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

1
Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
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Department of Basic Science and Physical Education, Faculty of Science at Si Racha, Kasetsart University, Si Racha Campus, Chonburi 20230, Thailand
3
Department of Anatomy, Faculty of Science, Mahidol University, Bangkok 10400, Thailand
*
Author to whom correspondence should be addressed.
Nutrients 2015, 7(3), 1672-1687; https://doi.org/10.3390/nu7031672
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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