title: Suppression of SOS-inducing activity of chemical mutagens by metabolites from microbial transformation of (-)-isolongifolene.
abstract: In this study, biotransformation of (-)-isolongifolene (1) by Glomerella cingulata and suppressive effect on umuC gene expression by chemical mutagens 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide) and aflatoxin B(1) (AFB(1)) of the SOS response in Salmonella typhimurium TA1535/pSK1002 were investigated. Initially, 1 was carried out the microbial transformation by G. cingulata. The result found that 1 was converted into (-)-isolongifolen-9-one (2), (-)-(2S)-13-hydroxy-isolongifolen-9-one (3), and (-)-(4R)-4-hydroxy-isolongifolen-9-one (4) by G. cingulata, and their conversion rates were 60, 25, and 15%, respectively. The metabolites suppressed the SOS-inducing activity of furylfuramid and AFB(1) in the umu test. Comound 2 showed gene expression by chemical mutagens furylfuramide and AFB(1) was suppressed 54 and 50% at <0.5 mM, respectively. Compound 2 is the most effective compound in this experiment.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosakashi, Osaka 577-8502, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Sakata
authors.forename: Yoshimitsu
authors.initials: Y
authors.lastname: Oda
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D016604:Aflatoxin B1 / Q000494:pharmacology; D001711:Biotransformation; D004249:DNA Damage; D004261:DNA Replication; D005668:Furylfuramide / Q000494:pharmacology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009153:Mutagens / Q000302:isolation & purification / Q000494:pharmacology*; D020081:Phyllachorales / Q000378:metabolism; D028223:Pinus; D013014:SOS Response, Genetics / Q000187:drug effects*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*
chemical_list: D009153:Mutagens; D012717:Sesquiterpenes; C538771:isolongifolenone; D005668:Furylfuramide; D016604:Aflatoxin B1