Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects.
Six novel feruloyl esters of triterpene alcohols and sterols, viz., two trans-ferulates, cycloeucalenol and 24-methylenecholesterol trans-ferulates, and four cis-ferulates, cycloartenol, 24-methyelenecycloartanol, 24-methylcholesterol, and sitosterol cis-ferulates, besides five known trans-ferulates, cycloartenol (CAR), 24-methylenecycloartanol (24-MCA), 24-methylcholesterol, sitosterol, and stigmastanol trans-ferulates, and one known cis-ferulate, stigmastanol cis-ferulate, were isolated from the methanol extract of edible rice bran. These and eight other synthetic trans- and cis-ferulates of triterpene alcohols and sterols, along with the corresponding free alcohols, were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID(50)) was 0. 1-0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID(50) 0.2-0.3 mg/ear), eight free sterols examined showed weaker activity (ID(50) 0.7-2.7 mg/ear) than their corresponding ferulates.
Akihisa
T
T
College of Science and Technology, Nihon University, Tokyo, Japan. akihisa@chem.cst.nihon-u.ac.jp
Yasukawa
K
K
Yamaura
M
M
Ukiya
M
M
Kimura
Y
Y
Shimizu
N
N
Arai
K
K
D000438:Alcohols / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000302:isolation & purification* / Q000494:pharmacology; D003373:Coumaric Acids / Q000302:isolation & purification* / Q000494:pharmacology; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005260:Female; D051379:Mice; D008813:Mice, Inbred ICR; D012275:Oryza / Q000737:chemistry*; D013261:Sterols / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013755:Tetradecanoylphorbol Acetate; D014315:Triterpenes / Q000302:isolation & purification* / Q000494:pharmacology
D000438:Alcohols; D000893:Anti-Inflammatory Agents; D003373:Coumaric Acids; D013261:Sterols; D014315:Triterpenes; C004999:ferulic acid; D013755:Tetradecanoylphorbol Acetate