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1. (Article ID: 7279)
Herath W, Mikell JR, Hale AL, Ferreira D, Khan IA
Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones
Chemical and Pharmaceutical Bulletin 54(3) (2006)
320-324
Fermentation of 3-hydroxyflavone (1) with Beauveria bassiana (ATCC 13144) yielded 3,4'-dihdroxyflavone (3), flavone 3-O-β-D-4-O-methylglucopyranoside (4) and two minor metabolites. 7-Hydroxyflavone (2) was transformed by Nocardia species (NRRL 5646) to 7-methoxyflavone (5) whilst Aspergillus alliaceus (ATCC 10060) converted it to 4',7-dihydroxyflavone (6). Flavone 7-O-β-D-4-O-metylglucopyranoside (7) and 4'-hydroxyflavone 7-O-β-D-4-O-methylglucopyranoside (8) were the metabolic products of 7-hydroxyflavone (2) when fermented with Beauveria bassiana (ATCC 7159). One of the minor metabolites of 3-hydroxyflavone (1) was tentatively assigned a β'-chalcanol structure (9). Compounds 4, 7 and 8 are reported as new compounds. Structure elucidation of the metabolites was based on spectroscopic data.
Nocardia, flavonoid, microbial metabolism, Beauveria bassiana, Aspergillus alliaceus
NCBI PubMed ID: 16508185Publication DOI: 10.1248/cpb.54.320Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Khan IA
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, FTIR, UV, extraction, CC, HR-ESI-MS
The publication contains the following compound(s):
- Compound ID: 18510
|
b-D-Glcp4Me-(1-7)-Subst
Subst = 7-hydroxyflavone = SMILES O=C1C=C(OC2=C1C=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
; 413.1267 [M-H]+
C22H22O8
- Compound ID: 18511
|
b-D-Glcp4Me-(1-7)-Subst
Subst = 7,4'-dihydroxyflavone = SMILES O=C1C=C(C2=CC={54}C(O)C=C2)OC3=C1C=C{7}C(O)=C3 |
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Structure type: monomer
; 429.1212 [M-H]+
C22H22O9
- Compound ID: 18509
|
b-D-Glcp4Me-(1-3)-Subst
Subst = flavonol = SMILES O=C1{3}C(O)=C(OC2=C1C=CC=C2)C3=CC=CC=C3 |
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Structure type: monomer
; 415.1364 [M+H]+
C22H22O8
- Compound ID: 18512
|
b-D-Glcp4Me-(1-2)-Subst
Subst = 1-(2-hydroxyphenyl)-3-phenylpropane-1,2-diol = SMILES O{52}C1=C(C=CC=C1){1}C(O){2}C(O)CC2=CC=CC=C2 |
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Structure type: monomer
; 421.2331 [M+H]+
C22H28O8
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