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Molecules 2014, 19(3), 3389-3400; https://doi.org/10.3390/molecules19033389

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

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
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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. View Full-Text
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
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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.

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