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Keywords = β-glucogallin

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16 pages, 644 KB  
Article
Isolation and Identification of Secondary Metabolites in Rheum tataricum L.fil. Growing in Kazakhstan and Surveying of Its Anticancer Potential
by Aiman A. Turgunbayeva, Nurgul A. Sultanova, Mohammad Saleh Hamad, Victor A. Savelyev, Elena I. Chernyak, Irina Yu. Bagryanskaya, Mikhail A. Pokrovsky, Andrey G. Pokrovsky, Nadezhda G. Gemejiyeva and Elvira E. Shults
Molecules 2025, 30(14), 2978; https://doi.org/10.3390/molecules30142978 - 15 Jul 2025
Viewed by 572
Abstract
Rheum tataricum L.fil., known for its high tolerance to drought, salinity, and nutritional deficiency, is the least studied species of wild rhubarb. Extract of roots and rhizomes of R. tataricum has been traditionally used for the treatment of different diseases such as liver, [...] Read more.
Rheum tataricum L.fil., known for its high tolerance to drought, salinity, and nutritional deficiency, is the least studied species of wild rhubarb. Extract of roots and rhizomes of R. tataricum has been traditionally used for the treatment of different diseases such as liver, kidney, womb, and bladder diseases and also relapsing fever. An ethanol extract of the roots of R. tataricum was prepared and further successively fractionated by extraction with tert-butyl methyl ether (TBME) and ethyl acetate (EtOAc). The obtained extract fractions were subjected to a series of chromatographic separations on silica gel for the isolation of its individual compounds. A total of 12 individual compounds, 2-O-β-D-glucopyranoside of R-(4-hydroxyphenyl)-2-butanol (rhododendrin) 1, gallic acid 2, 2-O-β-D-glucopyranoside of S-4-(4-hydroxyphenyl)-2-butanol (epi-rhododendrin) 3, their aglycones (-)-(2R)-rhododendrol 4 and (+)-(2S)-rhododendrol 5, gallotannin β-glucogallin 6, chlorogenic acids (3,5-di-O-caffeoylquinic acid 7 and 5-O-caffeoyl-3-O-(p-coumaroyl) quinic acid 8), 4-(4-hydroxyphenyl)-2-butanon (raspberry ketone) 9 and three stilbenes (rhaponticin 10, desoxyrhaponticin 11 and resveratroloside 12), were isolated and characterized. The structure of desoxyrhaponticin 11 was confirmed by X-ray diffraction analyses. The results of in vitro biological assays (the MTT test) showed that ethanol extract Rheum tataricum was non-toxic against the normal epithelial VERO cells. The isolated compounds 1, 4, 11 and 12 exhibited cytotoxicity against a cervical cancer cell line (CaSki), breast adenocarcinoma (MCF7) and glioblastoma cell line (SNB-19) at low micromolar concentrations. Polyhydroxystilbenes 11 and 12 showed the best potency against adenocarcinoma cells (GI50 = 7–8 μM). The inhibition activity towards cancer cells was comparable to those of the standard drug doxorubicin. The available from R. tataricum secondary metabolites may serve as new leads for the discovery of anticancer drugs. Full article
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24 pages, 3802 KB  
Review
Super Fruit Amla (Emblica officinalis, Gaertn) in Diabetes Management and Ensuing Complications: A Concise Review
by Muhammed Majeed, Narayanan K. Narayanan, Lakshmi Mundkur, Priji Prakasan and Kalyanam Nagabhushanam
Nutraceuticals 2023, 3(3), 329-352; https://doi.org/10.3390/nutraceuticals3030026 - 7 Jul 2023
Cited by 10 | Viewed by 18295
Abstract
Type 2 diabetes mellitus (T2DM) is a chronic metabolic disease showing an exponential increase in its prevalence all over the world. High blood glucose level is one of the main clinical signs of the disease. Although several classes of drugs are available for [...] Read more.
Type 2 diabetes mellitus (T2DM) is a chronic metabolic disease showing an exponential increase in its prevalence all over the world. High blood glucose level is one of the main clinical signs of the disease. Although several classes of drugs are available for treatment, their prolonged use and adverse effects behoove the use of alternative medicine. Plant-derived natural products have multifaceted beneficial roles in human pathophysiology. Plant metabolites like tannins, organic acids, polyphenols, terpenes, and flavonoids show multiple mechanisms of action against diabetes. The fruits of Emblica officinalis (EOF), also known as Indian gooseberry (amla), contain several phytochemicals, potentially having anti-diabetic activity. Hydrolyzable tannins are the major bioactive components of the amla fruit, the most abundant hydrolyzable tannin being β-glucogallin. The present review summarizes the mechanism of action and clinical evidence for the beneficial effects of EOF on T2DM and its associated complications. Full article
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15 pages, 744 KB  
Article
Phenolics Profiling by HPLC-DAD-ESI/MSn of the Scientific Unknown Polygonum hydropiperoides Michx. and Its Antioxidant and Anti-Methicillin-Resistant Staphylococcus aureus Activities
by Ygor Ferreira Garcia da Costa, Eulogio José Llorent-Martínez, Laura Silva Fernandes, Pedro Henrique Santos de Freitas, Elita Scio, Orlando Vieira de Sousa, Paula Cristina Castilho and Maria Silvana Alves
Plants 2023, 12(8), 1606; https://doi.org/10.3390/plants12081606 - 10 Apr 2023
Cited by 5 | Viewed by 2394
Abstract
Polygonum hydropiperoides Michx. is an Asian native plant species that is also widely distributed in the Americas. Despite its traditional uses, P. hydropiperoides is scarcely scientifically exploited. This study aimed to chemically characterize and investigate the antioxidant and antibacterial activities of hexane (HE-Ph), [...] Read more.
Polygonum hydropiperoides Michx. is an Asian native plant species that is also widely distributed in the Americas. Despite its traditional uses, P. hydropiperoides is scarcely scientifically exploited. This study aimed to chemically characterize and investigate the antioxidant and antibacterial activities of hexane (HE-Ph), ethyl acetate (EAE-Ph), and ethanolic (EE-Ph) extracts from aerial parts of P. hydropiperoides. The chemical characterization was performed through HPLC-DAD-ESI/MSn. The antioxidant activity was assessed by the phosphomolybdenum reducing power, nitric oxide inhibition, and the β-carotene bleaching assays. The antibacterial activity was determined by the minimal inhibitory concentration (MIC) and the minimal bactericidal concentration followed by the classification of the antibacterial effect. Chemical characterization revealed the expressive presence of phenolic acids and flavonoids in EAE-Ph. An increased antioxidant capacity was revealed in EAE-Ph. Regarding antibacterial activity, EAE-Ph showed weak to moderate property against 13 strains tested with MIC values ranging from 625 to 5000 µg/mL, with bactericidal or bacteriostatic effects. Glucogallin and gallic acid stand out as the most relevant bioactive compounds. These results suggest that P. hydropiperoides is a natural source of active substances, supporting this species’ traditional use. Full article
(This article belongs to the Section Phytochemistry)
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32 pages, 7122 KB  
Article
Glucogallin Attenuates the LPS-Induced Signaling in Macrophages and Protects Mice against Sepsis
by Rajveer Singh, Shivani Chandel, Arijit Ghosh, Tushar Matta, Anupam Gautam, Arka Bhattacharya, Srivalliputturu Sarath Babu, Soumi Sukla, Debasish Nag, Velayutham Ravichandiran, Syamal Roy and Dipanjan Ghosh
Int. J. Mol. Sci. 2022, 23(19), 11254; https://doi.org/10.3390/ijms231911254 - 24 Sep 2022
Cited by 16 | Viewed by 4886
Abstract
The anti-oxidant and anti-inflammatory effect of beta-glucogallin (BGG), a plant-derived natural product, was evaluated in both in vitro and in vivo studies. For the in vitro study, the ability of BGG pre-treatment to quench LPS-induced effects compared to LPS alone in macrophages was [...] Read more.
The anti-oxidant and anti-inflammatory effect of beta-glucogallin (BGG), a plant-derived natural product, was evaluated in both in vitro and in vivo studies. For the in vitro study, the ability of BGG pre-treatment to quench LPS-induced effects compared to LPS alone in macrophages was investigated. It was found that BGG pre-treatment showed a significant decrease in ROS, NO, superoxide, and pro-inflammatory cytokines (TNF-alpha, IL-4, IL-17, IL-1β, and IL-6) and increased reduced glutathione coupled with the restoration of mitochondrial membrane potential. Gene profiling and further validation by qPCR showed that BGG pre-treatment downregulated the LPS-induced expression of c-Fos, Fas, MMP-9, iNOS, COX-2, MyD88, TRIF, TRAF6, TRAM, c-JUN, and NF-κB. We observed that BGG pre-treatment reduced nuclear translocation of LPS-activated NF-κB and thus reduced the subsequent expressions of NLRP3 and IL-1β, indicating the ability of BGG to inhibit inflammasome formation. Molecular docking studies showed that BGG could bind at the active site of TLR4. Finally, in the LPS-driven sepsis mouse model, we showed that pre-treatment with BGG sustained toxic shock, as evident from their 100% survival. Our study clearly showed the therapeutic potential of BGG in toxic shock syndrome. Full article
(This article belongs to the Special Issue Natural Compounds for Inflammation and Anti-inflammatory Mechanism)
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13 pages, 2994 KB  
Article
Glucogallin Attenuates RAW 264.7 Cells from Arsenic Trioxide Induced Toxicity via the NF-ҡB/NLRP3 Pathway
by Anam Najib Khan, Rajveer Singh, Arka Bhattacharya, Sonu Kumar, Arijit Ghosh, Debasish Nag, Velayutham Ravichandiran and Dipanjan Ghosh
Molecules 2022, 27(16), 5263; https://doi.org/10.3390/molecules27165263 - 18 Aug 2022
Cited by 9 | Viewed by 3706
Abstract
Chronic arsenic (As) poisoning is mostly due to subsoil water contaminated with As and its salts. Exposure to As has been found to cause an elevation in reactive oxygen species (ROS), leading to the damage of DNA and proteins, and it also causes [...] Read more.
Chronic arsenic (As) poisoning is mostly due to subsoil water contaminated with As and its salts. Exposure to As has been found to cause an elevation in reactive oxygen species (ROS), leading to the damage of DNA and proteins, and it also causes immunotoxicity. Treatment regimens are primarily based on chelation therapy and amino acid and vitamin supplementations. Recent studies have established that natural products display effective and progressive relief from arsenicosis without any side effects. β-glucogallin (BGG), a gallo-tannin natural product, is reported to possess anti-oxidant and anti-inflammatory properties. In the present study, we aim to observe the protective role of BGG against As-induced cytotoxicity, apoptosis, mitochondrial dysfunction, and the underlying mechanisms in RAW 264.7 macrophage cells. We found that BGG alleviates As-induced ROS, apoptosis, and mitochondrial dysfunction in RAW 264.7 macrophage cells. Thus, BGG can be used therapeutically to prevent As-induced toxicity. Full article
(This article belongs to the Special Issue Natural Antioxidants Are Associated with ROS and Diseases)
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20 pages, 4693 KB  
Article
Identification and Characterization of Glucosyltransferase That Forms 1-Galloyl-β-d-Glucogallin in Canarium album L., a Functional Fruit Rich in Hydrolysable Tannins
by Qinghua Ye, Shiyan Zhang, Nana Qiu, Linmin Liu, Wei Wang, Qian Xie, Qiang Chang and Qingxi Chen
Molecules 2021, 26(15), 4650; https://doi.org/10.3390/molecules26154650 - 31 Jul 2021
Cited by 15 | Viewed by 3725
Abstract
Hydrolysable tannins (HTs) are useful secondary metabolites that are responsible for pharmacological activities and astringent taste, flavor, and quality in fruits. They are also the main polyphenols in Canarium album L. (Chinese olive) fruit, an interesting and functional fruit that has been cultivated [...] Read more.
Hydrolysable tannins (HTs) are useful secondary metabolites that are responsible for pharmacological activities and astringent taste, flavor, and quality in fruits. They are also the main polyphenols in Canarium album L. (Chinese olive) fruit, an interesting and functional fruit that has been cultivated for over 2000 years. The HT content of C. album fruit was 2.3–13 times higher than that of berries with a higher content of HT. 1-galloyl-β-d-glucose (βG) is the first intermediate and the key metabolite in the HT biosynthesis pathway. It is catalyzed by UDP-glucosyltransferases (UGTs), which are responsible for the glycosylation of gallic acid (GA) to form βG. Here, we first reported 140 UGTs in C. album. Phylogenetic analysis clustered them into 14 phylogenetic groups (A, B, D–M, P, and Q), which are different from the 14 typical major groups (A~N) of Arabidopsis thaliana. Expression pattern and correlation analysis showed that UGT84A77 (Isoform0117852) was highly expressed and had a positive correlation with GA and βG content. Prokaryotic expression showed that UGT84A77 could catalyze GA to form βG. These results provide a theoretical basis on UGTs in C. album, which will be helpful for further functional research and availability on HTs and polyphenols. Full article
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