Structure Elucidation and Chemical Profile of Sphingolipids in Wheat Bran and Their Cytotoxic Effects against Human Colon Cancer Cells

• Published in: Journal of agricultural and food chemistry 2013-01, Vol.61 (4), p.866-874
• Main Authors: Zhu, Yingdong, Soroka, Dominique N, Sang, Shengmin
• Format: Article
• Language: English
• Subjects: Anticarcinogenic Agents - pharmacology; Antineoplastic Agents, Phytogenic; Biological and medical sciences; Cell Survival - drug effects; Cereal and baking product industries; Colonic Neoplasms - pathology; Colonic Neoplasms - prevention & control; colorectal neoplasms; cytotoxicity; Dietary Fiber - analysis; Food industries; foods; Fundamental and applied biological sciences. Psychology; growth retardation; HCT116 Cells; HT29 Cells; Humans; Molecular Structure; nuclear magnetic resonance spectroscopy; Spectrometry, Mass, Electrospray Ionization; sphingolipids; Sphingolipids - analysis; Sphingolipids - chemistry; Sphingolipids - pharmacology; wheat bran
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf3047863

Sphingolipids are known to have diverse properties and physiological functions. These distinctive lipids have been identified in wheat bran, a food well-known for its chemopreventive activity. However, the complete profile of sphingolipids in wheat bran and their contributions to the cancer preventive effect of wheat bran have not been fully explored until this study. Twelve sphingolipids (1–12) were purified from wheat bran extract and characterized by analyzing their 1D and 2D NMR spectra, and seven sphingolipids (13–19) were characterized based on their tandem mass spectra (MS n : n = 2–4). To the best of our knowledge, this is the first report of sphingolipids 1, 6–9, 11–14, and 16–19 in wheat bran. In particular, 2-N-(2′-hydroxy-15′-tricosenoyl)-4-hydroxysphinganine (peak 17) is a novel compound. Additionally, compounds 2–4 were reported with complete NMR data for the first time. Sphingolipids (1–12) showed little growth inhibition against human colon cancer cell lines (HCT-116 and HT-29) in vitro.