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Transformation of xanthohumol by Aspergillus ochraceus
Author(s) -
Tronina Tomasz,
Bartmańska Agnieszka,
Popłoński Jarosław,
Huszcza Ewa
Publication year - 2014
Publication title -
journal of basic microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.58
H-Index - 54
eISSN - 1521-4028
pISSN - 0233-111X
DOI - 10.1002/jobm.201200320
Subject(s) - xanthohumol , aspergillus ochraceus , chemistry , biotransformation , dpph , antioxidant , ascorbic acid , residue (chemistry) , stereochemistry , food science , biochemistry , hop (telecommunications) , ochratoxin a , enzyme , mycotoxin , computer network , computer science
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, (2 S ,2″ S )‐2″‐( 2 ‴ ‐hydroxyisopropyl)‐dihydrofurano[4″,5″:7,8]‐4′‐hydroxy‐5‐methoxyflavanone and (2 S ,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.