Antifungal trichothecene sesquiterpenes obtained from the culture broth of marine-derived Trichoderma cf. brevicompactum and their structure-activity relationship

Bioorg Med Chem Lett. 2020 Sep 1;30(17):127375. doi: 10.1016/j.bmcl.2020.127375. Epub 2020 Jul 4.

Abstract

Two new trichothecene sesquiterpenes, trichobreols D (1) and E (2), were isolated from the culture broth of marine-derived Trichoderma cf. brevicompactum together with trichobreol A (3). The structures of 1 and 2 were assigned on the basis of their spectroscopic data. Compound 1 inhibited the growth of two yeast-like fungi, Candida albicans and Cryptococcus neoformans, with equivalent MIC values (6.3 μg/mL), while 2 gave MIC values of 12.5 and 25 μg/mL, respectively. The antifungal activities of five semisynthetic derivatives (4-8) prepared from 3 were evaluated and compared to investigate the preliminary structure-activity relationship.

Keywords: Antifungal activity; Candida albicans; Cryptococcus neoformans; Trichobreol; Trichoderma cf. brevicompactum; Trichothecene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Candida albicans / drug effects
  • Cryptococcus neoformans / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Rhodophyta / microbiology
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Structure-Activity Relationship
  • Trichoderma / chemistry*
  • Trichoderma / metabolism
  • Trichothecenes / chemistry*
  • Trichothecenes / isolation & purification
  • Trichothecenes / pharmacology

Substances

  • Antifungal Agents
  • Sesquiterpenes
  • Trichothecenes
  • trichothecene