Biflavonoids and a glucopyranoside derivative from Ouratea semiserrata.

Two new biflavonoids, 5-hydroxy-7-methoxyflavone-(4' --> O --> 8")-4"',5",7"-trihydroxyflavone and 5-hydroxy-7-methoxyflavone-(4' --> O --> 8")-5",7"-dihydroxy-4"'-methoxyflavone, and the glucopyranoside derivative, 1-O-(4-hydroxyphenyl)-6-O-(4-hydroxybenzoyl)-beta-D-glucopyranoside, as well as the known biflavones lanaraflavone, amentoflavone and podocarpusflavone, the triterpenes lupeol and friedelin, the lignans eudesmin and epieudesmin, the flavonol glycoside rutin, the steroids beta-sitosterol, stigmasterol, 3beta-O-beta-D-glucopyranosylsitosterol, 7-oxostigmast-5-en-3beta-ol and 7-oxostigmasta-5,22-dien-3beta-ol, the carbohydrates alpha- and beta-glucopyranose and 1-O-(4-hydroxybenzoyl)-beta-D-glucopyranoside, and the norsesquiterpene 6,9-dihydroxymegastigma-4,7-dien-3-one, have been isolated from leaves and branches of Ouratea semiserrata. The structures of these compounds were established from spectral data, including two-dimensional NMR experiments and mass spectra.