Bioorganic & Medicinal Chemistry 2011-07-01

5-alk(en)ylresorcinols as the major active components in wheat bran inhibit human colon cancer cell growth.

Yingdong Zhu, Dawn R Conklin, Huadong Chen, Liyan Wang, Shengmin Sang

Index: Bioorg. Med. Chem. 19 , 3973-82, (2011)

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Abstract

We and others have found that wheat bran oil is the active constituent in wheat bran for colon cancer prevention. However, the active components in wheat bran oil are still unknown. Using human colon cancer cells (HCT-116 and HT-29) as the guiding assays, we further purified the active components from wheat bran using column chromatography. In this study, we identified that a fraction containing 5-n-alk(en)ylresorcinols had the strongest inhibitory effect on the proliferation of human HCT-116 and HT-29 colon cancer cells. Further purification led to the identification of 14 5-alk(en)ylresorcinols. Among them, 7, (10'Z,13'Z,16'Z)-5-(nonadeca-10',13',16'-trienyl)resorcinol, is a novel compound and 5, 6, 9, 10, and 13 were purified as individual compounds for the first time. The identification and structural elucidation of these compounds were based on 1D and 2D NMR and tandem mass spectral analyses. All these compounds (1-14) except 10 were evaluated for growth inhibition of human colon cancer cell lines (HCT-116 and HT-29). Our results indicate that increasing the length of the side chain will diminish the inhibitory activity, and the existence of a double bond and a carbonyl group will strengthen such an activity.Copyright © 2011 Elsevier Ltd. All rights reserved.