Secofumitremorgins C and D, a pair of atropisomers from saltern-derived fungus Aspergillus fumigatus GXIMD00544

J Asian Nat Prod Res. 2024 Sep;26(9):1049-1056. doi: 10.1080/10286020.2024.2349664. Epub 2024 May 16.

Abstract

A pair of atropisomers secofumitremorgins C (1a) and D (1b), together with fifteen known alkaloids (2-16), were isolated from a saltern-derived fungus Aspergillus fumigatus GXIMD00544. The structures of atropisomers 1a and 1b were elucidated by the detailed spectroscopic data, chemical reaction and quantum chemical calculations. Compounds 1 and 8 displayed antifungal spore germination effects against plant pathogenic fungus associated with sugarcane Fusarium sp. with inhibitory rates of 53% and 77% at the concentration of 100 µM, repectively. Atropisomers 1 also exhibited antifouling potential against Balanus amphitrite larval settlement with an inhibitory rate of 96% at the concentration of 100 µM.

Keywords: Saltern-derived fungus; alkaloids; antifouling; atropisomers; fungal spore germination.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Animals
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Aspergillus fumigatus* / drug effects
  • Fusarium / chemistry
  • Larva
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Stereoisomerism
  • Thoracica / drug effects

Substances

  • Antifungal Agents
  • Alkaloids