Incubation of spirolaxine 1a with the fungus Absidia cuneospora afforded 5β-glucosyl-spirolaxine 2b; the structure of the biotransformed product was deduced on the basis of MS, NMR data and chemical semi-synthesis. When using Trametes hirsuta as a bioagent 1a afforded 5β-xylosyl-spirolaxine 3a; the identification of the sugar moiety came from acidic hydrolysis of the new metabolite.

semi-synthesis, biotransformation, fungal metabolites, spirolaxine, glycosyl and xylosyl derivative

Publication DOI: 10.1016/j.molcatb.2012.06.006
Journal NLM ID: 9602616
Publisher: Amsterdam: Elsevier
Correspondence: gianluca.nasinipolimi.it
Institutions: CNR-ICRM, Dipartimento di Chimica, Materiali ed Ingegneria Chimica del Politecnico, Milano, Italy
Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, MS, HPLC, UV, extraction, optical rotation measurement, acetylation, HPTLC, CC, HMBC, COSY, HSQC
 

• Compound ID: 18797
  

  b-D-Glcp-(1-5)-Subst Subst = spirolaxine = SMILES COC1=C(C(O[C@@H]2CCCCC[C@@H]3CCC[C@@]4(O3)CC[C@@H](O4)C)=O)C2=C{5}C(O)=C1

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  Structure type: monomer ; 567 [M+H]+
  Compound class: glycoside
  
   
  
  Absidia cuneospora ATCC 24693
  CSDB ID 43851 (all data & tools)
• Compound ID: 18798
  

  b-D-Xylp-(1-5)-Subst Subst = spirolaxine = SMILES COC1=C(C(O[C@@H]2CCCCC[C@@H]3CCC[C@@]4(O3)CC[C@@H](O4)C)=O)C2=C{5}C(O)=C1

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  Structure type: monomer ; 537 [M+H]+; 559 [M+Na]+
  Compound class: glycoside
  
   
  
  Trametes hirsuta sp. ICRM 197
  CSDB ID 43852 (all data & tools)
• Compound ID: 18799
  

  b-D-Xylp2Ac3Ac4Ac-(1-5)-Subst Subst = spirolaxine = SMILES COC1=C(C(O[C@@H]2CCCCC[C@@H]3CCC[C@@]4(O3)CC[C@@H](O4)C)=O)C2=C{5}C(O)=C1

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  Structure type: monomer ; 663 [M+H]+; 685 [M+Na]+
  Compound class: glycoside
  
   
  
  Trametes hirsuta sp. ICRM 197
  CSDB ID 43853 (all data & tools)