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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
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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
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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 |
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Structure type: monomer
; 445.1151 [M-H]-
C22H22O10
Trivial name: isosissotrin
Compound class: glycoside
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2. (Article ID: 8898)
Sordon S, Popłoński J, Tronina T, Huszcza E
Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca
Bioorganic Chemistry 93 (2019)
ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
upwr.edu.pl>; Popłoński J upwr.edu.pl>; Tronina T upwr.edu.pl>; Huszcza E upwr.edu.pl>
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
The publication contains the following compound(s):
- Compound ID: 18499
|
b-D-Glcp4Me-(1-7)-Subst
Subst = chrysin = SMILES O=C1C=C(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
C22H22O9
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21970
Structure type: monomer
; 445.1138 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21971
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b-D-Glcp4Me-(1-7)-Subst
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
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Structure type: monomer
; 461.1087 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21972
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b-D-Glcp4Me-(1-7)-Subst4'Me
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
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Structure type: monomer
; 475.1234 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21973
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b-D-Glcp4Me-(1-3')-Subst4'Me
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
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Structure type: monomer
; 475.1234 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21974
|
b-D-Glcp4Me-(1-7)-Subst
Subst = pinocembrin = SMILES O=C1CC(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
; 431.1345 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21975
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b-D-Glcp4Me-(1-7)-Subst
Subst = naringenin = SMILES O=C1CC(C2=CC={54}C(O)C=C2)OC3=C{7}C(O)={6}C{5}C(O)=C13 |
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Structure type: monomer
; 447.1292 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21976
|
b-D-Glcp4Me-(1-7)-Subst
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
; 463.1245 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21977
|
b-D-Glcp4Me-(1-7)-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
; 477.1401 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21978
|
b-D-Glcp4Me-(1-3')-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
; 477.1401 [M-H]-
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21986
|
b-D-Glcp-(1-3')-Subst4'Me
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21410
|
b-D-Glcp-(1-7)-Subst
Subst = naringenin = SMILES O=C1CC(C2=CC={54}C(O)C=C2)OC3=C{7}C(O)={6}C{5}C(O)=C13 |
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Structure type: monomer
Trivial name: prunin
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21981
|
b-D-Glcp-(1-7)-Subst
Subst = chrysin = SMILES O=C1C=C(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21982
Structure type: monomer
Trivial name: cosmosiin, apigenin 7-O-glucoside, rhoifolin, apigenin 7-glucoside, apigetrin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
50502, CBank-STR:1305
- Compound ID: 21983
|
b-D-Glcp-(1-7)-Subst
Subst = pinocembrin = SMILES O=C1CC(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21984
|
b-D-Glcp-(1-7)-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21985
|
b-D-Glcp-(1-3')-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21979
|
b-D-Glcp-(1-3')-Subst
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 21980
|
b-D-Glcp-(1-7)-Subst
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
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