Trichopeptides A and B, trichocyclodipeptides A-C, new peptides from the ascomycete fungus Stagonospora trichophoricola

J Antibiot (Tokyo). 2017 Aug;70(9):923-928. doi: 10.1038/ja.2017.76. Epub 2017 Jul 5.

Abstract

Trichopeptides A (1) and B (2), new linear tetrapeptide and tripeptide, respectively, and three new diketopiperazines trichocyclodipeptides A-C (3-5) were isolated from the fermentation of the ascomycete fungus Stagonospora trichophoricola, a fungus isolated from the soil sample surrounding the fruiting body of Ophiocordyceps sinensis in Maqin Country, Qinghai Province, People's Republic of China. Their structures were primarily elucidated by interpretation of NMR and MS experiments. The absolute configurations of 1-5 were assigned through Marfey's method on their acid hydrolyzates. Compound 3 showed antifungal activity against Candida albicans with the IC50 and MIC values of 22 and 90 μg ml-1, respectively.

MeSH terms

  • A549 Cells
  • Adenocarcinoma, Bronchiolo-Alveolar / drug therapy
  • Amino Acid Sequence
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / isolation & purification*
  • Antibiotics, Antineoplastic / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Antimicrobial Cationic Peptides / chemistry
  • Antimicrobial Cationic Peptides / isolation & purification*
  • Antimicrobial Cationic Peptides / pharmacology
  • Ascomycota / metabolism*
  • Bacillus subtilis / drug effects
  • Bacillus subtilis / growth & development
  • Candida albicans / drug effects
  • Candida albicans / growth & development
  • Cell Survival / drug effects
  • Drug Discovery*
  • Escherichia coli / drug effects
  • Escherichia coli / growth & development
  • Fermentation
  • Humans
  • Inhibitory Concentration 50
  • K562 Cells
  • Leukemia, Erythroblastic, Acute / drug therapy
  • Microbial Sensitivity Tests
  • Oligopeptides / chemistry
  • Oligopeptides / isolation & purification
  • Oligopeptides / pharmacology
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / growth & development
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Antibiotics, Antineoplastic
  • Antifungal Agents
  • Antimicrobial Cationic Peptides
  • Oligopeptides
  • trichocyclodipeptide A
  • trichocyclodipeptide B
  • trichocyclodipeptide C
  • trichopeptide A
  • trichopeptide B