Sterol ferulates, sterols, and 5-alk(en)ylresorcinols from wheat, rye, and corn bran oils and their inhibitory effects on Epstein-Barr virus activation.
Sterol ferulate, free sterol, and 5-alk(en)ylresorcinol constituents of wheat, rye, and corn bran oils were studied. Among the sterol ferulates, one novel compound, 24-methylenecholestanol ferulate (7), along with six known compounds, namely, 24-methylcholestanol ferulate (1), 24-methylcholesterol ferulate (2), 2-methyllathosterol ferulate (3), stigmastanol ferulate (4), sitosterol ferulate (5), and schottenol ferulate (6), were isolated and characterized. Five known free sterols, namely, 24-methylcholesterol (8), stigmastanol (9), sitosterol (10), schottenol (11), and stigmasterol (12), were isolated and identified. 5-Alk(en)ylresorcinols were found in wheat and rye bran oils but not in corn bran oil. Of these, one new compound, 5-n-(2'-oxo-14'-Z-heneicosenyl) resorcinol (19), and seven known compounds, namely, 5-n-heptadecyl- (13), 5-n-nonadecyl- (14), 5-n-heneicosyl- (15), 5-n-tricosyl- (16), 5-n-pentacosyl- (17), 5-n-(14'-Z-nonadecenyl)- (18), and 5-n-(2'-oxoheneicosyl)resorcinols (20), were isolated and characterized. These compounds were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. Four compounds, 1, 2, 4, and 11, showed potent inhibitory effects on EBV-EA induction.
K-Laboratories for Intelligent Medical Remote Services, 2266-22 Anagahora, Shimoshidami, Moriyama-ku, Nagoya 463-0003, Japan.
Kenji
K
Iwatsuki
Toshihiro
T
Akihisa
Harukuni
H
Tokuda
Motohiko
M
Ukiya
Hiroshi
H
Higashihara
Teruo
T
Mukainaka
Masao
M
Iizuka
Yoshiharu
Y
Hayashi
Yumiko
Y
Kimura
Hoyoku
H
Nishino
D003373:Coumaric Acids / Q000032:analysis* / Q000494:pharmacology; D002523:Edible Grain / Q000737:chemistry*; D004854:Herpesvirus 4, Human / Q000187:drug effects / Q000502:physiology*; D010840:Phytosterols / Q000032:analysis* / Q000494:pharmacology; D010938:Plant Oils / Q000737:chemistry; D012118:Resorcinols / Q000032:analysis* / Q000494:pharmacology; D012434:Secale / Q000737:chemistry; D014908:Triticum / Q000737:chemistry; D014775:Virus Activation / Q000187:drug effects*; D003313:Zea mays / Q000737:chemistry
D003373:Coumaric Acids; D010840:Phytosterols; D010938:Plant Oils; D012118:Resorcinols; C004999:ferulic acid