Structure-activity relationships of retro-dihydrochalcones isolated from tacca sp.

Jiangnan Peng, April L. Risinger, Chenxiao Da, Gary A. Fest, Glen E. Kellogg, Susan L. Mooberry

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

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-E (1-4) 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-activity relationships for this compound class concerning its antiproliferative and microtubule depolymerizing activities.

Original languageEnglish (US)
Pages (from-to)2189-2194
Number of pages6
JournalJournal of Natural Products
Volume76
Issue number12
DOIs
StatePublished - Dec 27 2013

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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