title: Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice.
abstract: 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.
authors.affiliation: Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand. panawansut@gmail.com.
authors.forename: Panawan
authors.initials: P
authors.lastname: Suttiarporn
authors.affiliation: Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand. watcharapong_chum@hotmail.com.
authors.forename: Watcharapong
authors.initials: W
authors.lastname: Chumpolsri
authors.affiliation: Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand. sugunya.m@cmu.ac.th.
authors.forename: Sugunya
authors.initials: S
authors.lastname: Mahatheeranont
authors.affiliation: Department of Basic Science and Physical Education, Faculty of Science at Si Racha, Kasetsart University, Si Racha Campus, Chonburi 20230, Thailand. lsuwaporn@gmail.com.
authors.forename: Suwaporn
authors.initials: S
authors.lastname: Luangkamin
authors.affiliation: Department of Anatomy, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. jookkajoon_pt@hotmail.com.
authors.forename: Somsuda
authors.initials: S
authors.lastname: Teepsawang
authors.affiliation: Department of Anatomy, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. vijittra.lea@mahidol.ac.th.
authors.forename: Vijittra
authors.initials: V
authors.lastname: Leardkamolkarn
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D045744:Cell Line, Tumor; D002784:Cholesterol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D007938:Leukemia / Q000188:drug therapy*; D013058:Mass Spectrometry; D051379:Mice; D015394:Molecular Structure; D012275:Oryza / Q000737:chemistry*; D053978:Pentacyclic Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D012639:Seeds / Q000737:chemistry*; D012855:Sitosterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D013265:Stigmasterol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D000094042:Lupanes
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D002784:Cholesterol; D053978:Pentacyclic Triterpenes; D010840:Phytosterols; D010936:Plant Extracts; D012855:Sitosterols; D013265:Stigmasterol; D014315:Triterpenes; C470592:lupenone; D000094042:Lupanes; C015896:fucosterol; C021273:campesterol; C025473:gamma-sitosterol; C007198:cycloleucalenol; C010480:lupeol