Anti-inflammatory tetramers of resveratrol from the roots of Vitis amurensis and the conformations of the seven-membered ring in some oligostilbenes.
Five resveratrol tetramers, amurensins I-M, were isolated from the roots of Vitis amurensis (Rupr.), together with five known resveratrol tetramers, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A, and heyneanol A. Their structures and stereochemistry were determined by chemical and spectroscopic methods, especially by use of 2D NMR analysis. Some of them had an ampelopsin A or a balanocarpol unit, in which the conformations of the seven-membered carbon ring were described for the first time. The anti-inflammatory activities of the tetramers were also tested. Among them, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A and heyneanol A showed potent inhibition on the biosynthesis of leukotriene B4 (LTB4), and amurensins I and L showed strong antagonism of the histamine acceptor.
Huang
K S
KS
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, People's Republic of China.
Lin
M
M
Cheng
G F
GF
D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001704:Biopolymers; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D000077185:Resveratrol; D013057:Spectrum Analysis; D013267:Stilbenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D027843:Vitis / Q000737:chemistry*
D000893:Anti-Inflammatory Agents; D001704:Biopolymers; D013267:Stilbenes; D000077185:Resveratrol