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9 pages, 1864 KiB

Open AccessCommunication

Activation of Hair Cell Growth Factors by Linoleic Acid in Malva verticillata Seed

by Hwa Sun Ryu, JiYeon Jeong, Chun Mong Lee, Kwang Sik Lee, Jung-No Lee, Sung-Min Park and Yong-Moon Lee

Molecules 2021, 26(8), 2117; https://doi.org/10.3390/molecules26082117 - 7 Apr 2021

Cited by 19 | Viewed by 4753

Abstract

Hair loss by excessive stress from work and lifestyle changes has become a growing concern, particularly among young individuals. However, most drugs for alopecia impose a plethora of side effects. We have found the powerful impact of Malva verticillata seed extracts on alleviating [...] Read more.

Hair loss by excessive stress from work and lifestyle changes has become a growing concern, particularly among young individuals. However, most drugs for alopecia impose a plethora of side effects. We have found the powerful impact of Malva verticillata seed extracts on alleviating hair loss. This study further isolated effective chemicals in M. verticillata seed extracts by liquid silica gel column chromatography. Under the screening for the growth rate (%) of human follicles dermal papilla cells (HFDPCs), we identified linoleic acid (LA) and oleic acid in n-hexane of M. verticillate (MH)2 fraction. LA treatment activated Wnt/β-catenin signaling and induced HFDPCs growth by increasing the expression of cell cycle proteins such as cyclin D1 and cyclin-dependent kinase 2. LA treatment also increased several growth factors, such as vascular endothelial growth factor, insulin-like growth factor-1, hepatocyte growth factor, and keratinocyte growth factor, in a dose-dependent manner. Besides, LA significantly inhibited Dickkopf-related protein expression (DKK-1), a primary alopecia signaling by dihydrotestosterone. Our findings suggest that LA treatment may alleviate a testosterone-induced signaling molecule and induces HFDPCs growth by activating Wnt/β-catenin signaling. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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15 pages, 2549 KiB

Open AccessFeature PaperArticle

A White Grape Juice Extract Reduces Fat Accumulation through the Modulation of Ghrelin and Leptin Expression in an In Vivo Model of Overfed Zebrafish

by Giuseppe Montalbano, Alessandro Maugeri, Maria Cristina Guerrera, Natalizia Miceli, Michele Navarra, Davide Barreca, Santa Cirmi and Antonino Germanà

Molecules 2021, 26(4), 1119; https://doi.org/10.3390/molecules26041119 - 20 Feb 2021

Cited by 17 | Viewed by 3249

Abstract

A caloric surplus and a sedentary lifestyle are undoubtedly known to be the leading causes of obesity. Natural products represent valuable allies to face this problematic issue. This study was planned to assess the effect of a white grape (Vitis vinifera) [...] Read more.

A caloric surplus and a sedentary lifestyle are undoubtedly known to be the leading causes of obesity. Natural products represent valuable allies to face this problematic issue. This study was planned to assess the effect of a white grape (Vitis vinifera) juice extract (WGJe) in diet-induced obese zebrafish (Danio rerio). Fish were divided into four different diet groups: (i) normally fed (NF); (ii) overfed (OF); (iii) WGJe-supplemented NF (5 mL/L in fish water); (iv) WGJe-supplemented OF. Body mass index (BMI) was extrapolated each week. After the fourth week, euthanized zebrafish were processed for both microscopic evaluations and gene expression analyses. OF zebrafish showed higher BMI values with respect to NF counterparts, an effect that was hindered by WGJe treatment. Moreover, histological analyses showed that the area of the adipose tissue, as well as the number, size, and density of adipocytes was significantly higher in OF fish. On the other hand, WGJe was able to avoid these outcomes both at the subcutaneous and visceral levels, albeit to different extents. At the gene level, WGJe restored the altered levels of ghrelin and leptin of OF fish both in gut and brain. Overall, our results support the anti-obesity property of WGJe, suggesting its potential role in weight management. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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25 pages, 2948 KiB

Open AccessArticle

11-Keto-α-Boswellic Acid, a Novel Triterpenoid from Boswellia spp. with Chemotaxonomic Potential and Antitumor Activity against Triple-Negative Breast Cancer Cells

by Michael Schmiech, Judith Ulrich, Sophia Johanna Lang, Berthold Büchele, Christian Paetz, Alexis St-Gelais, Tatiana Syrovets and Thomas Simmet

Molecules 2021, 26(2), 366; https://doi.org/10.3390/molecules26020366 - 12 Jan 2021

Cited by 28 | Viewed by 6094

Abstract

Boswellic acids, and particularly 11-keto-boswellic acids, triterpenoids derived from the genus Boswellia (Burseraceae), are known for their anti-inflammatory and potential antitumor efficacy. Although boswellic acids generally occur as α-isomers (oleanane type) and β-isomers (ursane type), 11-keto-boswellic acid (KBA) was found only [...] Read more.

Boswellic acids, and particularly 11-keto-boswellic acids, triterpenoids derived from the genus Boswellia (Burseraceae), are known for their anti-inflammatory and potential antitumor efficacy. Although boswellic acids generally occur as α-isomers (oleanane type) and β-isomers (ursane type), 11-keto-boswellic acid (KBA) was found only as the β-isomer, β-KBA. Here, the existence and natural occurrence of the respective α-isomer, 11-keto-α-boswellic acid (α-KBA), is demonstrated for the first time. Initially, α-KBA was synthesized and characterized by high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy, and a highly selective, sensitive, and accurate high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) method was developed by Design of Experiments (DoE) using a pentafluorophenyl stationary phase. This method allowed the selective quantification of individual 11-keto-boswellic acids and provided evidence for α-KBA in Boswellia spp. oleogum resins. The contents of α-KBA as well as further boswellic acids and the composition of essential oils were used to chemotaxonomically classify 41 Boswellia oleogum resins from 9 different species. Moreover, α-KBA exhibited cytotoxicity against three treatment-resistant triple-negative breast cancer (TNBC) cell lines in vitro and also induced apoptosis in MDA-MB-231 xenografts in vivo. The respective β-isomer and the acetylated form demonstrate higher cytotoxic efficacies against TNBC cells. This provides further insights into the structure-activity relationship of boswellic acids and could support future developments of potential anti-inflammatory and antitumor drugs. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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21 pages, 3443 KiB

Open AccessArticle

Phytochemistry and Biological Activities of Iris Species Growing in Iraqi Kurdistan and Phenolic Constituents of the Traditional Plant Iris postii

by Hawraz Ibrahim M. Amin, Faiq H. S. Hussain, Soran K. Najmaldin, Zaw Min Thu, Mohammed Farhad Ibrahim, Gianluca Gilardoni and Giovanni Vidari

Molecules 2021, 26(2), 264; https://doi.org/10.3390/molecules26020264 - 7 Jan 2021

Cited by 20 | Viewed by 3634

Abstract

A dozen Iris species (Iridaceae) are considered traditional remedies in Kurdistan, especially for treating inflammations. Phytochemical studies are still scarce. The information reported in the literature about Iris species growing in Kurdistan has been summarized in the first part of this paper, although, [...] Read more.

A dozen Iris species (Iridaceae) are considered traditional remedies in Kurdistan, especially for treating inflammations. Phytochemical studies are still scarce. The information reported in the literature about Iris species growing in Kurdistan has been summarized in the first part of this paper, although, except for Iris persica, investigations have been performed on vegetal samples collected in countries different from Kurdistan. In the second part of the work, we have investigated, for the first time, the contents of the methanolic extracts of Iris postii aerial parts and rhizomes that were collected in Kurdistan. Both extracts exhibited a significant dose-dependent free radical scavenging and total antioxidant activities, comparable to those of ascorbic acid. Medium-pressure liquid chromatographic separations of the two extracts afforded l-tryptophan, androsin, isovitexin, swertisin, and 2″-O-α-l-rhamnopyranosyl swertisin from the aerial parts, whereas ε-viniferin, trans-resveratrol 3,4′-O-di-β-d-glucopyranoside, and isotectorigenin were isolated from the rhizomes. This is the first finding of the last three metabolites from an Iris species. The various remarkable biological activities of isolated compounds scientifically sustain the traditional use of I. postii as a medicinal plant. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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15 pages, 2405 KiB

Open AccessArticle

Development of HPLC Method for Quantification of Sinigrin from Raphanus sativus Roots and Evaluation of Its Anticancer Potential

by Anroop B. Nair, Dipal Gandhi, Snehal S. Patel, Mohamed A. Morsy, Bapi Gorain, Mahesh Attimarad and Jigar N. Shah

Molecules 2020, 25(21), 4947; https://doi.org/10.3390/molecules25214947 - 26 Oct 2020

Cited by 3 | Viewed by 3130

Abstract

Sinigrin, a precursor of allyl isothiocyanate, present in the Raphanus sativus exhibits diverse biological activities, and has an immense role against cancer proliferation. Therefore, the objective of this study was to quantify the sinigrin in the R. sativus roots using developed and validated [...] Read more.

Sinigrin, a precursor of allyl isothiocyanate, present in the Raphanus sativus exhibits diverse biological activities, and has an immense role against cancer proliferation. Therefore, the objective of this study was to quantify the sinigrin in the R. sativus roots using developed and validated RP-HPLC method and further evaluated its’ anticancer activity. To achieve the objective, the roots of R. sativus were lyophilized to obtain a stable powder, which were extracted and passed through an ion-exchange column to obtain sinigrin-rich fraction. The RP-HPLC method using C18 analytical column was used for chromatographic separation and quantification of sinigrin in the prepared fraction, which was attained using the mobile phase consisting of 20 mM tetrabutylammonium: acetonitrile (80:20%, v/v at pH 7.0) at a flow rate of 0.5 mL/min. The chromatographic peak for sinigrin was showed at 3.592 min for pure sinigrin, where a good linearity was achieved within the concentration range of 50 to 800 µg/mL (R² > 0.99), with an excellent accuracy (−1.37% and −1.29%) and precision (1.43% and 0.94%), for intra and inter-day, respectively. Finally, the MTT assay was performed for the sinigrin-rich fraction using three different human cancer cell lines, viz. prostate cancer (DU-145), colon adenocarcinoma (HCT-15), and melanoma (A-375). The cell-based assays were extended to conduct apoptotic and caspase-3 activities, to determine the mechanism of action of sinigrin in the treatment of cancer. MTT assay showed IC₅₀ values of 15.88, 21.42, and 24.58 µg/mL for DU-145, HCT-15, and A-375 cell lines, respectively. Increased cellular apoptosis and caspase-3 expression were observed with sinigrin-rich fraction, indicating significant increase in overexpression of caspase-3 in DU-145 cells. In conclusion, a simple, sensitive, fast, and accurate RP-HPLC method was developed for the estimation of sinigrin in the prepared fraction. The data observed here indicate that sinigrin can be beneficial in treating prostate cancer possibly by inducing apoptosis. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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18 pages, 1865 KiB

Open AccessArticle

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities

by I Gusti Agung Ayu Kartika, In Jae Bang, Catur Riani, Muhamad Insanu, Jong Hwan Kwak, Kyu Hyuck Chung and I Ketut Adnyana

Molecules 2020, 25(21), 4914; https://doi.org/10.3390/molecules25214914 - 23 Oct 2020

Cited by 8 | Viewed by 4599

Abstract

Extracts of Peperomia pellucida [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate [...] Read more.

Extracts of Peperomia pellucida [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate and elucidate potential compounds with estrogenic activity. The structures of the isolated compounds were identified using 1D ¹H and ¹³C-NMR and confirmed by 2D FT-NMR. The estrogenic activity was evaluated using the E-SCREEN assay, and a molecular docking study was performed to predict the binding affinity of the isolated compounds to estrogen receptors. In this experiment, we successfully isolated three phenylpropanoids and two lignan derivatives, namely, 6-allyl-5-methoxy-1,3-benzodioxol-4-ol (1), pachypostaudin B (2), pellucidin A (3), dillapiole (4), and apiol (5). Among these compounds, the isolation of 1 and 2 from P. pellucida is reported for the first time in this study. Activity assays clearly showed that the ethyl acetate extract and its fractions, subfractions, and isolated compounds exerted estrogenic activity. Methanol fraction of the ethyl acetate extract produced the highest estrogenic activity, while 1 and 2 had partial agonist activity. Some compounds (derivates of dillapiole and pellucidin A) also had, in addition, anti-estrogenic activity. In the docking study, the estrogenic activities of 1–5 appeared to be mediated by a classical ligand-dependent mechanism as suggested by the binding interaction between the compounds and estrogen receptors; binding occurred on Arg 394 and His 524 of the alpha receptor and Arg 346 and His 475 of the beta receptor. In summary, we reveal that P. pellucida is a promising anti-osteoporotic agent due to its estrogenic activity, and the compounds responsible for this activity were found to be lignan and phenylpropanoid derivatives. The presence of other compounds in either the extract or fraction may contribute to a synergistic effect, as suggested by the higher estrogenic activity of the methanol fraction. Hence, we suggest further research on the osteoporotic activity and safety of the identified compounds, especially regarding their effects on estrogen-responsive organs. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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19 pages, 2819 KiB

Open AccessArticle

Essential Oils from Monarda fistulosa: Chemical Composition and Activation of Transient Receptor Potential A1 (TRPA1) Channels

by Monica Ghosh, Igor A. Schepetkin, Gulmira Özek, Temel Özek, Andrei I. Khlebnikov, Derek S. Damron and Mark T. Quinn

Molecules 2020, 25(21), 4873; https://doi.org/10.3390/molecules25214873 - 22 Oct 2020

Cited by 22 | Viewed by 4670

Abstract

Little is known about the pharmacological activity of Monarda fistulosa L. essential oils. To address this issue, we isolated essential oils from the flowers and leaves of M. fistulosa and analyzed their chemical composition. We also analyzed the pharmacological effects of M. fistulosa [...] Read more.

Little is known about the pharmacological activity of Monarda fistulosa L. essential oils. To address this issue, we isolated essential oils from the flowers and leaves of M. fistulosa and analyzed their chemical composition. We also analyzed the pharmacological effects of M. fistulosa essential oils on transient receptor potential (TRP) channel activity, as these channels are known targets of various essential oil constituents. Flower (MEO_Fl) and leaf (MEO_Lv) essential oils were comprised mainly of monoterpenes (43.1% and 21.1%) and oxygenated monoterpenes (54.8% and 77.7%), respectively, with a high abundance of monoterpene hydrocarbons, including p-cymene, γ-terpinene, α-terpinene, and α-thujene. Major oxygenated monoterpenes of MEO_Fl and MEO_Lv included carvacrol and thymol. Both MEO_Fl and MEO_Lv stimulated a transient increase in intracellular free Ca²⁺ concentration ([Ca²⁺]_i) in TRPA1 but not in TRPV1 or TRPV4-transfected cells, with MEO_Lv being much more effective than MEO_Fl. Furthermore, the pure monoterpenes carvacrol, thymol, and β-myrcene activated TRPA1 but not the TRPV1 or TRPV4 channels, suggesting that these compounds represented the TRPA1-activating components of M. fistulosa essential oils. The transient increase in [Ca²⁺]_i induced by MEO_Fl/MEO_Lv, carvacrol, β-myrcene, and thymol in TRPA1-transfected cells was blocked by a selective TRPA1 antagonist, HC-030031. Although carvacrol and thymol have been reported previously to activate the TRPA1 channels, this is the first report to show that β-myrcene is also a TRPA1 channel agonist. Finally, molecular modeling studies showed a substantial similarity between the docking poses of carvacrol, thymol, and β-myrcene in the binding site of human TRPA1. Thus, our results provide a cellular and molecular basis to explain at least part of the therapeutic properties of these essential oils, laying the foundation for prospective pharmacological studies involving TRP ion channels. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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12 pages, 1692 KiB

Open AccessArticle

1,6-Dehydropinidine Is an Abundant Compound in Picea abies (Pinaceae) Sprouts and 1,6-Dehydropinidine Fraction Shows Antibacterial Activity against Streptococcus equi Subsp. equi

by Virpi Virjamo, Pia Fyhrquist, Akseli Koskinen, Anu Lavola, Katri Nissinen and Riitta Julkunen-Tiitto

Molecules 2020, 25(19), 4558; https://doi.org/10.3390/molecules25194558 - 6 Oct 2020

Cited by 7 | Viewed by 2636

Abstract

Knowledge about the defensive chemistry of coniferous trees has increased in recent years regarding a number of alkaloid compounds; in addition to phenolics and terpenes. Here, we show that Norway spruce (Picea abies (L.) H. Karst.), an important boreal zone tree species; [...] Read more.

Knowledge about the defensive chemistry of coniferous trees has increased in recent years regarding a number of alkaloid compounds; in addition to phenolics and terpenes. Here, we show that Norway spruce (Picea abies (L.) H. Karst.), an important boreal zone tree species; accumulates 1,6-dehydropinidine (2-methyl-6-(2-propenyl)-1,6-piperideine) in its needles and bark. We reanalyzed previously published GC-MS data to obtain a full picture of 1,6-dehydropinidine in P. abies. 1,6-dehydropinidine appeared to especially accumulate in developing spring shoots. We used solid-phase partitioning to collect the alkaloid fraction of the sprouts and thin-layer chromatography to purify 1,6-dehydropinidine. The antibacterial properties of the 1,6-dehydropinidine fraction were tested using a broth microdilution method; with Streptococcus equi subsp. equi as a model organism. Based on our results 1,6-dehydropinidine is common in alkaloid extractions from P. abies (0.4 ± 0.03 mg g⁻¹ dw in mature needles) and it is especially abundant in young spruce shoots (2.7 ± 0.5 mg g⁻¹ dw). Moreover; 1,6-dehydropinidine extracted from P. abies sprouts showed mild antibacterial potential against Streptococcus equi subsp. equi (MIC 55 µg mL⁻¹). The antibacterial activity of a plant compound thought of as an intermediate rather than an end-product of biosynthesis calls for more detailed studies regarding the biological function of these coniferous alkaloids Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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8 pages, 1148 KiB

Open AccessCommunication

Salumycin, a New Pyrazolequinone from a Streptomyces albus J1074 Mutant Strain

by Kaixiang Tao, Taijia Ye, Mingming Cao, Xiaolu Meng, Yuqing Li, Huan Wang and Zhiyang Feng

Molecules 2020, 25(18), 4098; https://doi.org/10.3390/molecules25184098 - 8 Sep 2020

Cited by 1 | Viewed by 2435

Abstract

Heterocyclic natural products with various bioactivities play significant roles in pharmaceuticals. Here, we isolated a heterocyclic compound salumycin (1) from a Streptomyces albus J1074 mutant strain. The structure of (1) was elucidated via single-crystal X-ray diffraction, mass spectrometry (MS), [...] Read more.

Heterocyclic natural products with various bioactivities play significant roles in pharmaceuticals. Here, we isolated a heterocyclic compound salumycin (1) from a Streptomyces albus J1074 mutant strain. The structure of (1) was elucidated via single-crystal X-ray diffraction, mass spectrometry (MS), fourier transform infrared spectrometer (FTIR), and nuclear magnetic resonance (NMR) data analysis. Salumycin (1) contained a novel pyrazolequinone ring, which had never been previously reported in a natural product. Salumycin (1) exhibited moderate 2,2′-diphenyl-1-picrylhydrazyl (DPPH)-radical scavenging activity (EC50 = 46.3 ± 2.2 μM) compared with tert-butylhydroquinone (EC50 = 4.7 ± 0.3 μM). This study provides a new example of discovering novel natural products from bacteria. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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21 pages, 5716 KiB

Open AccessArticle

Biological Activity and Antibiofilm Molecular Profile of Citrus aurantium Essential Oil and Its Application in a Food Model

by Miroslava Kačániová, Margarita Terentjeva, Lucia Galovičová, Eva Ivanišová, Jana Štefániková, Veronika Valková, Petra Borotová, Przemysław Łukasz Kowalczewski, Simona Kunová, Soňa Felšöciová, Eva Tvrdá, Jana Žiarovská, Renáta Benda Prokeinová and Nenad Vukovic

Molecules 2020, 25(17), 3956; https://doi.org/10.3390/molecules25173956 - 30 Aug 2020

Cited by 46 | Viewed by 4813

Abstract

The main aim of the study was to investigate the chemical composition, antioxidant, antimicrobial, and antibiofilm activity of Citrus aurantium essential oil (CAEO). The biofilm profile of Stenotrophonomonas maltophilia and Bacillus subtilis were assessed using the mass spectrometry MALDI-TOF MS Biotyper and the [...] Read more.

The main aim of the study was to investigate the chemical composition, antioxidant, antimicrobial, and antibiofilm activity of Citrus aurantium essential oil (CAEO). The biofilm profile of Stenotrophonomonas maltophilia and Bacillus subtilis were assessed using the mass spectrometry MALDI-TOF MS Biotyper and the antibiofilm activity of Citrus aurantium (CAEO) was studied on wood and glass surfaces. A semi-quantitative composition using a modified version was applied for the CAEO characterization. The antioxidant activity of CAEO was determined using the DPPH method. The antimicrobial activity was analyzed by disc diffusion for two biofilm producing bacteria, while the vapor phase was used for three penicillia. The antibiofilm activity was observed with the agar microdilution method. The molecular differences of biofilm formation on different days were analyzed, and the genetic similarity was studied with dendrograms constructed from MSP spectra to illustrate the grouping profiles of S. maltophilia and B. subtilis. A differentiated branch was obtained for early growth variants of S. maltophilia for planktonic cells and all experimental groups. The time span can be reported for the grouping pattern of B. subtilis preferentially when comparing to the media matrix, but without clear differences among variants. Furthermore, the minimum inhibitory doses of the CAEO were investigated against microscopic fungi. The results showed that CAEO was most active against Penicillium crustosum, in the vapor phase, on bread and carrot in situ. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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9 pages, 458 KiB

Open AccessArticle

Acylated Flavone O-Glucuronides from the Aerial Parts of Nepeta curviflora

by Maysaa Rabee, Øyvind Moksheim Andersen, Torgils Fossen, Kjersti Hasle Enerstvedt, Hijazi Abu Ali and Saleh Rayyan

Molecules 2020, 25(17), 3782; https://doi.org/10.3390/molecules25173782 - 20 Aug 2020

Cited by 7 | Viewed by 3425

Abstract

Nepeta curviflora Boiss. (Syrian catnip) is native to the Middle East. This medicinal plant is commonly used against nervous disorders, rheumatic pains, and high blood pressure. Herbal infusions prepared from various Nepeta spp. are extensively consumed as functional food. However, limited information has [...] Read more.

Nepeta curviflora Boiss. (Syrian catnip) is native to the Middle East. This medicinal plant is commonly used against nervous disorders, rheumatic pains, and high blood pressure. Herbal infusions prepared from various Nepeta spp. are extensively consumed as functional food. However, limited information has been known about the phenolic constituents of Syrian catnip. In this study, two acylated flavone 7-O-glucuronides, apigenin 7-O-(2″-O-(2‴-(E-caffeoyl)-β-glucuronopyranosyl)-β-glucuronopyranoside) (1) and luteolin 7-O-(2″-O-(2‴-(E-caffeoyl)-β-glucuronopyranosyl)-β-glucuronopyranoside) (2), along with the known phenolic compounds rosmarinic acid, caffeic acid, apigenin, and apigenin 7-O-β-glucopyranoside were isolated from the aerial parts of N. curviflora. The characterizations of these compounds were based on high-resolution mass spectrometry, UV, and extensive use of multidimensional NMR spectroscopy. The new compounds (1 and 2) were identified in the unmodified state and as dimethylesters. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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13 pages, 2130 KiB

Open AccessArticle

Rindera graeca (Boraginaceae) Phytochemical Profile and Biological Activities

by Christos Ganos, Nektarios Aligiannis, Ioanna Chinou, Nikolaos Naziris, Maria Chountoulesi, Tomasz Mroczek and Konstantia Graikou

Molecules 2020, 25(16), 3625; https://doi.org/10.3390/molecules25163625 - 9 Aug 2020

Cited by 15 | Viewed by 4256

Abstract

Rindera graeca is a Greek endemic plant of the Boraginaceae family which has never been studied before. Consequently, this study attempted to phytochemically examine the aerial parts of this species. Nine phenolic secondary metabolites were identified, consisting of seven caffeic acid derivatives and [...] Read more.

Rindera graeca is a Greek endemic plant of the Boraginaceae family which has never been studied before. Consequently, this study attempted to phytochemically examine the aerial parts of this species. Nine phenolic secondary metabolites were identified, consisting of seven caffeic acid derivatives and two flavonol glucosides, namely rutin and quercetin-3-rutinoside-7-rhamnoside. These flavonoids, together with rosmarinic acid, were isolated via column chromatography and structurally determined through spectral analysis. Quercetin-3-rutinoside-7-rhamnoside is an unusual triglycoside, which is identified for the first time in Rindera genus and among Boraginaceae plants. This metabolite was further examined with thermal analysis and its 3D structure was simulated, revealing some intriguing information on its interaction with biological membrane models, which might have potential applications in microcirculation-related conditions. R. graeca was also analyzed for its pyrrolizidine alkaloids content, and it was found to contain echinatine together with echinatine N-oxide and rinderine N-oxide. Additionally, the total phenolic and flavonoid contents of R. graeca methanol extract were determined, along with free radical inhibition assays. High total phenolic content and almost complete inhibition at experimental doses at the free radical assays indicate a potent antioxidant profile for this plant. Overall, through phytochemical analysis and biological activity assays, insight was gained on an endemic Greek species of the little-studied Rindera genus, while its potential for further applications has been assessed. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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21 pages, 7031 KiB

Open AccessArticle

Production of Encecalin in Cell Cultures and Hairy Roots of Helianthella quinquenervis (Hook.) A. Gray

by J. Mabel Hernández-Altamirano, Irene F. Ugidos, Javier Palazón, Mercedes Bonfill, Penélope García-Angulo, Jesús Álvarez, José L. Acebes, Robert Bye and Antonio Encina

Molecules 2020, 25(14), 3231; https://doi.org/10.3390/molecules25143231 - 15 Jul 2020

Cited by 6 | Viewed by 3098

Abstract

Plant cell and organ cultures of Helianthella quinquenervis, a medicinal plant whose roots are used by the Tarahumara Indians of Chihuahua, Mexico, to relieve several ailments, were established to identify and quantify some chromenes with biological activity, such as encecalin, and to [...] Read more.

Plant cell and organ cultures of Helianthella quinquenervis, a medicinal plant whose roots are used by the Tarahumara Indians of Chihuahua, Mexico, to relieve several ailments, were established to identify and quantify some chromenes with biological activity, such as encecalin, and to evaluate their potential for biotechnological production. Gas chromatography–mass spectrometry (GC-MS) analysis corroborated the presence of quantifiable amounts of encecalin in H. quinquenervis cell cultures (callus and cell suspensions). In addition, hairy roots were obtained through three transformation protocols (prick, 45-s sonication and co-culture), using wild type Agrobacterium rhizogenes A4. After three months, cocultivation achieved the highest percentage of transformation (66%), and a comparable production (FW) of encecalin (110 μg/g) than the sonication assay (120 μg/g), both giving far higher yields than the prick assay (19 μg/g). Stable integration of rolC and aux1 genes in the transformed roots was confirmed by polymerase chain reaction (PCR). Hairy roots from cocultivation (six months-old) accumulated as much as 1086 μg/g (FW) of encecalin, over three times higher than the cell suspension cultures. The production of encecalin varied with growth kinetics, being higher at the stationary phase. This is the first report of encecalin production in hairy roots of H. quinquenervis, demonstrating the potential for a future biotechnological production of chromenes. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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13 pages, 1748 KiB

Open AccessArticle

Bioassay Guided Isolation and Docking Studies of a Potential β-Lactamase Inhibitor from Clutia myricoides

by Mahmoud A. Elfaky, Ali M. El-Halawany, Abdulrahman E. Koshak, Khalid Z. Alshali, Moustafa E. El-Araby, Maan T. Khayat and Hossam M. Abdallah

Molecules 2020, 25(11), 2566; https://doi.org/10.3390/molecules25112566 - 31 May 2020

Cited by 12 | Viewed by 3191

Abstract

Infectious diseases are the second major cause of death worldwide, and the ability to resist multiple classes of antibiotics is the key factor in enabling pathogenic organisms to survive and spread in the nosocomial environment. Unfortunately, the available β-lactamase inhibitors are not efficient [...] Read more.

Infectious diseases are the second major cause of death worldwide, and the ability to resist multiple classes of antibiotics is the key factor in enabling pathogenic organisms to survive and spread in the nosocomial environment. Unfortunately, the available β-lactamase inhibitors are not efficient against β-lactamase B, C, and D which necessitates discovering either broad spectrum β-lactamase inhibitors or new β-lactam antibiotics resistant to bacterial enzymes. In this regard, products of natural origin have prompted the disclosure of new compounds and medicinal leads. Chloroform fraction of Clutia myricoides (Soa’bor) showed a pronounced activity against extended-spectrum β-lactamase (ESBL) strains. Bio-guided fractionation resulted in isolation of two new compounds; 2-methoxy chrysophanol (2) and Saudin-I (5) in addition to three known compounds that were identified as chrysophanol (1), stigmasterol (3) and β-sitosterol (4). Antibacterial and anti ESBL activities of the isolated compounds were performed. No antibacterial activities were detected for any of the tested compounds. Meanwhile, compound 2 showed promising anti ESBL activity. Compound 2 has shown an obvious activity against K. pneumoniae ATCC 700603 with a marked enlargement of inhibition zones (>5mm) in combination with third generation cephalosporin antibiotics. To further understand the mechanism of action of compound 2, molecular docking was carried out against CTX-M-27 ESBL. The results showed binding site interactions strikingly different from its analogue, compound 1, allowing compound 2 to be active against ESBL. These results proposed the concomitant use of these active compounds with antibiotics that would increase their efficiency. Nevertheless, the interaction between this active compound and antibiotics should be taken into consideration. Therefore, in order to evaluate the safety of this active compound, further in vitro and in vivo toxicity assays must be carried out. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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15 pages, 950 KiB

Open AccessArticle

Bioactive Potential of Extracts of Labrenzia aggregata Strain USBA 371, a Halophilic Bacterium Isolated from a Terrestrial Source

by Carolina Díaz-Cárdenas, Laura Yinneth Rojas, Susana Fiorentino, Monica P. Cala, Jorge I Díaz, Freddy A. Ramos, Jean Armengaud, Silvia Restrepo and Sandra Baena

Molecules 2020, 25(11), 2546; https://doi.org/10.3390/molecules25112546 - 29 May 2020

Cited by 4 | Viewed by 4254

Abstract

Previous studies revealed the potential of Labrenzia aggregata USBA 371 to produce cytotoxic metabolites. This study explores its metabolic diversity and compounds involved in its cytotoxic activity. Extracts from the extracellular fraction of strain USBA 371 showed high levels of cytotoxic activity associated [...] Read more.

Previous studies revealed the potential of Labrenzia aggregata USBA 371 to produce cytotoxic metabolites. This study explores its metabolic diversity and compounds involved in its cytotoxic activity. Extracts from the extracellular fraction of strain USBA 371 showed high levels of cytotoxic activity associated with the production of diketopiperazines (DKPs). We purified two compounds and a mixture of two other compounds from this fraction. Their structures were characterized by 1D and 2D nuclear magnetic resonance (NMR). The purified compounds were evaluated for additional cytotoxic activities. Compound 1 (cyclo (l-Pro-l-Tyr)) showed cytotoxicity to the following cancer cell lines: breast cancer 4T1 (IC₅₀ 57.09 ± 2.11 µM), 4T1H17 (IC₅₀ 40.38 ± 1.94), MCF-7 (IC₅₀ 87.74 ± 2.32 µM), murine melanoma B16 (IC₅₀ 80.87 ± 3.67), human uterus sarcoma MES-SA/Dx5 P-pg (−) (IC₅₀ 291.32 ± 5.64) and MES-SA/Dx5 P-pg (+) (IC₅₀ 225.28 ± 1.23), and murine colon MCA 38 (IC₅₀ 29.85 ± 1.55). In order to elucidate the biosynthetic route of the production of DKPs and other secondary metabolites, we sequenced the genome of L. aggregata USBA 371. We found no evidence for biosynthetic pathways associated with cyclodipeptide synthases (CDPSs) or non-ribosomal peptides (NRPS), but based on proteogenomic analysis we suggest that they are produced by proteolytic enzymes. This is the first report in which the cytotoxic effect of cyclo (l-Pro-l-Tyr) produced by an organism of the genus Labrenzia has been evaluated against several cancer cell lines. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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12 pages, 1759 KiB

Open AccessArticle

Five New Pregnane Glycosides from Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities

by Phan Van Kiem, Duong Thi Hai Yen, Nguyen Van Hung, Nguyen Xuan Nhiem, Bui Huu Tai, Do Thi Trang, Pham Hai Yen, Tran Minh Ngoc, Chau Van Minh, SeonJu Park, Jae Hyuk Lee, Sun Yeou Kim and Seung Hyun Kim

Molecules 2020, 25(11), 2525; https://doi.org/10.3390/molecules25112525 - 28 May 2020

Cited by 13 | Viewed by 3659

Abstract

Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A–E (1–5) and four known [...] Read more.

Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A–E (1–5) and four known oleanane saponins, 3β-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (6), gymnemoside-W1 (7), 3β-O-β-D-xylopyranosyl-(1→6)-β-D- glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (8), and alternoside XIX (9). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds 2–4 showed significant α-amylase inhibitory activity, with IC₅₀ values ranging from 113.0 to 176.2 µM. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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8 pages, 1360 KiB

Open AccessCommunication

Gastroprotective Effect of Juanislamin on Ethanol-Induced Gastric Lesions in Rats: Role of Prostaglandins, Nitric Oxide and Sulfhydryl Groups in the Mechanism of Action

by María Elena Sánchez-Mendoza, Yaraset López-Lorenzo, Leticia Cruz-Antonio, Arturo Cruz-Oseguera, Jazmín García-Machorro and Jesús Arrieta

Molecules 2020, 25(9), 2246; https://doi.org/10.3390/molecules25092246 - 10 May 2020

Cited by 12 | Viewed by 2917

Abstract

Peptic ulcer disease, the most common gastrointestinal disorder, is currently treated with several types of drugs, but all have severe side effects. The aim of the present study was to evaluate the gastroprotective activity of juanislamin, isolated from Calea urticifolia, in a [...] Read more.

Peptic ulcer disease, the most common gastrointestinal disorder, is currently treated with several types of drugs, but all have severe side effects. The aim of the present study was to evaluate the gastroprotective activity of juanislamin, isolated from Calea urticifolia, in a rat model of ethanol-induced gastric lesions. Thirty minutes after orally administering a given dose of juanislamin (from 1 to 30 mg/kg) or carbenoxolone (the reference drug, at 1–100 mg/kg) to rats, 1 mL of ethanol was applied, and the animals were sacrificed 2 h later. The stomachs were removed and opened to measure the total area of lesions in each. To examine the possible participation of prostaglandins, nitric oxide and/or sulfhydryl groups in the mechanism of action of juanislamin, the rats received indomethacin, NG-Nitro-l-arginine methyl ester hydrochloride (l-NAME) or N-ethylmaleimide pretreatment, respectively, before being given juanislamin and undergoing the rest of the methodology. Juanislamin inhibited gastric lesions produced by ethanol in a non-dose-dependent manner, showing the maximum gastroprotective effect (100%) at 10 mg/kg. The activity of juanislamin was not modified by pretreatment with indomethacin, l-NAME or N-ethylmaleimide. In conclusion, juanislamin protected the gastric mucosa from ethanol-induced damage, and its mechanism of action apparently does not involve prostaglandins, nitric oxide or sulfhydryl groups. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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14 pages, 1532 KiB

Open AccessArticle

Identification of Transient Receptor Potential Vanilloid 3 Antagonists from Achillea alpina L. and Separation by Liquid-Liquid-Refining Extraction and High-Speed Counter-Current Chromatography

by Shi-Wei Sun, Rong-Rong Wang, Xiao-Ying Sun, Jia-He Fan, Hang Qi, Yang Liu, Guo-Qing Qin and Wei Wang

Molecules 2020, 25(9), 2025; https://doi.org/10.3390/molecules25092025 - 26 Apr 2020

Cited by 9 | Viewed by 2913

Abstract

Bioassay-guided fractionation of the ethanol extract of whole herbs of Achillea alpina led to the isolation of isochlorogenic acids A and B as transient receptor potential vanilloid 3 (TRPV3) channel antagonists by using a calcium fluorescent assay. The structures were identified by spectroscopic [...] Read more.

Bioassay-guided fractionation of the ethanol extract of whole herbs of Achillea alpina led to the isolation of isochlorogenic acids A and B as transient receptor potential vanilloid 3 (TRPV3) channel antagonists by using a calcium fluorescent assay. The structures were identified by spectroscopic analysis and the inhibitory activities of isochlorogenic acids A and B were confirmed by whole-cell patch clamp recordings of human embryonic kidney 293 (HEK293) cells expressing human TRPV3. Molecular docking results revealed that these two compounds reside in the same active pocket of human TRPV3 channel protein with lower binding energy than the agonist 2-aminoethoxydiphenyl borate (2-APB). High-speed counter-current chromatography (HSCCC) coupled with a liquid-liquid extraction approach was successfully established for the separation of isochlorogenic acids A and B from the whole herbs of A. alpina. Ethyl acetate and n-hexane-ethyl acetate-water (3:3:4 and 1:5:4, v/v/v) were selected as liquid-liquid extraction solvent systems to remove high- and low-polarity impurities in the mixture. Sixty g of ethanol extract was refined by solvent partition to yield 1.7 g of the enriched fraction, of which 480 mg in turn obtained 52.5 mg of isochlorogenic acid B (purity 98.3%) and 37.6 mg isochlorogenic acid A (purity 96.2%) after HSCCC with n-hexane-ethyl acetate-water containing 1% acetic acid (1:4:8, v/v/v). Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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24 pages, 4102 KiB

Open AccessArticle

Optimization of Ultrasound-Assisted Extraction Using Response Surface Methodology for Simultaneous Quantitation of Six Flavonoids in Flos Sophorae Immaturus and Antioxidant Activity

by Sanhong Fan, Gege Yang, Jinhua Zhang, Jiani Li and Baoqing Bai

Molecules 2020, 25(8), 1767; https://doi.org/10.3390/molecules25081767 - 12 Apr 2020

Cited by 45 | Viewed by 6579

Abstract

Ultrasound-assisted extraction (UAE) was applied to extract rutin (RU), nicotiflorin (NI), narcissoside (NA), kaempferol (KA), isorhamnetin (IS), quercetin (QU), and total flavonoids of Flos Sophorae Immaturus (TFFSI) from Flos Sophorae Immaturus (FSI). Through single factor test and response surface methodology (RSM), the optimal [...] Read more.

Ultrasound-assisted extraction (UAE) was applied to extract rutin (RU), nicotiflorin (NI), narcissoside (NA), kaempferol (KA), isorhamnetin (IS), quercetin (QU), and total flavonoids of Flos Sophorae Immaturus (TFFSI) from Flos Sophorae Immaturus (FSI). Through single factor test and response surface methodology (RSM), the optimal extraction conditions were concluded as follows: ethanol concentration 70%, time 30 min, temperature 61 °C, and liquid/solid ratio 15.30 mL/g, respectively. The actual extraction rates of RU, NI, NA, KA, IS, QU, and TFFSI were 14.6101%, 2.9310%, 7.1987%, 0.1041%, 0.4920%, 2.7998%, and 26.4260%, respectively. The experimental results demonstrated that the extraction method with accuracy and efficiency could be used for the comprehensive evaluation quality control of extracts from FSI. The antioxidant activities of hydroalcoholic extraction from FSI on 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•⁺), superoxide anion (•O²⁻) free radicals, and ferric reducing/antioxidant power (FRAP) were assessed. The results showed that the antioxidation activities of extracts on DPPH, ABTS•⁺, and •O²⁻ free radicals were reached 89.29%, 97.86%, and 56.61%, and 81.4% in FRAP at 1.0 mg/mL, respectively. The antioxidant capacity of FSI extract was positively correlated with the amount of total flavonoids. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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11 pages, 1389 KiB

Open AccessArticle

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

by Rosa Mariana Montiel-Ruiz, Marcos Córdova-de la Cruz, Manasés González-Cortázar, Alejandro Zamilpa, Abraham Gómez-Rivera, Ricardo López-Rodríguez, Carlos Ernesto Lobato-García and Ever A. Blé-González

Molecules 2020, 25(6), 1454; https://doi.org/10.3390/molecules25061454 - 24 Mar 2020

Cited by 10 | Viewed by 3216

Abstract

Aristolochia odoratissima L. is employed for the treatment of pain and as an antidote against the poison of venomous animals in traditional medicine. However, reports have not been found, to our knowledge, about the evaluation of the antinociceptive activity of extracts nor about [...] Read more.

Aristolochia odoratissima L. is employed for the treatment of pain and as an antidote against the poison of venomous animals in traditional medicine. However, reports have not been found, to our knowledge, about the evaluation of the antinociceptive activity of extracts nor about the presence of compounds associated with this activity. Thus, the purpose of this work was to evaluate the antinociceptive activity of extracts and compounds isolated from the stems of Artistolochia odoratissima L. The extracts were obtained with solvents of increasing polarity and the compounds were isolated and characterized by column chromatography, HPLC, and NMR. The antinociceptive activity was carried out by the formalin test in mice. Ethyl acetate (AoEA) and methanolic (AoM) extracts decreased the paw licking in both phases of the formalin test. The isolated compounds (kaurenoic acid and hinokinin) from AoEA showed the highest antinociceptive activity in both phases of the formalin test. These results confirmed the analgesic effect of this specie described in traditional medicine and provided a base for a novel analgesic agent. They also allowed an approach for the development of standardized plant extracts with isolated metabolites. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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13 pages, 2094 KiB

Open AccessArticle

Effect of Terpenoids and Flavonoids Isolated from Baccharis conferta Kunth on TPA-Induced Ear Edema in Mice

by Gutiérrez-Román Ana Silvia, Trejo-Tapia Gabriela, Herrera-Ruiz Maribel, Monterrosas-Brisson Nayeli, Trejo-Espino José Luis, Zamilpa Alejandro and González-Cortazar Manasés

Molecules 2020, 25(6), 1379; https://doi.org/10.3390/molecules25061379 - 18 Mar 2020

Cited by 12 | Viewed by 6037

Abstract

In this study, we isolated from the aerial parts of Baccharis conferta Kunth (i) a new neoclerodane, denominated “bacchofertone”; (ii) four known terpenes: schensianol A, bacchofertin, kingidiol and oleanolic acid; and (iii) two flavonoids: cirsimaritin and hispidulin. All structures were identified by an [...] Read more.

In this study, we isolated from the aerial parts of Baccharis conferta Kunth (i) a new neoclerodane, denominated “bacchofertone”; (ii) four known terpenes: schensianol A, bacchofertin, kingidiol and oleanolic acid; and (iii) two flavonoids: cirsimaritin and hispidulin. All structures were identified by an exhaustive analysis of nuclear magnetic resonance (NMR) and mass spectroscopy (MS). Extracts from aerial parts were screened for anti-inflammatory activity in the mice ear edema model of 12-O-tetradecanoylforbol-13-acetate mice. Dichloromethane extract (BcD) exhibited 78.5 ± 0.72% inhibition of edema, followed by the BcD2 and BcD3 fractions of 71.4% and 82.9% respectively, at a dose of 1 mg/ear. Kingidiol and cirsimaritin were the most potent compounds identified, with a median effective dose of 0.12 and 0.16 mg/ear, respectively. A histological analysis showed that the topical application of TPA promoted intense cell infiltration, and this inflammatory parameter was reduced with the topical application of isolated compounds. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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14 pages, 4621 KiB

Open AccessArticle

Cucurbitacin E Inhibits Huh7 Hepatoma Carcinoma Cell Proliferation and Metastasis via Suppressing MAPKs and JAK/STAT3 Pathways

by Yang Liu, Heng Yang, Qiang Guo, Tingting Liu, Yong Jiang, Mingbo Zhao, Kewu Zeng and Pengfei Tu

Molecules 2020, 25(3), 560; https://doi.org/10.3390/molecules25030560 - 28 Jan 2020

Cited by 36 | Viewed by 4249

Abstract

Cucurbitacin E (CuE), a highly oxygenated tetracyclic triterpene from Cucurbitaceae, has shown to exhibit potent cytotoxic and anti-proliferative properties against several human cancer cells. However, the underlying effects and mechanisms of CuE regarding hepatocellular carcinoma (HCC) have not been well understood. In the [...] Read more.

Cucurbitacin E (CuE), a highly oxygenated tetracyclic triterpene from Cucurbitaceae, has shown to exhibit potent cytotoxic and anti-proliferative properties against several human cancer cells. However, the underlying effects and mechanisms of CuE regarding hepatocellular carcinoma (HCC) have not been well understood. In the current study, unbiased RNA-sequencing (RNA-seq) and bioinformatics analysis was applied to elucidate the underlying molecular mechanism. CuE could significantly inhibit cell proliferation and migration of Huh7 cells, meanwhile CuE exhibited potent anti-angiogenic activity. RNA-seq analysis revealed that CuE negatively regulated 241 differentially expressed genes (DEGs) involved in multiple processes including cytoskeleton formation, angiogenesis and focal adhesion. Further analysis revealed that CuE effectually regulated diversified pharmacological signaling pathways such as MAPKs and JAK-STAT3. Our findings demonstrated the role of CuE in inhibiting proliferation and migration, providing an insight into the regulation of multiple signaling pathways as a new paradigm for anti-cancer treatment strategy. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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14 pages, 1644 KiB

Open AccessArticle

Bioassay-Guided Isolation and HPLC Quantification of Antiproliferative Metabolites from Stahlianthus thorelii

by Nham-Linh Nguyen, Thanh-Hoa Vo, Yu-Chi Lin, Chia-Ching Liaw, Zhi-Hu Lin, Mei-Chuan Chen and Yao-Haur Kuo

Molecules 2020, 25(3), 551; https://doi.org/10.3390/molecules25030551 - 28 Jan 2020

Cited by 6 | Viewed by 4120

Abstract

In folk medicine, Stahlianthus thorelii Gagnep. has been used to treat diseases related to inflammation, ulcers, and cancer. There are no reports concerning the chemical components and bioactivities of S. thorelii; thus, this study aims to explore the phytochemicals, quantify the main [...] Read more.

In folk medicine, Stahlianthus thorelii Gagnep. has been used to treat diseases related to inflammation, ulcers, and cancer. There are no reports concerning the chemical components and bioactivities of S. thorelii; thus, this study aims to explore the phytochemicals, quantify the main compounds, and test the anticancer activity of isolates from S. thorelii. Dried rhizomes were extracted with 95% ethanol and, then, partitioned, fractionated, and isolated. On the basis of the result of the antiproliferative activity of the fractions, seven isolates were yielded and were identified by spectroscopic analyses. The inhibition of cancer proliferation was determined by an MTT assay and the deployed IC₅₀ to value their efficacy. Seven compounds containing one new C-benzylated dihydrochalcone derivative, thorechalcone A (1) and 2–7 were isolated from S. thorelii. In terms of the bioactivity, compounds 1 and 3 displayed promising antiproliferative activity (WiDr, A549, and HepG2), with IC₅₀ values <40 µM. The HPLC-UV method of quantification of two major compounds (3 and 4) was also validated. This study presented the isolations of antiproliferative potentials of new chalcone and known flavonoid derivatives from S. thorelii. The validated simple, accurate, and rapid HPLC method could be deployed for the quality control of herbal drugs. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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Review

Jump to: Research

44 pages, 3750 KiB

Open AccessReview

Recent Clinical and Preclinical Studies of Hydroxychloroquine on RNA Viruses and Chronic Diseases: A Systematic Review

by Immacolata Faraone, Fabiana Labanca, Maria Ponticelli, Nunziatina De Tommasi and Luigi Milella

Molecules 2020, 25(22), 5318; https://doi.org/10.3390/molecules25225318 - 14 Nov 2020

Cited by 11 | Viewed by 6028

Abstract

The rapid spread of the new Coronavirus Disease 2019 (COVID-19) has actually become the newest challenge for the healthcare system since, to date, there is not an effective treatment. Among all drugs tested, Hydroxychloroquine (HCQ) has attracted significant attention. This systematic review aims [...] Read more.

The rapid spread of the new Coronavirus Disease 2019 (COVID-19) has actually become the newest challenge for the healthcare system since, to date, there is not an effective treatment. Among all drugs tested, Hydroxychloroquine (HCQ) has attracted significant attention. This systematic review aims to analyze preclinical and clinical studies on HCQ potential use in viral infection and chronic diseases. A systematic search of Scopus and PubMed databases was performed to identify clinical and preclinical studies on this argument; 2463 papers were identified and 133 studies were included. Regarding HCQ activity against COVID-19, it was noticed that despite the first data were promising, the latest outcomes highlighted the ineffectiveness of HCQ in the treatment of viral infection. Several trials have seen that HCQ administration did not improve severe illness and did not prevent the infection outbreak after virus exposure. By contrast, HCQ arises as a first-line treatment in managing autoimmune diseases such as rheumatoid arthritis, lupus erythematosus, and Sjögren syndrome. It also improves glucose and lipid homeostasis and reveals significant antibacterial activity. Full article

(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity)

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