Next Article in Journal
Regioselective Electrophilic Aromatic Bromination: Theoretical Analysis and Experimental Verification
Previous Article in Journal
Laccase Immobilized on a PAN/Adsorbents Composite Nanofibrous Membrane for Catechol Treatment by a Biocatalysis/Adsorption Process
Molecules 2014, 19(3), 3389-3400; doi:10.3390/molecules19033389
Article

An Unusual 2,3-Secotaraxerene and Other Cytotoxic Triterpenoids from Pleiocarpa pycnantha (Apocynaceae) Leaves Collected from Nigeria

1, 2, 1, 1 and 1,*
1 Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa 2 Department of Biotechnology, Apoptosis Research Unit, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa
* Author to whom correspondence should be addressed.
Received: 18 January 2014 / Revised: 26 February 2014 / Accepted: 11 March 2014 / Published: 20 March 2014
View Full-Text   |   Download PDF [670 KB, uploaded 18 June 2014]   |  

Abstract

Three known triterpenoids, namely ursolic acid (1), and the 27-E- and 27-Z-p-coumaric esters of ursolic acid (compounds 2, 3), were isolated together with a new triterpene 2,3-seco-taraxer-14-en-2,3-lactone [pycanocarpine (4)] from an ethanolic extract of Pleiocarpa pycnantha leaves. The structure of 4 was unambiguously assigned using NMR, HREIMS and X-ray crystallography. The cytotoxic activities of the compounds were evaluated against HeLa, MCF-7, KMST-6 and HT-29 cells using the WST-1 assay. Ursolic acid (1) displayed potent cytotoxic activity against HeLa, HT-29 and MCF-7 cells with IC50 values of 10, 10 and 20 µM respectively. The new compound 4 and its hydrolysed derivative 5 were selectively cytotoxic to the breast cancer cell line, MCF-7 with IC50 values 20 and 10 µM respectively. This is the first report on isolation of a 2,3-seco-taraxerene derivative from the Apocynaceae family and cytotoxic activityof P. pycnantha constituents.
Keywords: Pleiocarpa pycnantha; Apocynaceae; triterpenoids; cytotoxicity; 2,3-seco-taraxerene; ursolic acid; WST-1 Pleiocarpa pycnantha; Apocynaceae; triterpenoids; cytotoxicity; 2,3-seco-taraxerene; ursolic acid; WST-1
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Omoyeni, O.A.; Meyer, M.; Iwuoha, E.; Green, I.; Hussein, A.A. An Unusual 2,3-Secotaraxerene and Other Cytotoxic Triterpenoids from Pleiocarpa pycnantha (Apocynaceae) Leaves Collected from Nigeria. Molecules 2014, 19, 3389-3400.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert