Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• 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: 23466227
  Publication DOI: 10.1016/j.bmcl.2013.02.031
  Journal NLM ID: 9107377
  Publisher: 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
  
   
  
  Mortierella mutabilis AM404
  CSDB ID 45446 (all data & tools)
• Article ID: 8276
  Bartmańska A, Huszcza E, Tronina T "Transformation of isoxanthohumol by fungi" - Journal of Molecular Catalysis B: Enzymatic 61(3-4) (2009) 221-224
  

  Isoxanthohumol is the most abundant and an important prenylated flavonoid present in hopped beers. In order to select microorganisms capable of transforming isoxanthohumol screening tests on 44 fungi cultures were performed. This kind of activity has not been previously examined. Beauveria bassiana AM278 and Absidia glauca AM177 converted isoxanthohumol into glucoside derivatives, whereas Fusarium equiseti AM15 transformed it into (2R)-2″-(2″′-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8]-4′-hydroxy-5-methoxyflavanone with high efficiency. Isoxanthohumol 7-O-β-D-4″′-methoxyglucopyranoside is a new compound.

  biotransformation, Beauveria bassiana, Fusarium equiseti, isoxanthohumol, Absidia glauca

  Publication DOI: 10.1271/bbb.65.2384
  Journal NLM ID: 9602616
  Publisher: Amsterdam: Elsevier
  Correspondence: Bartmańska A ; Huszcza E ; Tronina T
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, UV, extraction, optical rotation measurement, CD, CC
  
   
  
  Absidia glauca AM177
  CSDB ID 46663 (all data & tools)
• Article ID: 9099
  Bartmańska A, Tronina T, Popłoński J "Biotransformation of a major beer prenylflavonoid – isoxanthohumol" - Zeitschrift für Naturforschung. C, Journal of Biosciences 74(1-2) (2019) 1-7
  

  Microbial transformations of isoxanthohumol (1), a beer prenylated flavonoid, by 51 fungi were investigated. Many of the tested fungi cultures were capable of effective transformation of 1. Mucor hiemalis and Fusarium oxysporum converted isoxanthohumol (1) into isoxanthohumol 7-O-β-D-glucopyranoside (3) and (2R)-2″-(2″'-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8]-4″,5-hydroxy-5-methoxyflavanone (4), respectively. No product was obtained in the transformation of 1 by Absidia glauca conducted in a phosphate buffer. In the same medium, Beauveria bassiana converted isoxanthohumol (1) to isoxanthohumol 7-O-β-D-4″'-O-methylglucopyranoside (2).

  Mucor hiemalis, Fusarium oxysporum, Beauveria bassiana, isoxanthohumol, Absidia glauca

  NCBI PubMed ID: 30864390
  Publication DOI: 10.1515/znc-2018-0101
  Journal NLM ID: 8912155
  Publisher: Verlag der Zeitschrift für Naturforschung
  Correspondence: agnieszka.bartmanska@upwr.edu.pl
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, UV, biosynthetic methods, CD, cell growth
  
   
  
  Mucor hiemalis AM450, Fusarium oxysporum AM13
  CSDB ID 50159 (all data & tools)

Show legend Show as text

Structure type: monomer ; 531 [M+H]+
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8276
  Bartmańska A, Huszcza E, Tronina T "Transformation of isoxanthohumol by fungi" - Journal of Molecular Catalysis B: Enzymatic 61(3-4) (2009) 221-224
  

  Isoxanthohumol is the most abundant and an important prenylated flavonoid present in hopped beers. In order to select microorganisms capable of transforming isoxanthohumol screening tests on 44 fungi cultures were performed. This kind of activity has not been previously examined. Beauveria bassiana AM278 and Absidia glauca AM177 converted isoxanthohumol into glucoside derivatives, whereas Fusarium equiseti AM15 transformed it into (2R)-2″-(2″′-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8]-4′-hydroxy-5-methoxyflavanone with high efficiency. Isoxanthohumol 7-O-β-D-4″′-methoxyglucopyranoside is a new compound.

  biotransformation, Beauveria bassiana, Fusarium equiseti, isoxanthohumol, Absidia glauca

  Publication DOI: 10.1271/bbb.65.2384
  Journal NLM ID: 9602616
  Publisher: Amsterdam: Elsevier
  Correspondence: Bartmańska A ; Huszcza E ; Tronina T
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, UV, extraction, optical rotation measurement, CD, CC
  
   
  
  Beauveria bassiana AM278
  CSDB ID 46664 (all data & tools)
• Article ID: 9099
  Bartmańska A, Tronina T, Popłoński J "Biotransformation of a major beer prenylflavonoid – isoxanthohumol" - Zeitschrift für Naturforschung. C, Journal of Biosciences 74(1-2) (2019) 1-7
  

  Microbial transformations of isoxanthohumol (1), a beer prenylated flavonoid, by 51 fungi were investigated. Many of the tested fungi cultures were capable of effective transformation of 1. Mucor hiemalis and Fusarium oxysporum converted isoxanthohumol (1) into isoxanthohumol 7-O-β-D-glucopyranoside (3) and (2R)-2″-(2″'-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8]-4″,5-hydroxy-5-methoxyflavanone (4), respectively. No product was obtained in the transformation of 1 by Absidia glauca conducted in a phosphate buffer. In the same medium, Beauveria bassiana converted isoxanthohumol (1) to isoxanthohumol 7-O-β-D-4″'-O-methylglucopyranoside (2).

  Mucor hiemalis, Fusarium oxysporum, Beauveria bassiana, isoxanthohumol, Absidia glauca

  NCBI PubMed ID: 30864390
  Publication DOI: 10.1515/znc-2018-0101
  Journal NLM ID: 8912155
  Publisher: Verlag der Zeitschrift für Naturforschung
  Correspondence: agnieszka.bartmanska@upwr.edu.pl
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, UV, biosynthetic methods, CD, cell growth
  
   
  
  Beauveria bassiana AM278
  CSDB ID 50158 (all data & tools)