In order to search for structurally novel and bioactive natural compounds from marine-derived fungi, a halotolerant fungal strain (THW-18) identified as Alternaria raphani was isolated from sediment collected in the Hongdao sea salt field. From the ethyl acetate extract of Alternaria raphani, three new cerebrosides, alternarosides A-C (1-3), and a new diketopiperazine alkaloid, alternarosin A (4), together with 15 known compounds were isolated and identified by spectroscopic and chemical methods, as well as X-ray crystal diffraction analysis. Compounds 1-4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and Candida albicans with MIC values ranging from 70 to 400 muM.

cerebroside

NCBI PubMed ID: 19685913
Publication DOI: 10.1021/np9002299
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Correspondence: weimingzhuouc.edu.cn
Institutions: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS/MS, NMR-1D, methanolysis, extraction, optical rotation measurement, CC, HR-ESI-MS
 

• Compound ID: 18429
  

  b-D-Glcp-(1-1)-+ | R-2HOC18={t3}-(1-2)-Subst Subst = (2S,3R,4E)-2-amino-1,3-dihydroxy-9-methylene-4-octadecen-8-one = SMILES C=C(CCCCCCCCC)C(=O)CC/C=C/{3}[C@@H](O){2}[C@@H](N){1}CO

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  Structure type: monomer ; 768.6 [M+H]+
  C43H78NO10
  Trivial name: alternaroside A
  Compound class: glycosphingolipid, cerebroside
  
   
  
  Alternaria raphani THW-18
  CSDB ID 42258 (all data & tools)
• Compound ID: 18430
  

  b-D-Glcp-(1-1)-+ | R-2HOC18={t3}-(1-2)-S,R-9b1SphdC18

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  Structure type: monomer ; 740.6 [M+H]+
  C42H77NO9
  Trivial name: alternaroside B
  Compound class: glycosphingolipid, cerebroside
  
   
  
  Alternaria raphani THW-18
  CSDB ID 42259 (all data & tools)
• Compound ID: 18431
  

  b-D-Glcp-(1-1)-+ | R-2HOC18={t3}-(1-2)-Subst Subst = (2S,3R,4E,8Z)-2-aminooctadeca-4,8-diene-1,3-diol = SMILES CCCCCCCCC/C=C\CC/C=C/{3}[C@@H](O){2}[C@@H](N){1}CO

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  Structure type: monomer ; 740.6 [M+H]+
  C42H78NO9
  Trivial name: alternaroside C
  Compound class: glycosphingolipid, cerebroside
  
   
  
  Alternaria raphani THW-18
  CSDB ID 42260 (all data & tools)
• Compound ID: 18432
  

  b-D-Glcp-(1-1)-+ | R-2HOC18={t3}-(1-2)-S,R-9b1SphdC19

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  Structure type: monomer ; 754.8 [M+H]+
  C43H77NO10
  Trivial name: cerebroside C
  Compound class: glycosphingolipid, cerebroside
  
   
  
  Alternaria raphani THW-18
  CSDB ID 42261 (all data & tools)