New guaianolides and xanthine oxidase inhibitory flavonols from ajania fruticulosa

Two new guaianolides (1 and 2) were isolated from the aerial parts of Ajania fruticulosa along with a triterpene (alpha-amyrin), two plant sterols (beta-sitosterol and daucosterol), four flavonols [santin (3), axillarin (4), centaureidin, and 5,7,4'-trihydroxy-3, 3'-dimethoxyflavone], and five sesquiterpenes [ketoplenolide B, 9beta-hydroxyeudesma-4,11(13)-dien-12-oic acid, 9beta-acetoxyeudesma-4,11(13)-dien-12-oic acid, 1alpha,4alpha, 10alpha-trihydroxy-9alpha-angeloyloxyguaia-2,11(13)-dien-12, 6alpha-olide, and 3beta,4alpha-dihydroxyguaia-11(13),10(14)-dien-12, 6alpha-olide]. The structures of the new guaianolides were established as 1alpha-hydroperoxy-4beta,8alpha,10alpha, 13-tetrahydroxyguaia-2-en-12,6alpha-olide (1) and 1alpha-hydroperoxy-4alpha, 10alpha-dihydroxy-9alpha-angeloyloxyguaia-2,11(13)-dien-12, 6alpha-olide (2), respectively. Xanthine oxidase assays of all isolates revealed that santin (3) and axillarin (4) inhibited the enzyme with IC(50) values of 36.5 and 36.0 &mgr;M (that of allopurinol used as a positive control in the study was 24.2 &mgr;M), respectively.