Azaphilones, Furanoisophthalides, and Amino Acids from the Extracts of <i>Monascus pilosus</i>-Fermented Rice (Red-Mold Rice) and Their Chemopreventive Effects

Abstract

Six azaphilones, monascin ( 1 ), ankaflavin ( 2 ), rubropunctatin ( 3 ), monascorburin ( 4 ), rubropunctamine ( 5 ), and monascorburamine ( 6 ), two furanoisophthalides, xanthomonasin A ( 7 ) and xanthomonasin B ( 8 ), and two amino acids, (+)-monascumic acid ( 9 ) and (−)-monascumic acid ( 10 ), isolated from the extracts of Monascus pilosus -fermented rice (red-mold rice) were evaluated for their inhibitory effects on 12- O -tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, on the induction of Epstein−Barr virus early antigen (EBV-EA) by TPA in Raji cells, and on the activation of (±)-( E )-methyl-2[( E )-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor. Among the compounds tested, seven compounds ( 1 − 6 and 10 ) on TPA-induced inflammation, and six compounds ( 1, 3 − 5, 9, and 10 ) on EBV-EA activation, exhibited potent inhibitory effects. All of the compounds tested showed moderate inhibitory effects on NOR 1 activation. Keywords: Monascus pilosus; red-mold rice; azaphilones; furanoisophthalides; amino acids; TPA-induced ear edema; antitumor-promoter; Epstein−Barr virus early antigen