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Structures of Phytosterols and Triterpenoids with Potential Anti-Cancer Activity in Bran of Black Non-Glutinous Rice

Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
Department of Basic Science and Physical Education, Faculty of Science at Si Racha, Kasetsart University, Si Racha Campus, Chonburi 20230, Thailand
Department of Anatomy, Faculty of Science, Mahidol University, Bangkok 10400, Thailand
Author to whom correspondence should be addressed.
Nutrients 2015, 7(3), 1672-1687;
Received: 26 October 2014 / Revised: 13 February 2015 / Accepted: 25 February 2015 / Published: 6 March 2015
Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80–467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract. View Full-Text
Keywords: rice bran; anti-cancer; gramisterol; lupeol; GC-MS; LC-MS rice bran; anti-cancer; gramisterol; lupeol; GC-MS; LC-MS
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Suttiarporn, P.; Chumpolsri, W.; Mahatheeranont, S.; Luangkamin, S.; Teepsawang, S.; Leardkamolkarn, V. Structures of Phytosterols and Triterpenoids with Potential Anti-Cancer Activity in Bran of Black Non-Glutinous Rice. Nutrients 2015, 7, 1672-1687.

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