Four cycloartane triterpenoids and six related saponins from Passiflora edulis

Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), an d D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7 ), IV (8), V (9), and VI (10), were isolated from the leaves and stems of P assiflora edulis, and their structures were elucidated on the base of exten sive NMR experiments and chemical methods. Cyclopassifloic acids A-D were a ssigned as 22(R),24(S)-1 alpha,3 beta,22,24,31-pentahydroxy-24-methylcycloa rtan-28-oic acid; 24(5)-1 alpha,3 beta,24,31-tetrahydroxy-24-methycycloarta n-28-oic acid; 20(S),24(S)-1 alpha,3 beta,21,24,31-pentahydroxy-24-methylcy cloartan-28-oic acid; and 22(R)-1 alpha,3 beta,22-trihydroxy-24-oxocycloart an-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were establ ished as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Fin ally, cyclopassiflosides III and V were demonstrated as the 28,31-bis-O-bet a-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also o btained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).