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1. (Article ID: 8632)
Sordon S, Popłoński J, Tronina T, Huszcza E
Microbial glycosylation of daidzein, genistein and biochanin A: two new glucosides of biochanin A
Molecules 22(1) (2017)
E81 (1-9)
Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.
fungi, genistein, microbial glycosylation, daidzein, biochanin A, isoflavones
NCBI PubMed ID: 28054950Publication DOI: 10.3390/molecules22010081Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Popłoński J
up.wroc.pl>; Tronina T up.wroc.pl>; Huszcza E up.wroc.pl>; Sordon S wp.pl>
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland, Department of Chemistry,Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, TLC, HPLC, CC, HR-ESI-MS, HMBC, COSY, HSQC
The publication contains the following compound(s):
- Compound ID: 19776
|
b-D-Glcp4Me-(1-7)-Subst
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 19777
|
b-D-Glcp4Me-(1-7)-Subst
Subst = daidzein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1C=C{7}C(O)={8}C3 |
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Structure type: monomer
Trivial name: daidzin
Compound class: glycoside
- Compound ID: 21471
|
b-D-Glcp4Me-(1-7)-Subst-(4'-1)-Me
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
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Structure type: monomer
; 459.1297 [M-H]-
Compound class: glycoside
- Compound ID: 21445
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b-D-Glcp-(1-7)-Subst
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
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Structure type: monomer
Trivial name: genistin, genistein glucoside
Compound class: glycoside, flavonoid glycoside
Reference(s) to other database(s): CCSD:
48436, CBank-STR:1217
- Compound ID: 21446
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b-D-Glcp-(1-7)-Subst4'Me
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
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Structure type: monomer
; 445.1151 [M-H]-
C22H22O10
Trivial name: sissotrin
Compound class: glycoside
- Compound ID: 21447
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b-D-Glcp-(1-5)-Subst4'Me
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
Show graphically |
Structure type: monomer
; 445.1151 [M-H]-
C22H22O10
Trivial name: isosissotrin
Compound class: glycoside
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