Isolation of antioxidative phenolic glucosides from lemon [Citrus limon] juice and their suppressive effect on the expression of blood adhesion molecules

• Published in: Bioscience, biotechnology, and biochemistry Vol. 71; no. 8; pp. 1911 - 1919
• Main Authors: Miyake, Y.(Tokaigakuen Univ., Nagoya (Japan)), Mochizuki, M, Okada, M, Hiramitsu, M, Morimitsu, Y, Osawa, T
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.08.2007; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: antioxidant; ANTIOXIDANTES; ANTIOXIDANTS; Antioxidants - isolation & purification; Antioxidants - pharmacology; ANTIOXYDANT; Biological and medical sciences; Cell Adhesion Molecules - genetics; Cells, Cultured; Citrus - chemistry; CITRUS LIMON; COMPOSE PHENOLIQUE; COMPUESTOS FENOLICOS; Endothelial Cells - cytology; Endothelial Cells - drug effects; Endothelial Cells - metabolism; Free Radical Scavengers - isolation & purification; FRUIT JUICES; Fundamental and applied biological sciences. Psychology; Gene Expression Regulation - drug effects; GLUCOSIDE; GLUCOSIDES; Glucosides - isolation & purification; Glucosides - pharmacology; GLUCOSIDOS; Humans; intercellular adhesion molecule-1 (ICAM-1); JUGO DE FRUTAS; JUS DE FRUITS; lemon juice; Magnetic Resonance Spectroscopy; Mass Spectrometry; PHENOLIC COMPOUNDS; phenolic glucoside; Phenols - isolation & purification; Phenols - pharmacology; Phytotherapy; Umbilical Veins - cytology; phenolic glucoside; Glucoside; Cell adhesion molecule; Phenols; Isolation; intercellular adhesion molecule-1 (ICAM-1); Antioxidant; lemon juice; Adhesion; Blood
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.70115

Phenolic glucosides having radical scavenging activity were examined from the fraction eluted with 20% methanol on Amberlite XAD-2 resin applied to lemon (Citrus limon) juice by using reversed phase chromatography. Four phenolic glucosides were identified as 1-feruloyl-beta-D-glucopyranoside, 1-sinapoyl-beta-D-glucopyranoside, 6,8-di-C-glucosylapigenin and 6,8-di-C-glucosyldiosmetin by sup(1)H-NMR, sup(13)C-NMR, and MS analyses. They exhibited radical scavenging activity for 1,1-diphenyl-2-picrylhydrazyl(DPPH) and superoxide, although the activity was low in comparison with eriocitrin, a potent antioxidant in lemon fruit, and the eriodictyol of its aglycone. The phenolic compounds in lemon juice were examined for their suppressive effect on the expression of blood adhesion molecules by measuring the expression of intercellular adhesion molecule-1 (ICAM-1) in human umbilical vein endothelial cells (HUVECs) induced by necrosis factor-alpha (TNF-alpha). 6,8-Di-C-glucosylapigenin, apigenin, and diosmentin of the flavones were found to significantly suppress the expression of ICAM-1 at 10 microM (P0.05). The phenolic glucosides isolated in this study were contained in comparative abundance in daidai (Citrus aurantium) and niihime (Citrus unshiu x Citrus tachibana) among the sour citrus juices.