title: Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules.
abstract: 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 (1)H-NMR, (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 muM (P<0.05). 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.
authors: Faculty of Human Wellness, Tokaigakuen University, Nagoya, Japan. miyakeyo@tokaigakuen-u.ac.jp
authors: Yoshiaki
authors: Y
authors: Miyake
authors: Mika
authors: M
authors: Mochizuki
authors: Miki
authors: M
authors: Okada
authors: Masanori
authors: M
authors: Hiramitsu
authors: Yasujiro
authors: Y
authors: Morimitsu
authors: Toshihiko
authors: T
authors: Osawa
mesh_terms: D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D015815:Cell Adhesion Molecules / Q000235:genetics*; D002478:Cells, Cultured; D002957:Citrus / Q000737:chemistry*; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000302:isolation & purification; D005786:Gene Expression Regulation / Q000187:drug effects*; D005960:Glucosides / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology; D008517:Phytotherapy; D014471:Umbilical Veins / Q000166:cytology
chemical_list: D000975:Antioxidants; D015815:Cell Adhesion Molecules; D016166:Free Radical Scavengers; D005960:Glucosides; D010636:Phenols