Protective Effects of Extracts, Isolated Compounds from <i>Desmodium uncinatum</i>and Semi-Synthetic Isovitexin Derivatives against Lipid Peroxidation of Hepatocyte’s Membranes  

作　　者：Borice T. Tsafack Cyrille L. K. Bomgning Jonas Kühlborn Romuald T. Fouedjou Beaudelaire K. Ponou Remy B. Teponno Agathe L. Fotio Luciano Barboni Till Opatz Télesphore B. Nguelefack Léon A. Tapondjou 

机构地区：[1]Research Unit of Applied and Environmental Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon [2]Research Unit of Animal Physiology and Phytopharmacology, Department of Animal Biology, Faculty of Science, University of Dschang, Dschang, Cameroon [3]Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Mainz, Germany [4]Department of Zoology and Animal Physiology, Faculty of Science, University of Buea, Buea, Cameroon [5]School of Science and Technology, Chemistry Division, University of Camerino, Camerino, Italy

出　　处：《Advances in Biological Chemistry》2018年第6期101-120,共20页生物化学进展（英文）

摘　　要：Lipid peroxidation plays a pivotal role in the pathogenicity and maintenance of hepatitis. Thus, substances protecting hepatocyte membranes from lipid peroxidation are of great importance in the management of hepatotoxicity and hepatitis. The present work deals with the in vitro hepatoprotective activity of the methanol extract of Desmodium uncinatum, its sub-fractions, the major isolated compounds and some of their semi-synthetic derivatives in order to study structure activity relationships. Using hydrogen peroxide (H2O2)-induced lipid peroxidation of hepatocyte membranes as a model, the hepatoprotective-guided phytochemical survey of the methanol extract of aerial parts of D. uncinatum was carried out by successive column chromatography. One of the most active compounds (Isovitexin) was chemically transformed to yield new semi-synthetic. The identification of isolated and semi-synthetic compounds was performed using NMR techniques, mass spectrometry and by comparison of their data with those reported in the literature. The n-butanol fraction was the most effective (IC50: 22.9 μg/mL) compared to the crude methanol extract (IC50: 43.6 μg/mL) and other fractions. The n-butanol sub-fractions FA (containing non-phenolic compounds) and FB (mainly containing phenolic compounds) exhibited respective IC50 of 14.36 and 128.2 μg/ml. Purification of FA yielded 3-O-β-D-glucopyranosyl-β-sitosterol (1), 3-O-β-D- 2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (2), (2S, 3S, 4R, 7R, 8Z)-1-O-β-D-glucopyranosyl-2-[(R)-2'-hydroxyarachidoylamino]-docosan-8-ene-3,4,7-triol (4), spiraeamide (5), mannitol (6), while FB afforded essentially three C-glycosylflavonoids namely isovitexin (7), vitexin (8) and vicenin-3 (9). Chemical transformations (methylation, allylation and prenylation) of isovitexin afforded five new semi-synthetic derivatives: 4',5,7-O- trimethyli-sovitexin (10), 4'-O-allylisovitexin (11), 4',7-O-diallylisovitexin (12), 4'-O-prenylisovitexin (13) and 8-C-prenyl-4',7-O-diprenylisovitexin (14). The screening oLipid peroxidation plays a pivotal role in the pathogenicity and maintenance of hepatitis. Thus, substances protecting hepatocyte membranes from lipid peroxidation are of great importance in the management of hepatotoxicity and hepatitis. The present work deals with the in vitro hepatoprotective activity of the methanol extract of Desmodium uncinatum, its sub-fractions, the major isolated compounds and some of their semi-synthetic derivatives in order to study structure activity relationships. Using hydrogen peroxide (H2O2)-induced lipid peroxidation of hepatocyte membranes as a model, the hepatoprotective-guided phytochemical survey of the methanol extract of aerial parts of D. uncinatum was carried out by successive column chromatography. One of the most active compounds (Isovitexin) was chemically transformed to yield new semi-synthetic. The identification of isolated and semi-synthetic compounds was performed using NMR techniques, mass spectrometry and by comparison of their data with those reported in the literature. The n-butanol fraction was the most effective (IC50: 22.9 μg/mL) compared to the crude methanol extract (IC50: 43.6 μg/mL) and other fractions. The n-butanol sub-fractions FA (containing non-phenolic compounds) and FB (mainly containing phenolic compounds) exhibited respective IC50 of 14.36 and 128.2 μg/ml. Purification of FA yielded 3-O-β-D-glucopyranosyl-β-sitosterol (1), 3-O-β-D- 2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (2), (2S, 3S, 4R, 7R, 8Z)-1-O-β-D-glucopyranosyl-2-[(R)-2'-hydroxyarachidoylamino]-docosan-8-ene-3,4,7-triol (4), spiraeamide (5), mannitol (6), while FB afforded essentially three C-glycosylflavonoids namely isovitexin (7), vitexin (8) and vicenin-3 (9). Chemical transformations (methylation, allylation and prenylation) of isovitexin afforded five new semi-synthetic derivatives: 4',5,7-O- trimethyli-sovitexin (10), 4'-O-allylisovitexin (11), 4',7-O-diallylisovitexin (12), 4'-O-prenylisovitexin (13) and 8-C-prenyl-4',7-O-diprenylisovitexin (14). The screening o

关 键 词：DESMODIUM uncinatum HEPATOPROTECTIVE Activity Lipid PEROXIDATION HEPATOCYTE Membranes C-glycosylflavonoids 

分 类 号：R28[医药卫生—中药学]