Synthesis of oligosaccharides of genistein and quercetin as potential anti-inflammatory agents

被引:17
作者
Shimoda, Kei [1 ]
Kobayashi, Tatsunari [2 ]
Akagi, Masaaki [3 ]
Hamada, Hatsuyuki [4 ]
Hamada, Hiroki [2 ]
机构
[1] Oita Univ, Fac Med, Dept Pharmacol & Therapeut, Oita 8795593, Japan
[2] Okayama Univ Sci, Fac Sci, Dept Life Sci, Okayama 7000005, Japan
[3] Tokushima Bunri Univ, Fac Pharmaceut Sci, Dept Pharmacol, Yamashiro, Tokushima 7708514, Japan
[4] Natl Inst Fitness & Sports Kanoya, Kagoshima 8912390, Japan
关键词
D O I
10.1246/cl.2008.876
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Genistein was glucosylated to its 7-O-beta-D-glucoside by cultured cells of Ipomoea batatas, while Cultured Marchantia polymorpha cells produced 4'-O-beta-D-glucoside and 7-O-beta-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-beta-D-glucoside by I. batatas, and M. polymorpha gave 3-O-beta-D-glucoside and 7-O-beta-D-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding beta-maltosides and beta-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-beta-maltooligosaccharides, quercetin 3-O-beta-glucoside. and quercetin 7-O-beta-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.
引用
收藏
页码:876 / 877
页数:2
相关论文
共 8 条
[1]  
AKAGI M, 1994, BIOL PHARM BULL, V17, P732
[2]   The quercetin paradox [J].
Boots, Agnes W. ;
Li, Hui ;
Schins, Roel P. F. ;
Duffin, Rodger ;
Heemskerk, Johan W. M. ;
Bast, Aalt ;
Haenen, Guido R. M. M. .
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2007, 222 (01) :89-96
[3]   ABSORPTION OF DIETARY QUERCETIN GLYCOSIDES AND QUERCETIN IN HEALTHY ILEOSTOMY VOLUNTEERS [J].
HOLLMAN, PCH ;
DEVRIES, JHM ;
VANLEEUWEN, SD ;
MENGELERS, MJB ;
KATAN, MB .
AMERICAN JOURNAL OF CLINICAL NUTRITION, 1995, 62 (06) :1276-1282
[4]   Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus [J].
Kaminaga, Y ;
Nagatsu, A ;
Akiyama, T ;
Sugimoto, N ;
Yamazaki, T ;
Maitani, T ;
Mizukami, H .
FEBS LETTERS, 2003, 555 (02) :311-316
[5]   Synthesis of unnatural mono- and oligosaccharides of farnesol, geraniol, and (S)-Perillyl alcohol by biocatalytic glycosylations [J].
Shimoda, Kei ;
Sakamoto, Sou ;
Nakajima, Nobuyoshi ;
Hamada, Hatsuyuki ;
Hamada, Hiroki .
CHEMISTRY LETTERS, 2008, 37 (05) :556-557
[6]   Glycosylation and malonylation of quercetin, epicatechin, and catechin by cultured plant cells [J].
Shimoda, Kei ;
Otsuka, Takanao ;
Morimoto, Yoko ;
Hamada, Hatsuyuki ;
Hamada, Hiroki .
CHEMISTRY LETTERS, 2007, 36 (10) :1292-1293
[7]   Synthesis of α-tocopheryl disaccharides as potential antiallergic agents [J].
Shimoda, Kei ;
Kondo, Yoko ;
Akagi, Masaaki ;
Abe, Koichi ;
Hamada, Hatsuyuki ;
Hamada, Hiroki .
CHEMISTRY LETTERS, 2007, 36 (04) :570-571
[8]   Distinctive antioxidant and antiinflammatory effects of flavonols [J].
Wang, Lisu ;
Tu, Yi-Chen ;
Lian, Tzi-Wei ;
Hung, Jing-Ting ;
Yen, Jui-Hung ;
Wu, Ming-Jiuan .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (26) :9798-9804