Structure–Activity Relationships of Retro-dihydrochalcones Isolated from Tacca sp.

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• 作者：Jiangnan Peng ; April L. Risinger ; Chenxiao Da ; Gary A. Fest ; Glen E. Kellogg ; Susan L. Mooberry
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：December 27, 2013
• 年：2013
• 卷：76
• 期：12
• 页码：2189-2194
• 全文大小：293K
• ISSN：1520-6025

文摘

Several biologically active compounds have been identified from Tacca species, including glycosides, diarylheptanoids, saponins, withanolides, and the taccalonolide class of microtubule stabilizers. More recently, two cytotoxic retro-dihydrochalcones named evelynin A (7) and taccabulin A (6) were isolated and their biological activities characterized, including the finding that taccabulin has microtubule destabilizing effects. Here we describe the identification and characterization of five new retro-chalcones, named taccabulins B鈥揈 (1鈥?b>4) and evelynin B (5) from Tacca sp. extracts. Their structures were determined using 1D and 2D NMR as well as mass spectroscopic data and modeled into the colchicine binding site of tubulin. The antiproliferative and microtubule effects of each compound were determined experimentally and found to be well correlated with modeling studies. The isolation and biological characterization of several retro-dihydrochalcones facilitated preliminary structure鈥揳ctivity relationships for this compound class concerning its antiproliferative and microtubule depolymerizing activities.