title: Transformation of xanthohumol by Aspergillus ochraceus.
abstract: Microbial transformation of xanthohumol isolated from agro-residue (spent hops), by Aspergillus ochraceus was investigated. A new aurone, (Z)-2″-(2‴-hydroxyisopropyl)-dihydrofurano[4″,5″:6,7]-3',4'-dihydroxy-4-methoxyaurone, was obtained as a main transformation product. Three minor metabolites were identified as 2″-(2‴-hydroxyisopropyl)-dihydrofurano[4″,5″:3',4']-2',4-dihydroxy-6'-methoxychalcone, (2S,2″S)-2″-(2‴-hydroxyisopropyl)-dihydrofurano[4″,5″:7,8]-4'-hydroxy-5-methoxyflavanone and (2S,2″R)-2″-(2‴-hydroxyisopropyl)-dihydrofurano[4″,5″:7,8]-4'-hydroxy-5-methoxyflavanone. Their structures were elucidated on the basis of spectroscopic evidences. The antioxidant properties of xanthohumol and its metabolites were investigated using the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The major biotransformation product, was 8.6-fold stronger antioxidant than xanthohumol and 2.3-fold than ascorbic acid.
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Tomasz
authors: T
authors: Tronina
authors: Agnieszka
authors: A
authors: Bartmańska
authors: Jarosław
authors: J
authors: Popłoński
authors: Ewa
authors: E
authors: Huszcza
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000378:metabolism; D001235:Aspergillus ochraceus / Q000378:metabolism*; D001572:Benzofurans / Q000302:isolation & purification*; D001597:Benzylidene Compounds / Q000302:isolation & purification*; D001711:Biotransformation; D005419:Flavonoids / Q000737:chemistry* / Q000378:metabolism; D011427:Propiophenones / Q000737:chemistry* / Q000378:metabolism
chemical_list: C000590117:2'-(2''-hydroxyisopropyl)-dihydrofurano(4',5'-6,7)-3',4'-dihydroxy-4-methoxyaurone; D000975:Antioxidants; D001572:Benzofurans; D001597:Benzylidene Compounds; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol
keywords: Antioxidants; Aspergillus ochraceus; Aurone; Biotransformation; Flavonoid; Xanthohumol