title: Biotransformation of turmerones by Aspergillus niger.
abstract: Biotransformation studies conducted on (+)-(S)-ar-turmerone (1) and (+)-(S)-dihydro-ar-turmerone (2) by the fungus Aspergillus niger have revealed that 1 was metabolized to give four oxidized metabolites, (+)-(7S)-hydroxydehydro-ar-todomatuic acid (3), (+)-(7S,10E)-12-hydroxydehydro-ar-todomatuic acid (4), (+)-(7S,10E)-7,12-dihydroxydehydro-ar-todomatuic acid (5), and (+)-(7S)-15-carboxy-9,13-epoxy-7-hydroxy-9,13-dehydro-ar-curcumene (6), and (+)-(S)-dihydro-ar-turmerone (2) was metabolized to (+)-7,11-dihydroxy-ar-todomatuic acid (7). Metabolites 3-7 were characterized using spectroscopic techniques. Metabolites 3-7 inhibited acetylcholinesterase (AChE) although less so than the parent substrates.
authors.affiliation: Department of Applied Chemistry, Faculty of Science of Engineering, Kinki University, 3-4-1, Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan.
authors.forename: Mai
authors.initials: M
authors.lastname: Fujiwara
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Marumoto
authors.forename: Nobuo
authors.initials: N
authors.lastname: Yagi
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D001234:Aspergillus niger / Q000378:metabolism*; D001711:Biotransformation; D002800:Cholinesterase Inhibitors / Q000097:blood / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D013172:Spores, Fungal / Q000378:metabolism; D013237:Stereoisomerism; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D002800:Cholinesterase Inhibitors; D007659:Ketones; D012717:Sesquiterpenes; C078098:ar-turmerone; D014050:Toluene; C086829:alpha-curcumene