Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa

被引：89

作者：

Matsuda, H ^{[1
]}

Kageura, T ^{[1
]}

Inoue, Y ^{[1
]}

Morikawa, T ^{[1
]}

Yoshikawa, M ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 39期

关键词：

amino acids and derivatives; Michael reactions; pharmacologically active compounds; terpenes and terpenoids;

D O I：

10.1016/S0040-4020(00)00696-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

From the methanolic extract of the dried roots of Saussurea lappa Clarke, Saussureae Radix, five amino acid-sesquiterpene conjugates, saussureamines A, B, C, D and E, were isolated together with a lignan glycoside, (-)-massoniresinol 4 "-O-beta-D-glucopyranoside. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, saussureamines and the related amino acid-sesquiterpene conjugates were synthesized using a Michael type addition reaction of amino acid to the alpha-methylene-gamma-lactone moiety of sesquiterpenes. Saussureamines A, B and C, costunolide and dehydrocostus lactone showed a gastroprotective effect on acidified ethanol-induced gastric mucosal lesions in rats. Saussureamines A also exhibited an inhibitory effect on gastric mucosal lesions induced by water-immersion stress in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7763 / 7777

页数：15

共 25 条

[1] TERPENOIDS .68. STRUCTURE AND ABSOLUTE CONFIGURATION OF COSTIC ACID-A NEW SESQUITERPENIC ACID FROM COSTUS ROOT OIL [J].