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9 pages, 571 KiB

Open AccessArticle

Quantitative HPLC–UV Study of Lignans in Anthriscus sylvestris

by Dejan Orčić, Sanja Berežni and Neda Mimica-Dukić

Molecules 2022, 27(18), 6072; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27186072 - 17 Sep 2022

Cited by 5 | Viewed by 1262

Wild chervil (Anthriscus sylvestris) is a wild-growing plant from the Apiaceae family, used as a food in Europe and eastern Asia. Due to its high content of lignans known to possess anti-inflammatory, antiproliferative, antiviral and other activities, it represents a potential [...] Read more.

Wild chervil (Anthriscus sylvestris) is a wild-growing plant from the Apiaceae family, used as a food in Europe and eastern Asia. Due to its high content of lignans known to possess anti-inflammatory, antiproliferative, antiviral and other activities, it represents a potential functional food. However, quantitative data on lignans are still scarce and limited to deoxypodophyllotoxin, nemerosin and yatein. In this paper, a newly developed and validated reverse-phase HPLC–UV method was used to evaluate the content of 14 lignans in both aerial parts and roots of A. sylvestris. The most abundant root components were found to be deoxypodophyllotoxin (2.0–42.8 mg/g), nemerosin (2.0–23.4 mg/g), yatein (1.1–18.5 mg/g), podophyllotoxone (0.7–20.5 mg/g), guaiadequiol (0.8–8.3 mg/g) and dimethylmatairesinol (0.1–5.2 mg/g). Despite the high intra-population variability, a general trend of an increased lignan content during plant development could be observed in the root samples, whereas an opposite trend was observed in the herb samples. A validation study indicated that some of the investigated compounds—7-oxoaryltetralins and dibenzylbutyrolactones—have low stability and require cold storage in the dark. Furthermore, dibenzylbutyrolactones were confirmed to undergo a fast cis–trans isomerization; therefore, only the total content of these isomers should be reported. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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20 pages, 2719 KiB

Open AccessArticle

Phytochemical Evaluation and Anti-Inflammatory Potential of Miconia albicans (Sw.) Triana Extracts

by Mariana Inocencio Manzano, Ariana Centa, Alan de Almeida Veiga, Nayara Souza da Costa, Sandro J. R. Bonatto, Lauro M. de Souza and Fhernanda Ribeiro Smiderle

Molecules 2022, 27(18), 5954; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27185954 - 13 Sep 2022

Cited by 1 | Viewed by 1664

Abstract

The plant Miconia albicans (Sw.) Triana has been popularly used in Brazil to treat chronic inflammatory disturbances, such as osteoarthritis. This disease affects 250 million people worldwide, and is associated with intense pain and loss of articular function. There is a lack of [...] Read more.

The plant Miconia albicans (Sw.) Triana has been popularly used in Brazil to treat chronic inflammatory disturbances, such as osteoarthritis. This disease affects 250 million people worldwide, and is associated with intense pain and loss of articular function. There is a lack of information about the phytochemistry and bioactivity of M. albicans. Therefore, this study determined the chemical composition of some extracts and evaluated their cytotoxicity, along with their antioxidant and anti-inflammatory, activities using in vitro models. Aqueous and ethanolic extracts were prepared. Afterwards, a liquid–liquid partition was developed using chloroform, ethyl acetate, and n-butanol. The extracts were characterized by LC–MS, and their biological activities were evaluated on epithelial cells (Vero), tumoral hepatic cells (Hep-G2), and THP-1 macrophages. LC–MS analyses identified several flavonoids in all fractions, such as quercetin, myricetin, and their glycosides. The crude extracts and n-butanol fractions did not present cytotoxicity to the cells. The non-toxic fractions presented significant antioxidant activity when evaluated in terms of DPPH scavenging activity, lipid peroxidation, and ROS inhibition. THP-1 macrophages treated with the n-butanol fraction (250 µg/mL) released fewer pro-inflammatory cytokines, even in the presence of LPS. In the future, it will be necessary to identify the phytochemicals that are responsible for anti-inflammatory effects for the discovery of new drugs. In vivo studies on M. albicans extracts are still required to confirm their possible mechanisms of action. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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16 pages, 7186 KiB

Open AccessArticle

The Evaluation of Healing Properties of Galium verum-Based Oral Gel in Aphthous Stomatitis in Rats

by Miona Vuletic, Vladimir Jakovljevic, Suzana Zivanovic, Milos Papic, Mirjana Papic, Rasa Mladenovic, Vladimir Zivkovic, Ivan Srejovic, Jovana Jeremic, Marijana Andjic, Aleksandar Kocovic, Jasmina Sretenovic, Slobodanka Mitrovic, Biljana Božin, Nebojša Kladar, Sergey Bolevich and Jovana Bradic

Molecules 2022, 27(15), 4680; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27154680 - 22 Jul 2022

Cited by 4 | Viewed by 2099

Abstract

Although oral ulcers represent one of the most frequent oral mucosal diseases, the available treatment is not sufficient to provide complete ulcer recovery without side-effects. Therefore, the aim of our study was to prepare a mucoadhesive oral gel based on Galium verum ethanol [...] Read more.

Although oral ulcers represent one of the most frequent oral mucosal diseases, the available treatment is not sufficient to provide complete ulcer recovery without side-effects. Therefore, the aim of our study was to prepare a mucoadhesive oral gel based on Galium verum ethanol extract (GVL gel) and reveal its healing effects in the model of aphthous stomatitis in rats. Rats with oral ulcers were divided into the following groups: control (untreated), gel base (ulcer was treated with the gel base, three times per day for 10 days), and GVL gel group (the ulcer was treated with GVL gel in the same way as the gel base). Animals from each group were sacrificed on days 0, 3, 6, and 10 for collecting blood and ulcer tissue samples. Healing properties of oral gel were determined by clinical evaluation, as well as biochemical and histopathological examinations. Our findings suggest a significant decrease in the ulcer size in GVL gel group, with healing effects achieved through the alleviation of oxidative stress, reduction in COX-2 immunopositivity, and increase in collagen content in buccal tissue. Significant ulcer repairing potential of GVL gel highlights this oral mucoadhesive gel as a promising tool for prevention and treatment of RAS. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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11 pages, 2830 KiB

Open AccessArticle

Rutin Inhibits Ox-LDL-Mediated Macrophage Inflammation and Foam Cell Formation by Inducing Autophagy and Modulating PI3K/ATK Signaling

by Ben Li, Yumeng Ji, Chenlong Yi, Xufeng Wang, Chaoyang Liu, Chufan Wang, Xiaohu Lu, Xiaohan Xu and Xiaowei Wang

Molecules 2022, 27(13), 4201; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27134201 - 29 Jun 2022

Cited by 9 | Viewed by 2256

Abstract

Atherosclerosis (AS) is one of the leading causes of death among the elderly, and is primarily caused by foam cell generation and macrophage inflammation. Rutin is an anti-inflammatory, anti-oxidant, anti-allergic, and antiviral flavonoid molecule, known to have anti-atherosclerotic and autophagy-inducing properties, but its [...] Read more.

Atherosclerosis (AS) is one of the leading causes of death among the elderly, and is primarily caused by foam cell generation and macrophage inflammation. Rutin is an anti-inflammatory, anti-oxidant, anti-allergic, and antiviral flavonoid molecule, known to have anti-atherosclerotic and autophagy-inducing properties, but its biological mechanism remains poorly understood. In this study, we uncovered that rutin could suppress the generation of inflammatory factors and reactive oxygen species (ROS) in ox-LDL-induced M2 macrophages and enhance their polarization. Moreover, rutin could decrease foam cell production, as shown by oil red O staining. In addition, rutin could increase the number of autophagosomes and the LC3II/I ratio, while lowering p62 expression. Furthermore, rutin could significantly inhibit the PI3K/ATK signaling pathway. In summary, rutin inhibits ox-LDL-mediated macrophage inflammation and foam cell formation by inducing autophagy and modulating PI3K/ATK signaling, showing potential in treating atherosclerosis. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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16 pages, 11663 KiB

Open AccessArticle

Hispidulin Ameliorates Endotoxin-Induced Acute Kidney Injury in Mice

by Kiryeong Kim and Jaechan Leem

Molecules 2022, 27(6), 2019; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27062019 - 21 Mar 2022

Cited by 12 | Viewed by 2712

Abstract

Lipopolysaccharide (LPS) is an endotoxin that plays a crucial role in septic acute kidney injury (AKI). Hispidulin is a natural flavonoid that possesses various biological activities. Recent studies have shown that hispidulin administration alleviates various inflammatory diseases in animal models. This study aimed [...] Read more.

Lipopolysaccharide (LPS) is an endotoxin that plays a crucial role in septic acute kidney injury (AKI). Hispidulin is a natural flavonoid that possesses various biological activities. Recent studies have shown that hispidulin administration alleviates various inflammatory diseases in animal models. This study aimed to investigate the renoprotective effect of hispidulin on LPS-induced AKI. Male C57BL/6 mice were administered LPS (10 mg/kg) with or without hispidulin (50 mg/kg). Hispidulin administration attenuated renal dysfunction, histological alterations, and the upregulation of neutrophil gelatinase-associated lipocalin. This flavonoid also reduced cytokine production and Toll-like receptor 4 expression, inhibited nuclear factor-κB and mitogen-activated protein kinase cascades, and alleviated immune cell infiltration. The oxidation of lipids and DNA was also inhibited by hispidulin administration. This antioxidant effect of hispidulin was associated with the downregulation of NADPH oxidase 4, the activation of catalase and superoxide dismutase activities, and the restoration of glutathione levels. Moreover, hispidulin administration attenuated tubular cell apoptosis by inhibiting caspase-3 pathway. These data suggest that hispidulin ameliorates endotoxin-induced kidney injury by suppressing inflammation, oxidative stress, and tubular cell death. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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13 pages, 2934 KiB

Open AccessArticle

Estrogenic Activity of Mycoestrogen (3β,5α,22E)-Ergost-22-en-3-ol via Estrogen Receptor α-Dependent Signaling Pathways in MCF-7 Cells

by Dahae Lee, Yuri Ko, Changhyun Pang, Yoon-Joo Ko, You-Kyoung Choi, Ki Hyun Kim and Ki Sung Kang

Molecules 2022, 27(1), 36; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010036 - 22 Dec 2021

Cited by 7 | Viewed by 2213

Abstract

Armillariella tabescens (Scop.) Sing., a mushroom of the family Tricholomataceae, has been used in traditional oriental medicine to treat cholecystitis, improve bile secretion, and regulate bile-duct pressure. The present study evaluated the estrogen-like effects of A. tabescens using a cell-proliferation assay in [...] Read more.

Armillariella tabescens (Scop.) Sing., a mushroom of the family Tricholomataceae, has been used in traditional oriental medicine to treat cholecystitis, improve bile secretion, and regulate bile-duct pressure. The present study evaluated the estrogen-like effects of A. tabescens using a cell-proliferation assay in an estrogen-receptor-positive breast cancer cell line (MCF-7). We found that the methanol extract of A. tabescens fruiting bodies promoted cell proliferation in MCF-7 cells. Using bioassay-guided fractionation of the methanol extract and chemical investigation, we isolated and identified four steroids and four fatty acids from the active fraction. All eight compounds were evaluated by E-screen assay for their estrogen-like effects in MCF-7 cells. Among the tested isolates, only (3β,5α,22E)-ergost-22-en-3-ol promoted cell proliferation in MCF-7 cells; this effect was mitigated by the ER antagonist, ICI 182,780. The mechanism underlying the estrogen-like effect of (3β,5α,22E)-ergost-22-en-3-ol was evaluated using Western blot analysis to detect the expression of extracellular signal-regulated kinase (ERK), phosphatidylinositol 3-kinase (PI3K), Akt, and estrogen receptor α (ERα). We found that (3β,5α,22E)-ergost-22-en-3-ol induced an increase in phosphorylation of ERK, PI3K, Akt, and ERα. Together, these experimental results suggest that (3β,5α,22E)-ergost-22-en-3-ol is responsible for the estrogen-like effects of A. tabescens and may potentially aid control of estrogenic activity in menopause. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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14 pages, 968 KiB

Open AccessArticle

Chromane Derivatives from Underground Parts of Iris tenuifolia and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation

by Oldokh Otgon, Suvd Nadmid, Christian Paetz, Hans-Martin Dahse, Kerstin Voigt, Stefan Bartram, Wilhelm Boland and Enkhmaa Dagvadorj

Molecules 2021, 26(21), 6705; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216705 - 05 Nov 2021

Cited by 2 | Viewed by 1867

Abstract

Phytochemical investigation of the ethanol extract of underground parts of Iris tenuifolia Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (1), 5-methoxy-6,7-methylenedioxy-4-O-2′-cycloflavan (2), 5,7,2′,3′-tetrahydroxyflavanone (3), 5-hydroxy-6,7-dimethoxyisoflavone-2′-O-β-d-glucopyranoside ( [...] Read more.

Phytochemical investigation of the ethanol extract of underground parts of Iris tenuifolia Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (1), 5-methoxy-6,7-methylenedioxy-4-O-2′-cycloflavan (2), 5,7,2′,3′-tetrahydroxyflavanone (3), 5-hydroxy-6,7-dimethoxyisoflavone-2′-O-β-d-glucopyranoside (9), 5,2′,3′-dihydroxy-6,7-dimethoxyisoflavone (10), along with seven known compounds (4–8, 11–12). The structures of all purified compounds were established by analysis of 1D and 2D NMR spectroscopy and HR-ESI-MS. The antimicrobial activity of the compounds 1–3, 5, 9, and 10 was investigated using the agar diffusion method against fungi, Gram-positive and Gram-negative bacteria. In consequence, new compound 3 was found to possess the highest antibacterial activity against Enterococcus faecalis VRE and Mycobacterium vaccae. Cell proliferation and cytotoxicity tests were also applied on all isolated compounds and plant crude extract in vitro with the result of potent inhibitory effect against leukemia cells. In particular, the newly discovered isoflavone 10 was active against both of the leukemia cells K-562 and THP-1 while 4–6 of the flavanone type compounds were active against only THP-1. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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Review

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42 pages, 13195 KiB

Open AccessReview

Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review

by Gjoshe Stefkov, Ivana Cvetkovikj Karanfilova, Veronika Stoilkovska Gjorgievska, Ana Trajkovska, Nikola Geskovski, Marija Karapandzova and Svetlana Kulevanova

Molecules 2022, 27(3), 975; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030975 - 01 Feb 2022

Cited by 27 | Viewed by 6259

Abstract

Cannabis is gaining increasing attention due to the high pharmacological potential and updated legislation authorizing multiple uses. The development of time- and cost-efficient analytical methods is of crucial importance for phytocannabinoid profiling. This review aims to capture the versatility of analytical methods for [...] Read more.

Cannabis is gaining increasing attention due to the high pharmacological potential and updated legislation authorizing multiple uses. The development of time- and cost-efficient analytical methods is of crucial importance for phytocannabinoid profiling. This review aims to capture the versatility of analytical methods for phytocannabinoid profiling of cannabis and cannabis-based products in the past four decades (1980–2021). The thorough overview of more than 220 scientific papers reporting different analytical techniques for phytocannabinoid profiling points out their respective advantages and drawbacks in terms of their complexity, duration, selectivity, sensitivity and robustness for their specific application, along with the most widely used sample preparation strategies. In particular, chromatographic and spectroscopic methods, are presented and discussed. Acquired knowledge of phytocannabinoid profile became extremely relevant and further enhanced chemotaxonomic classification, cultivation set-ups examination, association of medical and adverse health effects with potency and/or interplay of certain phytocannabinoids and other active constituents, quality control (QC), and stability studies, as well as development and harmonization of global quality standards. Further improvement in phytocannabinoid profiling should be focused on untargeted analysis using orthogonal analytical methods, which, joined with cheminformatics approaches for compound identification and MSLs, would lead to the identification of a multitude of new phytocannabinoids. Full article

(This article belongs to the Special Issue Bioactive Compounds from Plants with Pharmaceutical Interest)

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