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Title: Anticancer activity of branched-chain derivatives of oleic acid

Author
item Dailey Jr, Oliver
item WANG, XI - CLEMSON UNIVERSITY
item CHEN, FENG - CLEMSON UNIVERSITY
item HUANG, GOUHUI - Clemson University

Submitted to: Anticancer Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/10/2011
Publication Date: 10/1/2011
Citation: Dailey Jr, Oliver, D., Wang, XI., Chen, Feng, Huang, Guohui. 2011. Anticancer activity of branched-chain derivatives of oleic acid. Anticancer Research. 31(10):3165-3170.

Interpretive Summary: Oleic acid and linoleic acid are the most abundant fatty acids of many vegetable oils, including cottonseed oil. As part of a project to develop new value-added industrial applications for cottonseed oil, studies were conducted in the synthetic conversion of oleic acid to branched-chain fatty acids. In these studies, methyl oleate was converted in a series of reactions to several different branched-chain derivatives. These compounds and their fatty acid counterparts were tested in vitro for their anticancer activities against two cancer cell lines--MCF-7 (human breast) and HT-29 (human colon). In addition two tertiary alcohols obtained as side-products in the synthesis of the branched-chain derivatives were tested. Two branched-chain derivatives of oleic acid exhibited highly significant antitumor activity. This research benefits farmers of cotton and other oilseed crops, oil chemists, and the pharmaceutical industry in that it demonstrates that certain products derived from oilseeds show promise as potent anticancer agents.

Technical Abstract: A number of novel branched-chain derivatives (methyl, n-butyl, phenyl) of methyl oleate were produced by bromination in the allylic position and subsequent treatment with organocuprate reagents. These compounds and their free acid counterparts were tested in vitro for their antiproliferative activities against two cancer cell lines--MCF-7 (human breast) and HT-29 (human colon). In addition two tertiary alcohols obtained as side-products in the synthesis of the branched-chain derivatives were tested. Testing was performed at three concentration levels (50, 100, and 200 ppm). The greatest growth inhibitory activity was exhibited by the branched phenyl derivative of oleic acid (cell viability was kept below 50% for both cell lines at all three concentrations). The branched n-butyl derivative of oleic acid also exhibited highly significant activity (cell viability at ca. 30% at 100 and 200 ppm concentration levels)