Antioxidative activities of galloyl glucopyranosides from the stem-bark of Juglans mandshurica

• Published in: Bioscience, biotechnology, and biochemistry Vol. 72; no. 8; pp. 2158 - 2163
• Main Authors: Ngoc, T.M.(Chungnam National Univ., Daejon (Korea R.)), Hung, T.M, Thuong, P.T, Kim, J.C, Choi, J.S, Bae, K.H, Hattori, M, Choi, C.S, Lee, J.S, Min, B.S
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.08.2008; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: 1,2,3,6-tetragalloylglucose; 1,2,6-trigalloylglucose; ANTIOXIDANTES; ANTIOXIDANTS; Antioxidants - chemistry; Antioxidants - pharmacology; antioxidative activity; ANTIOXYDANT; Biological and medical sciences; COMPOSE PHENOLIQUE; COMPUESTOS FENOLICOS; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; ESPECIES DE OXIGENO REACTIVO; FREE RADICALS; Fundamental and applied biological sciences. Psychology; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - pharmacology; Glycine max - enzymology; Humans; Jugland mandshurica; Juglandaceae; JUGLANS; Juglans - chemistry; LIPID PEROXIDATION; Lipid Peroxidation - drug effects; LIPOXIGENASA; LIPOXYGENASE; Lipoxygenase - metabolism; Molecular Structure; PEROXIDACION LIPIDICA; PEROXYDATION DES LIPIDES; PHENOLIC COMPOUNDS; Plant Bark - chemistry; RADICAL LIBRE; RADICALES LIBRES; REACTIVE OXYGEN SPECIES; Substrate Specificity; XANTHINE; Xanthine Oxidase - antagonists & inhibitors; Xanthine Oxidase - metabolism; XANTHINES; XANTINAS; Juglandaceae; Juglans; Dicotyledones; Angiospermae; 1,2,3,6-tetragalloylglucose; 1,2,6- trigalloylglucose; Spermatophyta; antioxidative activity; Antioxidant; Jugland mandshurica
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.80222

Two phenolics, 1,2,6-trigalloylglucose (1) and 1,2,3,6-tetragalloylglucose (2), isolated from the stem-bark of Juglans mandshurica were evaluated for their antioxidative activities. The results showed that compounds 1 and 2 exhibited strong scavenging activities against 1,1'-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-(3-ethylbenzenthiazoline-6-sulphonic) acid (ABTSsup(+)radical), and superoxide radicals (O2sup(-)radical), and also had a significant inhibitory effect on lipid peroxidation and low-density lipoprotein (LDL) oxidation. The strong superoxide radical scavenging of 1 and 2 resulted from the potential competitive inhibition with xanthine at the active site of xanthine oxidase (OX). In addition, compounds 1 and 2 displayed significant lipoxygenase inhibitory activity, the mode of inhibition also being identified as competitive. In comparison, the antioxidative activities of compounds 1 and 2, together with gallic acid, indicated that the number of galloyl moieties could play an important role in the antioxidative activity.