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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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2. (Article ID: 8154)
Herath W, Khan SI, Khan IA
Microbial metabolism. Part 14. Isolation and bioactivity evaluation of microbial metabolites of resveratrol
Natural Product Research 27(16) (2013)
1437-1444
The fungi, Beauveria bassiana (ATCC 13144) and Penicillium chrysogenium (ATCC 9480) transformed resveratrol to resveratrol-3-O-sulphate. The former, in addition, gave 5-methoxyresveratrol-3-O-β-glucoside with the latter yielding 5-methoxyresveratrol-3-O-sulphate. The structures were established by spectroscopic methods. Evaluation of biological activity of metabolites through a series of mammalian cell based assays indicated that resveratrol tends to lose its anti-inflammatory, cytotoxic and anti-oxidant activities with the substitution of its hydroxyl groups.
resveratrol, microbial metabolism, Beauveria bassiana, Penicillium chrysogenium
NCBI PubMed ID: 22950854Publication DOI: 10.1080/14786419.2012.722089Journal NLM ID: 101167924Publisher: Milton Park, UK : Taylor & Francis Health Sciences
Correspondence: Khan IA
olemiss.edu>
Institutions: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, MS, USA, Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, MS, USA
Methods: 13C NMR, 1H NMR, IR, TLC, UV, HR-ESI-MS, HMBC
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