Tissue factor inhibitory flavonoids from the fruits of Chaenomeles sinensis.
Tissue factor (TF, tissue thromboplastin or coagulation factor III) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification utilizing a bio-assay method of prothrombin time prolongation, was carried out to yield five active flavoniods such as hovetrichoside C (1) (IC50 = 14.0 microg), luteolin-7-O-beta-D-glucuronide (3) (IC50 = 31.9 microg), hyperin (4) (IC50 = 20.8 microg), avicularin (6) (IC50 = 54.8 microg) and quercitrin (10) (IC50 = 135.7 microg), along with other inactive compounds such as (+/-)-(2E,4E-O-beta-D-glucopyranosyl-4'-hydroxy-beta-ionylideneacetic acid ester (2), genistein-7-O-beta-D-glucopyranoside (5), luteolin-3'-methoxy-4'-O-beta-D-glucopyranoside (7), luteolin-7-O-beta-D-glucuronide methyl ester (8), tricetin-3'-methoxy-4'-O-beta-D-glucopyranoside (selagin-4'-O-beta-D-glucopyranoside) (9), (-)-epicatechin (11), luteolin-4'-O-beta-D-glucopyranoside (12) and apigenin-7-O-beta-D-glucuronide methyl ester (13). The structures of the isolated compounds were elucidated through spectral analysis. Among them, compounds 1 to 9,12 and 13 were isolated for the first time from the fruits of this plant and the compound 9 is a new flavonoid.
Lee
Ming Hong
MH
Natural Products Research Institute, Seoul National University, Seoul 110-460, Korea.
Son
Yeon Kyoung
YK
Han
Yong Nam
YN
D000818:Animals; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry*; D008861:Microsomes / Q000187:drug effects / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D027824:Rosaceae / Q000737:chemistry*; D013925:Thromboplastin / Q000037:antagonists & inhibitors* / Q000378:metabolism
D005419:Flavonoids; D010936:Plant Extracts; D013925:Thromboplastin