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.
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页码：7763 / 7777
页数：15
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