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)-1α,3β,22,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; 24(S)-1α,3β,24,31-tetrahydroxy-24-methylcycloartan-28-oic acid; 20(S),24(S)-1α,3β,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1α,3β,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I−VI, in turn, were established as the 28-O-β-d-glucopyranosides of cyclopassifloic acids A−D. Finally, cyclopassiflosides III and V were demonstrated as the 28,31-bis-O-β-d-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).
saponins, Passiflora edulis, cycloartane triterpenes, cyclopassifloic acids A-D
NCBI PubMed ID: 11000025Publication DOI: 10.1021/np000126+Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: yosikawa@ph.bunri-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, HPLC, extraction, CC
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