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1. (Article ID: 7984)
Tronina T, Bartmańska A, Milczarek M, Wietrzyk J, Popłoński J, Rój E, Huszcza E
Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol
Bioorganic and Medicinal Chemistry Letters 23(7) (2013)
1957-1960
The biotransformation of xanthohumol (1), a prenylated chalcone isolated from hops by selected fungi, was investigated. Microbial regioselective glycosylation at the C-4' position led to xanthohumol 4'-O-β-D-glucopyranoside (2) and xanthohumol 4'-O-β-D-(4'''-O-methyl)-glucopyranoside (3). The subsequent cyclization of 2 resulted in isoxanthohumol 7-O-β-glucopyranoside (4). The structures of the products were identified based on spectroscopic methods. The biological activity of isolated metabolites has been evaluated. Compared to xanthohumol (1), metabolite 2 is a better 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenger, while 2 and 3 have stronger antiproliferative activity against the human HT-29 colon cancer cell line.
glycosylation, Antioxidant activity, Antiproliferative activity, biotransformation, xanthohumol, spent hops
NCBI PubMed ID: 23466227Publication DOI: 10.1016/j.bmcl.2013.02.031Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: tomasz.tronina

up.wroc.pl
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Department of Experimental Oncology, Wrocław, Poland, Fertilizer Research Institute, Supercritical Extraction Department, Puławy, Poland
Methods: 13C NMR, 1H NMR, HPLC, cell growth, anticancer activity assay, radical scavenging assay
The publication contains the following compound(s):
- Compound ID: 20042
|
b-D-Glcp-(1-4')-Subst
Subst = xanthohumol = SMILES C/C(C)=C\CC1={52}C(O)C(C(/C=C/C2=CC={54}C(C=C2)O)=O)=C(OC)C={4}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 20043
|
b-D-Glcp4Me-(1-4')-Subst
Subst = xanthohumol = SMILES C/C(C)=C\CC1={52}C(O)C(C(/C=C/C2=CC={54}C(C=C2)O)=O)=C(OC)C={4}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 20044
|
b-D-Glcp-(1-7)-Subst
Subst = isoxanthohumol = SMILES C/C(C)=C\CC1=C2C(C(CC(C3=CC={54}C(O)C=C3)O2)=O)=C(OC)C={7}C1O |
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Structure type: monomer
Compound class: glycoside
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2. (Article ID: 8631)
Sordon S, Popłoński J, Huszcza E
Microbial glycosylation of flavonoids
Polish Journal of Microbiology 65(2) (2016)
137-151
Flavonoids constitute a large group of polyphenolic compounds naturally found in plants, which have a wide range of biological activity. Although flavonoids are beneficial to human health, their application is limited by their low bioavailability and poor water-solubility. Therefore, recently there has been a particular interest in glycosylated forms of flavonoids, which usually are better soluble, more stable, and more functional compared to their aglycones. Microbial transformation of natural flavonoids may be an attractive way of receiving their glycosylated derivatives in amounts sufficient for the research on the effect of glycoside group on compound properties and for further application of these compounds as ingredients of dietary supplements and pharmaceuticals.
glycosides, biotransformation, microbial glycosylation, flavonoids
NCBI PubMed ID: 28517915Journal NLM ID: 101229003Publisher: Polskie Towarzystwo Mikrobiologow
Correspondence: sandra.sordon

up.wroc.pl
Institutions: Faculty of Food Science, Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
The publication contains the following compound(s):
- Compound ID: 21438
Structure type: monomer
Trivial name: isoquercitrin
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Reference(s) to other database(s): CCSD:
49965, CBank-STR:953
- Compound ID: 21246
Structure type: monomer
Compound class: glucoside, glycoside
- Compound ID: 21435
|
b-D-Glcp4Me-(1-7)-Subst-(5-1)-Me
Subst = flavaprenin = SMILES C/C(C)=C\CC1={7}C(O)C={5}C(O)C2=C1O[C@@H](CC2=O)C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21437
|
b-D-Glcp4Me-(1-7)-Subst
Subst = flavaprenin = SMILES C/C(C)=C\CC1={7}C(O)C={5}C(O)C2=C1O[C@@H](CC2=O)C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21439
|
/Variants 0/-b-D-Glcp
/Variants 0/ is:
Kaempferol-(3-1)-
OR (exclusively)
Subst-(3-1)-
Subst = morin = SMILES O=C1{3}C(O)=C(OC2=C1{5}C(O)=C{7}C(O)=C2)C3={52}C(O)C={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21440
|
b-D-Glcp-(1-7)-Subst
Subst = kurarinone = SMILES C=C(C)C(C/C=C(C)\C)C(C)C1={7}C(O)C=C(OC)C2=C1O[C@@H](CC2=O)C3=CC={54}C(O)C={52}C3O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 20042
|
b-D-Glcp-(1-4')-Subst
Subst = xanthohumol = SMILES C/C(C)=C\CC1={52}C(O)C(C(/C=C/C2=CC={54}C(C=C2)O)=O)=C(OC)C={4}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 20043
|
b-D-Glcp4Me-(1-4')-Subst
Subst = xanthohumol = SMILES C/C(C)=C\CC1={52}C(O)C(C(/C=C/C2=CC={54}C(C=C2)O)=O)=C(OC)C={4}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21434
|
b-D-Glcp-(1-7)-Subst-(5-1)-Me
Subst = flavaprenin = SMILES C/C(C)=C\CC1={7}C(O)C={5}C(O)C2=C1O[C@@H](CC2=O)C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21436
|
b-D-Glcp-(1-7)-Subst
Subst = flavaprenin = SMILES C/C(C)=C\CC1={7}C(O)C={5}C(O)C2=C1O[C@@H](CC2=O)C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21441
|
/Variants 0/-+
|
b-D-Glcp-(1-7)-Subst
/Variants 0/ is:
?%b-D-Glcp-(1-4')-
OR (exclusively)
?%S-3')-
Subst = isoangustone A = SMILES C/C(C)=C\CC1=CC(C2=COC3=C(C2=O){5}C(O)=C(C/C=C(C)\C){7}C(O)=C3)=C{53}C(O)={54}C1O |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 21442
|
/Variants 0/-b-D-Glcp
/Variants 0/ is:
Subst-(7-1)-
OR (exclusively)
Subst-(3-1)-
Subst = silybin A = SMILES COC1=CC([C@H]2OC3=CC([C@@H]4OC5=C{7}C(O)=C{5}C(O)=C5C({3}[C@H]4O)=O)=CC=C3O[C@@H]2{59}CO)=CC={104}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21443
|
/Variants 0/-b-D-Glcp
/Variants 0/ is:
Subst-(7-1)-
OR (exclusively)
Subst-(3-1)-
Subst = silybin B = SMILES COC1=CC([C@@H]2OC3=CC([C@@H]4OC5=C{7}C(O)=C{5}C(O)=C5C({3}[C@H]4O)=O)=CC=C3O[C@H]2{59}CO)=CC={104}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 21444
|
L-Rhap-(1-4')-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
Compound class: glycoside
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