Two new cycloartane-type triterpenoids and one new flavanone from the leaves of Dasymaschalon dasymaschalum and their biological activity

• Published in: Phytochemistry letters 2013-05, Vol.6 (2), p.286-290
• Main Authors: Prawat, Uma, Chairerk, Orapan, Lenthas, Ratchanee, Salae, Abdul-Wahab, Tuntiwachwuttikul, Pittaya
• Format: Article
• Language: English
• Subjects: antibacterial properties; anticarcinogenic activity; antimalarials; Antimycobacterial activity; Antiplasmodial activity; carbon; Cycloartane-type triterpenoid; Cytotoxic activity; cytotoxicity; Dasymaschalon dasymaschalum; Flavanone; humans; inhibitory concentration 50; leaves; lung neoplasms; Mycobacterium; nuclear magnetic resonance spectroscopy; stable isotopes; triterpenoids
• ISSN: 1874-3900; 1876-7486
• DOI: 10.1016/j.phytol.2013.03.002

Two new cycloartane-type triterpenoids, one new flavanone, two new natural products of benzoate derivative, and ten known compounds were isolated from the leaves of Dasymaschalon dasymaschalum. The structures of these compounds were established on the basis of spectroscopic data and comparison with reported values. Antimycobacterial, antiplasmodial and cytotoxic activities of the isolates were evaluated. •Two new cycloartane-type triterpenoids and a new flavanone were isolated from the leaves of Dasymaschalon dasymaschalum.•The structures were elucidated by the use of spectroscopic methods including UV, IR, HR-TOF-MS, 1D and 2D NMR.•The antiplasmodial, antimycobacterial and cytotoxic activities of the isolates were evaluated.•New compound 5 showed good cytotoxicity in NCI-H187 cells with an IC50 value of 1.85μg/mL. Two new cycloartane-type triterpenoids, 3β-hydroxy-21-O-acetyl-24-methylenecycloartane (3) and 3β,21-dihydroxy-24,31-epoxy-24-methylenecycloartane (4), one new flavanone, 7-hydroxy-6,8-dimethoxyflavanone (5), two new natural products, 2-hydroxybenzyl benzoate (7) and 2-phenyl-2-acetoxyethyl benzoate (8), and ten known compounds, 3β-hydroxy-24-methylenecycloartane (1), 3β,21-dihydroxy-24-methylenecycloartane (2), desmosdumotin B (6), artabotrene (9), (−)-senepoxide (10), (+)-crotepoxide (11), (−)-1,6-desoxypipoxide (12), rotundol (13), cassipourol (14) and (+)-spathulenol (15) were isolated from the leaves of Dasymaschalon dasymaschalum. The structures of the new compounds were elucidated by spectroscopic analysis and of the known compounds by comparison of their physical, UV, IR, 1H and 13C NMR data with those of published compounds. Antimycobacterial, antiplasmodial and cytotoxic activities of the isolates, except 8 and 10 were evaluated. Compounds 1, 4, 5, 11, 12 and 15 exhibited potent cytotoxic activities against human lung cancer cell lines (NCI-H187) with respective IC50 values of 4.67, 7.82, 1.85, 6.33, 3.07 and 6.68μg/mL.