 4166; https://doi.org/10.3390/molecules26144166 - 8 Jul 2021

Cited by 13 | Viewed by 5703

Abstract

The aim of this study was to conduct a histochemical analysis to localize lipids, terpenes, essential oil, and iridoids in the trichomes of the L. album subsp. album corolla. Morphometric examinations of individual trichome types were performed. Light and scanning electron microscopy techniques [...] Read more.

The aim of this study was to conduct a histochemical analysis to localize lipids, terpenes, essential oil, and iridoids in the trichomes of the L. album subsp. album corolla. Morphometric examinations of individual trichome types were performed. Light and scanning electron microscopy techniques were used to show the micromorphology and localization of lipophilic compounds and iridoids in secretory trichomes with the use of histochemical tests. Additionally, the content of essential oil and its components were determined using gas chromatography-mass spectrometry (GC-MS). Qualitative analyses of triterpenes carried out using high-performance thin-layer chromatography (HPTLC) coupled with densitometric detection, and the iridoid content expressed as aucubin was examined with spectrophotometric techniques. We showed the presence of iridoids and different lipophilic compounds in papillae and glandular and non-glandular trichomes. On average, the flowers of L. album subsp. album yielded 0.04 mL/kg of essential oil, which was dominated by aldehydes, sesquiterpenes, and alkanes. The extract of the L. album subsp. album corolla contained 1.5 × 10^?3 ± 4.3 × 10^?4 mg/mL of iridoid aucubin and three triterpenes: oleanolic acid, ?-amyrin, and ?-amyrin acetate. Aucubin and ?-amyrin acetate were detected for the first time. We suggest the use of L. album subsp. album flowers as supplements in human nutrition. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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16 pages, 1630 KiB

Open AccessArticle

Phytochemical Constituents, Antioxidant Activity, and Toxicity Assessment of the Aerial Part Extracts from the Infraspecific Taxa of Matthiola fruticulosa (Brassicaceae) Endemic to Sicily

by Maria Fernanda Taviano, Emilia Cavò, Vivienne Spadaro, Francesco Maria Raimondo, Vincenzo Musolino, Francesco Cacciola, Yassine Oulad El Majdoub, Luigi Mondello, Concetta Condurso, Fabrizio Cincotta, Antonella Verzera and Natalizia Miceli

Molecules 2021, 26(14), 4114; https://doi.org/10.3390/molecules26144114 - 6 Jul 2021

Cited by 9 | Viewed by 2846

Abstract

In a project designed to investigate the specific and infraspecific taxa of Matthiola endemic to Sicily (Italy) as new potential sources of bioactive compounds in this work, the infraspecific taxa of Matthiola fruticulosa were studied, namely, subsp. fruticulosa and subsp. coronopifolia. HPLC–PDA/ESI–MS [...] Read more.

In a project designed to investigate the specific and infraspecific taxa of Matthiola endemic to Sicily (Italy) as new potential sources of bioactive compounds in this work, the infraspecific taxa of Matthiola fruticulosa were studied, namely, subsp. fruticulosa and subsp. coronopifolia. HPLC–PDA/ESI–MS and SPME–GC/MS analyses of hydroalcoholic extracts obtained from the aerial parts of the two subspecies led to the detection of 51 phenolics and 61 volatile components, highlighting a quite different qualitative–quantitative profile. The antioxidant properties of the extracts were explored through in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), reducing power and Fe²⁺ chelating activity assays. The results of the antioxidant tests showed that the extracts possess a different antioxidant ability: particularly, the extract of M. fruticulosa subsp. fruticulosa exhibited higher radical scavenging activity than that of subsp. coronopifolia (IC₅₀ = 1.25 ± 0.02 mg/mL and 2.86 ± 0.05 mg/mL), which in turn displayed better chelating properties (IC₅₀ = 1.49 ± 0.01 mg/mL and 0.63 ± 0.01 mg/mL). Lastly, Artemia salina lethality bioassay was performed for toxicity assessment. The results of the bioassay showed lack of toxicity against brine shrimp larvae for both extracts. The data presented indicate the infraspecific taxa of M. fruticulosa as new and safe sources of antioxidant compounds. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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20 pages, 4517 KiB

Open AccessArticle

Bioefficacy of Epaltes divaricata (L.) n-Hexane Extracts and Their Major Metabolites against the Lepidopteran Pests Spodoptera litura (fab.) and Dengue Mosquito Aedes aegypti (Linn.)

by Kesavan Amala, Sengodan Karthi, Raja Ganesan, Narayanaswamy Radhakrishnan, Kumaraswamy Srinivasan, Abd El-Zaher M. A. Mostafa, Abdullah Ahmed Al-Ghamdi, Jawaher Alkahtani, Mohamed Soliman Elshikh, Sengottayan Senthil-Nathan, Prabhakaran Vasantha-Srinivasan and Patcharin Krutmuang

Molecules 2021, 26(12), 3695; https://doi.org/10.3390/molecules26123695 - 17 Jun 2021

Cited by 31 | Viewed by 3821

Abstract

The present research investigated the chemical characterization and insecticidal activity of n-Hexane extracts of Epaltes divaricata (NH-EDx) along with their chief derivatives n-Hexadecanoic acid (n-HDa) and n-Octadecanoic acid (n-ODa) against the dengue vector Aedes aegypti and [...] Read more.

The present research investigated the chemical characterization and insecticidal activity of n-Hexane extracts of Epaltes divaricata (NH-EDx) along with their chief derivatives n-Hexadecanoic acid (n-HDa) and n-Octadecanoic acid (n-ODa) against the dengue vector Aedes aegypti and lepidopteran pest Spodoptera litura. Chemical screening of NH-EDx through GC–MS analysis delivered nine major derivatives, and the maximum peak area percentage was observed in n-Hexadecanoic acid (14.63%) followed by n-Octadecadienoic acid (6.73%). The larvicidal activity of NH-EDx (1000 ppm), n-HDa (5 ppm), and n-ODa (5 ppm) against the A. aegypti and S. litura larvae showed significant mortality rate in a dose-dependent way across all the instars. The larvicidal activity was profound in the A. aegypti as compared to the S. litura across all the larval instars. The sublethal dosages of NH-EDx (500 ppm), n-HDa (2.5 ppm), and n-ODa (2.5 ppm) also showed alterations in the larval/pupal durations and adult longevity in both the insect pests. The enzyme activity revealed that the ?- and ?-carboxylesterase levels were decreased significantly in both the insect pests, whereas the levels of GST and CYP450 uplifted in a dose-dependent manner of NH-EDx, n-HDa, and n-ODa. Correspondingly, midgut tissues such as the epithelial layer (EL), gut lumen (GL), peritrophic matrix (Pm), and brush border membrane (BBM) were significantly altered in their morphology across both A. aegypti and S. litura against the NH-EDx and their bioactive metabolites. NH-EDx and their bioactive metabolites n-HDa and n-ODa showed significant larvicidal, growth retardant, enzyme inhibition, and midgut toxicity effects against two crucial agriculturally and medically challenging insect pest of ecological importance. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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11 pages, 1194 KiB

Open AccessArticle

Quercetin and Rutin as Modifiers of Aphid Probing Behavior

by Katarzyna Stec, Bożena Kordan and Beata Gabryś

Molecules 2021, 26(12), 3622; https://doi.org/10.3390/molecules26123622 - 13 Jun 2021

Cited by 17 | Viewed by 3112

Abstract

Rutin and its aglycone quercetin occur in the fruits, leaves, seeds, and grains of many plant species and are involved in plant herbivore interactions. We studied the effect of the exogenous application of rutin and quercetin on the probing behavior (= stylet penetration [...] Read more.

Rutin and its aglycone quercetin occur in the fruits, leaves, seeds, and grains of many plant species and are involved in plant herbivore interactions. We studied the effect of the exogenous application of rutin and quercetin on the probing behavior (= stylet penetration activities in plant tissues) of Acyrthosiphon pisum on Pisum sativum, Myzus persicae on Brassica rapa ssp. pekinensis, and Rhopalosiphum padi on Avena sativa using the electrical penetration graph technique (EPG = electropenetrography). The reaction of aphids to quercetin and rutin and the potency of the effect depended on aphid species, the flavonol, and flavonol concentration. Quercetin promoted probing activities of A. pisum within non-phloem and phloem tissues, which was demonstrated in the longer duration of probes and a trend toward longer duration of sap ingestion, respectively. M. persicae reached phloem in a shorter time on quercetin-treated B. rapa than on the control. Rutin caused a delay in reaching sieve elements by A. pisum and deterred probing activities of M. persicae within non-phloem tissues. Probing of R. padi was not affected by quercetin or rutin. The potency of behavioral effects increased as the applied concentrations of flavonols increased. The prospects of using quercetin and rutin in plant protection are discussed. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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11 pages, 658 KiB

Open AccessArticle

Impact of Altitudinal Variation on the Phytochemical Profile, Anthelmintic and Antimicrobial Activity of Two Pinus Species

by Wafaa M. Elkady, Mariam H. Gonaid, Miriam F. Yousif, Mahmoud El-Sayed and Hind A. N. Omar

Molecules 2021, 26(11), 3170; https://doi.org/10.3390/molecules26113170 - 26 May 2021

Cited by 12 | Viewed by 3255

Abstract

Active components from natural sources are the current focus in most pharmacological research to provide new therapeutic agents for clinical use. Essential oils from the Pinus species have been traditionally used in medicine. This study aimed to investigate the chemical profile of two [...] Read more.

Active components from natural sources are the current focus in most pharmacological research to provide new therapeutic agents for clinical use. Essential oils from the Pinus species have been traditionally used in medicine. This study aimed to investigate the chemical profile of two Pinus species, Pinus halepensis L. and Pinus pinea Mill, from different altitudes in Libya and study the effect of environmental conditions on the biological activities of essential oils. A clevenger apparatus was used to prepare the essential oils by hydrodistillation. Analyses were done using GC/MS. Anthelmintic and antimicrobial activities were tested against the earthworm Allolobophora caliginosa, gram-positive bacteria, gram-negative bacteria, and fungi. Different chemical profiles were observed among all tested essential oils, and terpenes were the most dominant class. All studied essential oils from the Pinus species exhibited a remarkable anthelmintic activity compared to the standard piperazine citrate drug. Pinus halepensis from both altitudes showed broad-spectrum antimicrobial activity against all tested microorganisms, while Pinus pinea was effective against only Escherichia coli. From these findings, one can conclude that there are variations between studied species. The essential oil compositions are affected by environmental factors, which consequently affect the anthelmintic and antimicrobial activity. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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16 pages, 1171 KiB

Open AccessArticle

Bioactivity-Guided Isolation of Phytochemicals from Vaccinium dunalianum Wight and Their Antioxidant and Enzyme Inhibitory Activities

by Tianrui Zhao, Mengxue Sun, Lingpeng Kong, Qingwang Xue, Yudan Wang, Yifen Wang, Afsar Khan, Jianxin Cao and Guiguang Cheng

Molecules 2021, 26(7), 2075; https://doi.org/10.3390/molecules26072075 - 4 Apr 2021

Cited by 23 | Viewed by 3055

Abstract

Vaccinium dunalianum Wight, usually processed as a traditional folk tea beverage, is widely distributed in the southwest of China. The present study aimed to investigate the antioxidant, ?-glucosidase and pancreatic lipase inhibitory activities of V.dunalianum extract and isolate the bioactive components. In [...] Read more.

Vaccinium dunalianum Wight, usually processed as a traditional folk tea beverage, is widely distributed in the southwest of China. The present study aimed to investigate the antioxidant, ?-glucosidase and pancreatic lipase inhibitory activities of V.dunalianum extract and isolate the bioactive components. In this study, the crude extract (CE) from the buds of V. dunalianum was prepared by the ultrasound-assisted extraction method in 70% methanol and then purified with macroporous resin D101 to obtain the purified extract (PM). Five fractions (Fr. A–E) were further obtained by MPLC column (RP-C18). Bioactivity assays revealed that Fr. B with 40% methanol and Fr. D with 80% methanol had better antioxidant with 0.48 ± 0.03 and 0.62 ± 0.01 nM Trolox equivalent (TE)/mg extract for DPPH, 0.87 ± 0.02 and 1.58 ± 0.02 nM TE/mg extract for FRAP, 14.42 ± 0.41 and 19.25 ± 0.23 nM TE/mg extract for ABTS, and enzyme inhibitory effects with IC₅₀ values of 95.21 ± 2.21 and 74.55 ± 3.85 for ?-glucosidase, and 142.53 ± 11.45 and 128.76 ± 13.85 µg/mL for pancreatic lipase. Multivariate analysis indicated that the TPC and TFC were positively related to the antioxidant activities. Further phytochemical purification led to the isolation of ten compounds (1–10). 6-O-Caffeoylarbutin (7) showed significant inhibitory effects on ?-glucosidase and pancreatic lipase enzymes with values of 38.38 ± 1.84 and 97.56 ± 7.53 µg/mL, and had the highest antioxidant capacity compared to the other compounds. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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20 pages, 1177 KiB

Open AccessArticle

Exploitation of Vitis vinifera, Foeniculum vulgare, Cannabis sativa and Punica granatum By-Product Seeds as Dermo-Cosmetic Agents

by Dimitris Michailidis, Apostolis Angelis, Panagiota Efstathia Nikolaou, Sofia Mitakou and Alexios Léandros Skaltsounis

Molecules 2021, 26(3), 731; https://doi.org/10.3390/molecules26030731 - 31 Jan 2021

Cited by 32 | Viewed by 5513

Abstract

In the current study, by-product seed pastes (VSPs) from Vitis vinifera, Foeniculum vulgare, Cannabis sativa and Punica granatum, generated during the oil production process, were investigated for their potential exploitation as dermo-cosmetic agent. The extraction pipeline of all the raw [...] Read more.

In the current study, by-product seed pastes (VSPs) from Vitis vinifera, Foeniculum vulgare, Cannabis sativa and Punica granatum, generated during the oil production process, were investigated for their potential exploitation as dermo-cosmetic agent. The extraction pipeline of all the raw materials was developed with emphasis on green methodologies and employed on laboratory scale based on industry-adopted techniques. Two different protocols were applied, Supercritical Fluid Extraction (SFE) and Ultrasound Assisted Extraction (UAE); the by-product pastes were defatted with supercritical CO₂ and n-Hexane, respectively. Then, two SFE extracts (CO₂ with 10% and 20% of ethanol as co-solvent) and two UAE extracts (with ethanol and ethanol/water 1:1 v/v) were obtained from each raw material. The providing yield range was between 2.6 to 76.3 mg/g raw material. The extracts were analyzed with High-Performance Liquid Chromatography coupled with Diode Array Detector (HPLC-DAD) and Liquid Chromatography coupled with High-Resolution Mass Spectrometer (LC-HRMS), and the major compounds, were identified. All the extracts were evaluated for their antioxidant and inhibition activity against collagenase, elastase and tyrosinase enzymes. Grapevine by-product extracts found rich in proanthocyanidins and presented the higher inhibition activity. A holistic green experimental methodology is proposed for the obtainment of extracts from significant medicinal plants by-products that provides us with promising results concerning dermo-cosmetic properties, especially for grape seeds extracts. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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20 pages, 4907 KiB

Open AccessArticle

New Anti-Leukemic Effect of Carvacrol and Thymol Combination through Synergistic Induction of Different Cell Death Pathways

by Fatima Bouhtit, Mehdi Najar, Douâa Moussa Agha, Rahma Melki, Mustapha Najimi, Khalid Sadki, Noureddine Boukhatem, Dominique Bron, Nathalie Meuleman, Abdellah Hamal, Laurence Lagneaux, Philippe Lewalle and Makram Merimi

Molecules 2021, 26(2), 410; https://doi.org/10.3390/molecules26020410 - 14 Jan 2021

Cited by 28 | Viewed by 4508

Abstract

Acute myeloid leukemia (AML) is a cancer of the myeloid lineage of blood cells, and treatment for AML is lengthy and can be very expensive. Medicinal plants and their bioactive molecules are potential candidates for improving human health. In this work, we studied [...] Read more.

Acute myeloid leukemia (AML) is a cancer of the myeloid lineage of blood cells, and treatment for AML is lengthy and can be very expensive. Medicinal plants and their bioactive molecules are potential candidates for improving human health. In this work, we studied the effect of Ptychotis verticillata (PV) essential oil and its derivatives, carvacrol and thymol, in AML cell lines. We demonstrated that a combination of carvacrol and thymol induced tumor cell death with low toxicity on normal cells. Mechanistically, we highlighted that different molecular pathways, including apoptosis, oxidative, reticular stress, autophagy, and necrosis, are implicated in this potential synergistic effect. Using quantitative RT-PCR, Western blotting, and apoptosis inhibitors, we showed that cell death induced by the carvacrol and thymol combination is caspase-dependent in the HL60 cell line and caspase-independent in the other cell lines tested. Further investigations should focus on improving the manufacturing of these compounds and understanding their anti-tumoral mechanisms of action. These efforts will lead to an increase in the efficiency of the oncotherapy strategy regarding AML. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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14 pages, 1427 KiB

Open AccessArticle

Melanogenesis Promoting Effect, Antioxidant Activity, and UPLC-ESI-HRMS Characterization of Phenolic Compounds of Argan Leaves Extract

by Thouria Bourhim, Myra O. Villareal, François Couderc, Abdellatif Hafidi, Hiroko Isoda and Chemseddoha Gadhi

Molecules 2021, 26(2), 371; https://doi.org/10.3390/molecules26020371 - 12 Jan 2021

Cited by 19 | Viewed by 4297

Abstract

The use of natural products for the regulation of skin pigmentation is gaining popularity. In the present study, we evaluated the effect of argan leaves extract (ALE) on melanogenesis in B16 melanoma cells, determined its antioxidant activity, then quantified and identified its phenolic [...] Read more.

The use of natural products for the regulation of skin pigmentation is gaining popularity. In the present study, we evaluated the effect of argan leaves extract (ALE) on melanogenesis in B16 melanoma cells, determined its antioxidant activity, then quantified and identified its phenolic components. B16 cells were treated with various concentrations of ALE, then the cell viability and proliferation were assessed using MTT assay while the melanin content was determined using spectrophotometric methods. The expression level of tyrosinase (TYR), tyrosinase related protein-1 (TRP-1) and dopachrome tautomerase (DCT) was evaluated by Western blotting. The antioxidant activity of ALE was investigated using four different assays while UPLC-ESI-HRMS analysis was used to characterize the ALE phenolic profile. Fourteen phenolic compounds were identified, of which six are reported for the first time to be present in ALE. ALE treatment increases the melanin content of B16 cells in a dose-dependent manner without cytotoxicity. This was revealed by the observed ALE-increased expression level of TYR, DCT, and TRP-1. These bioactivities may be mainly attributed to its high flavonoids content. Argan leaves have the potential for use as a treatment for hypopigmentation disorders and as a bioactive component of cosmetic products that aim to increase pigmentation. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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12 pages, 533 KiB

Open AccessArticle

Ocimum campechianum Mill. from Amazonian Ecuador: Chemical Composition and Biological Activities of Extracts and Their Main Constituents (Eugenol and Rosmarinic Acid)

by Massimo Tacchini, Monica Paulina Echeverria Guevara, Alessandro Grandini, Immacolata Maresca, Matteo Radice, Letizia Angiolella and Alessandra Guerrini

Molecules 2021, 26(1), 84; https://doi.org/10.3390/molecules26010084 - 27 Dec 2020

Cited by 15 | Viewed by 3956

Abstract

The essential oil (EO), the methanolic (MeOH), and the 70% ethanolic (70% EtOH) extracts obtained from the aerial parts of Ocimum campechianum Mill. (Ecuador) were chemically characterized through gas-chromatography coupled to mass spectrometry detector (GC-MS), high-performance liquid chromatography coupled to diode array-mass spectrometry [...] Read more.

The essential oil (EO), the methanolic (MeOH), and the 70% ethanolic (70% EtOH) extracts obtained from the aerial parts of Ocimum campechianum Mill. (Ecuador) were chemically characterized through gas-chromatography coupled to mass spectrometry detector (GC-MS), high-performance liquid chromatography coupled to diode array-mass spectrometry detectors (HPLC-DAD-MS) and studied for their in vitro biological activity. The radical scavenger activity, performed by spectrophotometric 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays, highlighted significant IC₅₀ values for the EO, extracts and their main constituents (eugenol and rosmarinic acid). EO (and eugenol) showed noteworthy activity against Pseudomonas syringae pv. syringae and a moderate effect against clinical Candida strains, with possible synergism in association to fluconazole against the latter microorganisms. The extracts and pure molecules exhibited weak cytotoxic activity against the HaCat cell line and no mutagenicity against Salmonella typhimurium TA98 and TA100 strains, giving indication of safety. Instead, EO showed a weak activity against adenocarcinomic human alveolar basal epithelial cells (A549). The above-mentioned evidence leads us to suggest a potential use of the crude drug, extracts, and EO in cosmetic formulation and food supplements as antioxidant agents. In addition, EO may also have a possible application in plant protection and anti-Candida formulations. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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11 pages, 1179 KiB

Open AccessArticle

Methylated Xanthones from the Rootlets of Metaxya rostrata Display Cytotoxic Activity in Colorectal Cancer Cells

by Eva Mittermair, Hanspeter Kählig, Ammar Tahir, Stefanie Rindler, Xenia Hudec, Hemma Schueffl, Petra Heffeter, Brigitte Marian and Liselotte Krenn

Molecules 2020, 25(19), 4449; https://doi.org/10.3390/molecules25194449 - 28 Sep 2020

Cited by 1 | Viewed by 2248

Abstract

The tree fern Metaxya rostrata (Kunth) C. Presl is common in the rainforests of Central and South America, where suspensions of the dried rhizome are traditionally used to treat intestinal diseases. Two compounds from this plant, 2-deprenyl-rheediaxanthone B (XB) and 2-deprenyl-7-hydroxy-rheediaxanthone B (OH-XB), [...] Read more.

The tree fern Metaxya rostrata (Kunth) C. Presl is common in the rainforests of Central and South America, where suspensions of the dried rhizome are traditionally used to treat intestinal diseases. Two compounds from this plant, 2-deprenyl-rheediaxanthone B (XB) and 2-deprenyl-7-hydroxy-rheediaxanthone B (OH-XB), have been shown to be biologically highly active against colorectal cancer (CRC) cells in previous studies. The current investigation resulted in the isolation of the previously undescribed methylated xanthones 2-deprenyl-6-O-methyl-7-hydroxy-rheediaxanthone B, 2-deprenyl-5-O-methyl-7-methoxy-rheediaxanthone B, 2-deprenyl-5-O-methyl- 7-hydroxy-rheediaxanthone B and 2-deprenyl-7-methoxy-rheediaxanthone B. All compounds were isolated by column chromatography, structures were elucidated by one- and two-dimensional NMR-experiments and the identities of the compounds were confirmed by LC-HRMS. In logarithmically growing SW480 CRC cell cultures, cytotoxicity by neutral red uptake and MTT assays as well as caspase activation was analyzed. Cellular targets were examined by Western blot, and topoisomerase I (topo I) inhibition potential was tested. Comparing the structure-activity relationship with XB and OH-XB, the monomethylated derivatives showed qualitatively similar effects/mechanisms to their nonmethylated analogues, while dimethylation almost abolished the activity. Inhibition of topo I was dependent on the presence of an unmethylated 7-OH group. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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17 pages, 11193 KiB

Open AccessArticle

Cytotoxic and Anti-Plasmodial Activities of Stephania dielsiana Y.C. Wu Extracts and the Isolated Compounds

by James Knockleby, Bruno Pradines, Mathieu Gendrot, Joel Mosnier, Thanh Tam Nguyen, Thi Thuy Trinh, Hoyun Lee and Phuong Mai Le

Molecules 2020, 25(16), 3755; https://doi.org/10.3390/molecules25163755 - 18 Aug 2020

Cited by 9 | Viewed by 3631

Abstract

Natural products remain a viable source of novel therapeutics, and as detection and extraction techniques improve, we can identify more molecules from a broader set of plant tissues. The aim of this study was an investigation of the cytotoxic and anti-plasmodial activities of [...] Read more.

Natural products remain a viable source of novel therapeutics, and as detection and extraction techniques improve, we can identify more molecules from a broader set of plant tissues. The aim of this study was an investigation of the cytotoxic and anti-plasmodial activities of the methanol extract from Stephania dielsiana Y.C. Wu leaves and its isolated compounds. Our study led to the isolation of seven alkaloids, among which oxostephanine (1) is the most active against several cancer cell lines including HeLa, MDA-MB231, MDA-MB-468, MCF-7, and non-cancer cell lines, such as 184B5 and MCF10A, with IC₅₀ values ranging from 1.66 to 4.35 μM. Morever, oxostephanine (1) is on average two-fold more active against cancer cells than stephanine (3), having a similar chemical structure. Cells treated with oxostephanine (1) are arrested at G2/M cell cycle, followed by the formation of aneuploidy and apoptotic cell death. The G2/M arrest appears to be due, at least in part, to the inactivation of Aurora kinases, which is implicated in the onset and progression of many forms of human cancer. An in-silico molecular modeling study suggests that oxostephanine (1) binds to the ATP binding pocket of Aurora kinases to inactivate their activities. Unlike oxostephanine (1), thailandine (2) is highly effective against only the triple-negative MDA-MB-468 breast cancer cells. However, it showed excellent selectivity against the cancer cell line when compared to its effects on non-cancer cells. Furthermore, thailandine (2) showed excellent anti-plasmodial activity against both chloroquine-susceptible 3D7 and chloroquine-resistant W2 Plasmodium falciparum strains. The structure–activity relationship of isolated compound was also discussed in this study. The results of this study support the traditional use of Stephania dielsiana Y.C. Wu and the lead molecules identified can be further optimized for the development of highly effective and safe anti-cancer and anti-plasmodial drugs. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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25 pages, 7099 KiB

Open AccessArticle

Studies to Elucidate the Mechanism of Cardio Protective and Hypotensive Activities of Anogeissus acuminata (Roxb. ex DC.) in Rodents

by Fatima Saqib, Muhammad Arif Aslam, Khizra Mujahid, Luigi Marceanu, Marius Moga, Hanadi Talal Ahmedah and Liana Chicea

Molecules 2020, 25(15), 3471; https://doi.org/10.3390/molecules25153471 - 30 Jul 2020

Cited by 7 | Viewed by 3477

Abstract

Anogeissus acuminata (Roxb. ex DC.) is a folkloric medicinal plant in Asia; including Pakistan; used as a traditional remedy for cardiovascular disorders. This study was planned to establish a pharmacological basis for the trivial uses of Anogeissus acuminata in certain medical conditions related [...] Read more.

Anogeissus acuminata (Roxb. ex DC.) is a folkloric medicinal plant in Asia; including Pakistan; used as a traditional remedy for cardiovascular disorders. This study was planned to establish a pharmacological basis for the trivial uses of Anogeissus acuminata in certain medical conditions related to cardiovascular systems and to explore the underlying mechanisms. Mechanistic studies suggested that crude extract of Anogeissus acuminata (Aa.Cr) produced in vitro cardio-relaxant and vasorelaxant effects in isolated paired atria and aorta coupled with in vivo decrease in blood pressure by invasive method; using pressure and force transducers connected to Power Lab Data Acquisition System. Moreover; Aa.Cr showed positive effects in left ventricular hypertrophy in Sprague Dawley rats observed hemodynamically by a decrease in cardiac cell size and fibrosis; along with absence of inflammatory cells; coupled with reduced levels of angiotensin converting enzyme (ACE) and renin concentration along with increased concentrations of nitric oxide (NO) and cyclic guanosine monophosphate (cGMP). In Acute Myocardial Infarction (AMI) model; creatine kinase (CK), creatine kinase-MB (CK-MB) and lactic acid dehydrogenase (LDH levels) were found to be decreased; along with decreased necrosis; edema and recruitment of inflammatory cells histologically. In vivo and ex vivo studies of Anogeissus acuminata provided evidence of vasorelaxant; hypotensive and cardioprotective properties facilitated through blockage of voltage-gated Ca⁺⁺ ion channel; validating its use in cardiovascular diseases Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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9 pages, 240 KiB

Open AccessArticle

Study on Lavender Essential Oil Chemical Compositions by GC-MS and Improved pGC

by Guangyao Dong, Xiaohui Bai, Aoken Aimila, Haji Akber Aisa and Maitinuer Maiwulanjiang

Molecules 2020, 25(14), 3166; https://doi.org/10.3390/molecules25143166 - 10 Jul 2020

Cited by 54 | Viewed by 8179

Abstract

Lavender essential oil from the aerial parts of Lavandula angustifolia Mill. was analyzed by GC-MS equipped with three capillary columns of different polarities, which were HP-1, HP-5 ms and HP-INNOWax. A total of 40 compounds were identified by GC-MS, accounting for 92.03% of [...] Read more.

Lavender essential oil from the aerial parts of Lavandula angustifolia Mill. was analyzed by GC-MS equipped with three capillary columns of different polarities, which were HP-1, HP-5 ms and HP-INNOWax. A total of 40 compounds were identified by GC-MS, accounting for 92.03% of the total essential oil compositions. Nineteen monomers were separated by column chromatography and improved preparative gas chromatography (pGC), six of which could not be retrieved from the NIST 14 (National Institute of Standards and Technology, USA; 14th edition) library database. Fifteen compounds were identified for the first time in lavender essential oil. The improved pGC not only doubled the efficiency but also greatly reduced the cost. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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Zebrafish and Flavonoids: Adjuvants against Obesity

by Giuseppe Montalbano, Kamel Mhalhel, Marilena Briglia, Maria Levanti, Francesco Abbate, Maria Cristina Guerrera, Enrico D’Alessandro, Rosaria Laurà and Antonino Germanà

Molecules 2021, 26(10), 3014; https://doi.org/10.3390/molecules26103014 - 19 May 2021

Cited by 13 | Viewed by 5422

Abstract

Obesity is a pathological condition, defined as an excessive accumulation of fat, primarily caused by an energy imbalance. The storage of excess energy in the form of triglycerides within the adipocyte leads to lipotoxicity and promotes the phenotypic switch in the M1/M2 macrophage. [...] Read more.

Obesity is a pathological condition, defined as an excessive accumulation of fat, primarily caused by an energy imbalance. The storage of excess energy in the form of triglycerides within the adipocyte leads to lipotoxicity and promotes the phenotypic switch in the M1/M2 macrophage. These changes induce the development of a chronic state of low-grade inflammation, subsequently generating obesity-related complications, commonly known as metabolic syndromes. Over the past decade, obesity has been studied in many animal models. However, due to its competitive aspects and unique characteristics, the use of zebrafish has begun to gain traction in experimental obesity research. To counteract obesity and its related comorbidities, several natural substances have been studied. One of those natural substances reported to have substantial biological effects on obesity are flavonoids. This review summarizes the results of studies that examined the effects of flavonoids on obesity and related diseases and the emergence of zebrafish as a model of diet-induced obesity. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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A Chewable Cure “Kanna”: Biological and Pharmaceutical Properties of Sceletium tortuosum

by Madira Coutlyne Manganyi, Cornelius Carlos Bezuidenhout, Thierry Regnier and Collins Njie Ateba

Molecules 2021, 26(9), 2557; https://doi.org/10.3390/molecules26092557 - 28 Apr 2021

Cited by 13 | Viewed by 9897

Abstract

Sceletium tortuosum (L.) N.E.Br. (Mesembryanthemaceae), commonly known as kanna or kougoed, is an effective indigenous medicinal plant in South Africa, specifically to the native San and Khoikhoi tribes. Today, the plant has gained strong global attraction and reputation due to its capabilities to [...] Read more.

Sceletium tortuosum (L.) N.E.Br. (Mesembryanthemaceae), commonly known as kanna or kougoed, is an effective indigenous medicinal plant in South Africa, specifically to the native San and Khoikhoi tribes. Today, the plant has gained strong global attraction and reputation due to its capabilities to promote a sense of well-being by relieving stress with calming effects. Historically, the plant was used by native San hunter-gatherers and Khoi people to quench their thirst, fight fatigue and for healing, social, and spiritual purposes. Various studies have revealed that extracts of the plant have numerous biological properties and isolated alkaloids of Sceletium tortuosum are currently being used as dietary supplements for medicinal purposes and food. Furthermore, current research has focused on the commercialization of the plant because of its treatment in clinical anxiety and depression, psychological and psychiatric disorders, improving mood, promoting relaxation and happiness. In addition, several studies have focused on the isolation and characterization of various beneficial bioactive compounds including alkaloids from the Sceletium tortuosum plant. Sceletium was reviewed more than a decade ago and new evidence has been published since 2008, substantiating an update on this South African botanical asset. Thus, this review provides an extensive overview of the biological and pharmaceutical properties of Sceletium tortuosum as well as the bioactive compounds with an emphasis on antimicrobial, anti-inflammatory, anti-oxidant, antidepressant, anxiolytic, and other significant biological effects. There is a need to critically evaluate the bioactivities and responsible bioactive compounds, which might assist in reinforcing and confirming the significant role of kanna in the promotion of healthy well-being in these stressful times. Full article

(This article belongs to the Special Issue Medicinal and Aromatic Plants as Source of Bioactive Compounds: Chemical Characterization and Bioactivity)

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