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Paper | Regular issue | Vol 41, No. 4, 1995, pp.741-752
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6980
Additional Bioactive Triterpenoids from Melia volkensii (Meliaceae)

Lu Zeng, Zhe-ming Gu, Phillip E. Fanwick, Ching-jer Chang, David L. Smith, and Jerry L. McLaughlin

*Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, U.S.A.

Abstract

Meliavolen (1) and melianinone (2), new triterpenes with an apotirucallane skeleton, together with two known compounds, 3-episapelin A (5) and nimbolin B (6), have been isolated from the root bark of Melia volkensii (Meliaceae) by using brine shrimp lethality for bioactivity-directed fractionation. The structures have been elucidated by spectral data. The relative and absolute stereochemistries of 2 were determined by correlating 2 with melianin A (3). The stereochemistry of 3 was determined by X-ray crystallographic analysis and Mosher methodology. The stereochemistry of 5 was also determined by Mosher methodology. The four isolated compounds, meliavolen (1), melianinone (2), 3-episapelin (5), and nimbolin B (6), were all moderately active in the brine shrimp lethality test and were significantly cytotoxic among human solid tumor cell lines with noted selectivities toward the colon cell line (HT-29).