Four cycloartane triterpenoids and six related saponins from Passiflora edulis.
Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and 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 Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A-D were assigned as 22(R), 24(S)-1alpha,3beta,22,24,31-pentahydroxy-24-methylcycloartan -28-oic acid; 24(S)-1alpha,3beta,24, 31-tetrahydroxy-24-methylcycloartan-28-oic acid; 20(S),24(S)-1alpha, 3beta,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1alpha,3beta,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were established as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Finally, cyclopassiflosides III and V were demonstrated as the 28, 31-bis-O-beta-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).
Yoshikawa
K
K
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-Cho, Tokushima 770-8514, Japan. yosikawa@ph.bunri-u.ac.jp
Katsuta
S
S
Mizumori
J
J
Arihara
S
S
D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D019685:Rosales / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D013057:Spectrum Analysis; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
D012503:Saponins; D014315:Triterpenes