Isolation and synthesis of two antiproliferative calamenene-type sesquiterpenoids from Sterculia tavia from the Madagascar rain forest.

Abstract

Investigation of the endemic Madagascan plant Sterculia taiva Baill. (Malvaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of two new bioactive calamenene-type sesquiterpenoids, named tavinin A (2) and epi-tavinin A (3) together with the known sesquiterpenoid mansonone G (1). The structures of the two new compounds were elucidated based on analysis of their 1D and 2D NMR spectra and mass spectrometric data, and were confirmed by de novo synthesis. The three isolated sesquiterpenoids (1-3) had modest antiproliferative activities against the A2780 ovarian cancer cell line, with IC(50) values of 10.2, 5.5 and 6.7 μM, respectively.

• Authors: Yumin Dai, Liva Harinantenaina, Peggy J Brodie, Martin W Callmander, Sennen Randrianasolo, Etienne Rakotobe, Vincent E Rasamison, David G I Kingston
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 20 Issue 24 Pg. 6940-4 (Dec 15 2012) ISSN: 1464-3391 [Electronic] England
• PMID: 23149304 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
• Copyright: Copyright © 2012 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents, Phytogenic
• Plant Extracts
• Polycyclic Sesquiterpenes
• Sesquiterpenes
• Terpenes
• calamenene

Topics

• Antineoplastic Agents, Phytogenic (chemical synthesis, chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• Female
• Humans
• Madagascar
• Ovarian Neoplasms (drug therapy)
• Plant Extracts (chemical synthesis, chemistry, isolation & purification, pharmacology)
• Polycyclic Sesquiterpenes
• Sesquiterpenes (chemical synthesis, chemistry, isolation & purification, pharmacology)
• Sterculia (chemistry)
• Terpenes (chemical synthesis, chemistry, isolation & purification, pharmacology)