The recently discovered antibiotic burnettramic acid A (1) and three new congeners, burnettramic acids C-E (2-4), were identified from the co-cultures of two marine Aspergillus strains. The structure of burnettramic acid A was revised on the basis of reinterpretation of the nuclear magnetic resonance (NMR) data and chemical derivatization. The full absolute configurations of burnettramic acids were established using the Mosher ester method and Marfey's analysis, combined with density functional theory calculation of NMR and electric circular dichroism data.

NMR, absolute configuration, Aspergillus, burnettramic acids

• Compound ID: 22317
  

  b-D-Manp-(1-34)-Subst Subst = burnettramic acid A aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCCCC/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O

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  Structure type: monomer ; 770.5055 [M+H]+, 792.4851 [M+Na]+
  C41H71NO12
  Trivial name: burnettramic acid A
  Compound class: glycoside
  Reference(s) to other database(s): GenDB:MN294469
  
   
  
  Aspergillus versicolor IMB17−055, Aspergillus chevalieri IMB18−208
  CSDB ID 50388 (all data & tools)
• Compound ID: 22318
  

  b-D-Manp-(1-34)-Subst Subst = burnettramic acid C aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(CCCN2C\1=O)[H])=O)C)CCCCCCC/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O

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  Structure type: monomer ; 754.5102 [M+H]+, 776.4898 [M+Na]+
  C41H71NO11
  Trivial name: burnettramic acid C
  Compound class: glycoside
  Reference(s) to other database(s): GenDB:MN294469
  
   
  
  Aspergillus versicolor IMB17−055, Aspergillus chevalieri IMB18−208
  CSDB ID 50389 (all data & tools)
• Compound ID: 22319
  

  b-D-Manp-(1-34)-Subst Subst = burnettramic acid D aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCC/C=C/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O

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  Structure type: monomer ; 768.4890 [M+H]+, 790.4727 [M+Na]+
  C41H69NO12
  Trivial name: burnettramic acid D
  Compound class: glycoside
  Reference(s) to other database(s): GenDB:MN294469
  
   
  
  Aspergillus versicolor IMB17−055, Aspergillus chevalieri IMB18−208
  CSDB ID 50390 (all data & tools)
• Compound ID: 22320
  

  b-D-Manp-(1-34)-Subst Subst = burnettramic acid E aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCCCCCCC{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O

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  Structure type: monomer ; 772.5210 [M+H]+, 794.5015 [M+Na]+
  C41H73NO12
  Trivial name: burnettramic acid E
  Compound class: glycoside
  Reference(s) to other database(s): GenDB:MN294469
  
   
  
  Aspergillus versicolor IMB17−055, Aspergillus chevalieri IMB18−208
  CSDB ID 50391 (all data & tools)