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Triterpene Alcohol and Sterol Ferulates from Rice Bran and Their Anti-inflammatory Effects

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College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan, College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan, Application Development Department, Yokogawa Analytical Systems Inc., 2-11-13 Nakacho, Musashino, Tokyo 101-0006, Japan, and Meikai University School of Dentistry, 1-1 Keyakidai, Sakado, Saitama 350-0283, Japan
Cite this: J. Agric. Food Chem. 2000, 48, 6, 2313–2319
Publication Date (Web):May 26, 2000
https://doi.org/10.1021/jf000135o
Copyright © 2000 American Chemical Society
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    Abstract

    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 μg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID50) was 0.1−0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID50 0.2−0.3 mg/ear), eight free sterols examined showed weaker activity (ID50 0.7−2.7 mg/ear) than their corresponding ferulates.

    Keywords: Rice bran; trans- and cis-feruloyl esters; triterpene alcohol; sterol; antiedema; TPA-induced ear edema

    *

     Author to whom correspondence should be addressed (fax +81-3-3293-7572; e-mail [email protected]).

    †

     College of Science and Technology, Nihon University.

    ‡

     College of Pharmacy, Nihon University.

    §

     Yokogawa Analytical Systems Inc.

    ⊥

     Meikai University School of Dentistry.

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