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1. (Article ID: 12458)
 
Matsuda H, Kageura T, Inoue Y, Morikawa T, Yoshikawa M
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
Tetrahedron 56(39) (2000) 7763-7777
 

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-β-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 α-methylene-γ-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.

Saussurea lappa, saussureamines, gastroprotective effect, (-)-massoniresinol glucoside

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