Isolation, Structure Elucidation, and Biological Evaluation of 16,23-Epoxycucurbitacin Constituents from Eleaocarpus chinensis

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• 作者：Li Pan ; Yeonjoong Yong ; Ye Deng ; Daniel D. Lantvit ; Tran Ngoc Ninh ; Heebyung Chai ; Esperanza J. Carcache de Blanco ; Djaja D. Soejarto ; Steven M. Swanson ; A. Douglas Kinghorn
• 刊名：Journal of Natural Products
• 出版年：2012
• 出版时间：March 23, 2012
• 年：2012
• 卷：75
• 期：3
• 页码：444-452
• 全文大小：302K
• 年卷期：v.75,no.3(March 23, 2012)
• ISSN：1520-6025

文摘

Eight new 16,23-epoxycucurbitacin derivatives, designated as elaeocarpucins A鈥揌 (1鈥?b>8), and five known cucurbitacins (9鈥?b>13) were isolated from the chloroform-soluble partitions of separate methanol extracts of the fruits and stem bark of Elaeocarpus chinensis collected in Vietnam. Isolation work was facilitated using a LC/MS dereplication procedure, and bioassay-guided fractionation was monitored using HT-29 human cancer cells. The structures of compounds 1鈥?b>8 were determined on the basis of spectroscopic data interpretation, with the absolute configurations of isomers 1 and 2 established by the Mosher ester method. Compounds 1鈥?b>13 were evaluated in vitro against the HT-29 cell line and using a mitochondrial transmembrane potential assay. Elaeocarpucin C (3), produced by partial synthesis from 16伪,23伪-epoxy-3尾,20尾-dihydroxy-10伪H,23尾H-cucurbit-5,24-dien-11-one (13), was found to be inactive when evaluated in an in vivo hollow fiber assay using three different cancer cell types (dose range 0.5鈥?0 mg/kg/day, ip).