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Structure type: monomer
C₂₂H₂₂O₉
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7275
  Herath W, Mikell JR, Hale AL, Ferreira D, Khan IA "Microbial metabolism part 9. Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones" - Chemical and Pharmaceutical Bulletin 56(4) (2008) 418-422
  

  5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4'-hydroxychrysin (4), chrysin 7-O-β-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4'-hydroxy-3'-methoxychrysin (chrysoeriol) (7), 4'-hydroxychrysin (apigenin) (4) 3',4'-dihydroxychrysin (luteolin) (8), 3'-methoxychrysin 4'-O-α-D-6-deoxyallopyranoside (9), chrysin 4'-O-α-D-6-deoxyallopyranoside (10), and luteolin 3'-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4'-dihydroxyflavone (12) and 4'-hydroxyflavone 5-O-β-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-β-D-4-O-methylglucopyranoside (15) and (+/-)-flavanone 6-O-β-D-4-O-methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed.

  flavonoid, microbial metabolism, Beauveria bassiana, Aspergillus alliaceus, Absidia glauco, Mucore ramannianus

  NCBI PubMed ID: 18379084
  Publication DOI: 10.1248/cpb.56.418
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Correspondence: ikhan@olemiss.edu
  Institutions: National Center for Natural Products Research, The University of Mississippi, Mississippi, USA, Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, Mississippi, USA
  Methods: 13C NMR, 1H NMR, TLC, biological assays, FTIR, UV, extraction, optical rotation measurement, CC, HR-ESI-MS
  
   
  
  Beauveria bassiana ATCC 13144
  CSDB ID 43473 (all data & tools)

Show legend Show as text

Structure type: monomer ; 430.4
C₂₂H₂₂O₉
Compound class: glucoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8562
  Dymarska M, Janeczko T, Kostrzewa-Suslow E "Biotransformations of flavones and an isoflavone (daidzein) in cultures of entomopathogenic filamentous fungi" - Molecules 23(6) (2018) E1356 (1-15)
  

  Entomopathogenic filamentous fungi of the genus Isaria are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species Isariafumosorosea and Isariafarinosa isolated from the environment were used. Their catalytic capacity to carry out biotransformations of flavones-unsubstituted, with hydroxy- and amino-substituents as well as a hydroxylated isoflavone-was investigated. Biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, and daidzein resulted in the formation of O-methylglucosides, in the case of flavone and 5-hydroxyflavone with additional hydroxylations. 7-Aminoflavone was transformed into two acetamido derivatives. The following products were obtained: From flavone⁻flavone 2'-O-β-D-(4''-O-methyl)-glucopyranoside, flavone 4'-O-β-D-(4''-O-methyl)-glucopyranoside and 3'-hydroxyflavone 4'-O-β-D-(4''-O-methyl)-glucopyranoside; from 5-hydroxyflavone⁻5-hydroxyflavone 4'-O-β-D-(4''-O-methyl)-glucopyranoside; from 6-hydroxyflavone⁻flavone 6-O-β-D-(4''-O-methyl)-glucopyranoside; from 7-hydroxyflavone⁻flavone 7-O-β-D-(4''-O-methyl)-glucopyranoside; from daidzein⁻daidzein 7-O-β-D-(4''-O-methyl)-glucopyranoside; and from 7-aminoflavone⁻7-acetamidoflavone and 7-acetamido-4'-hydroxyflavone. Seven of the products obtained by us have not been previously reported in the literature.

  biotransformations, flavone, daidzein, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, 7-aminoflavone, Isaria fumosorosea, Isaria farinosa

  NCBI PubMed ID: 29874813
  Publication DOI: 10.3390/molecules23061356
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Dymarska M ; Janeczko T ; Kostrzewa-Suslow E
  Institutions: Department of Chemistry, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, TLC, HPLC, optical rotation measurement, HMBC, COSY, HSQC
  
   
  
  Isaria fumosorosea KCH J2, Isaria farinosa J1.4
  CSDB ID 48709 (all data & tools)