An antimicrobial diketopiperazine alkaloid and co-metabolites from an endophytic strain of Gliocladium isolated from Strychnos cf. toxifera

Nat Prod Res. 2012 Nov;26(21):2013-9. doi: 10.1080/14786419.2011.639070. Epub 2011 Nov 25.

Abstract

From an endophytic strain of Gliocladium sp. isolated from the Amazonian plant Strychnos cf. toxifera, we obtained the diketopiperazine alkaloid cyclo-(glycyl-L-tyrosyl)-4,4-dimethylallyl ether (1), the steroids ergosterol (2), ergosterol peroxide (3), cerevisterol (4) and the citric acid (5). The AcOEt extract of the fermented broth by Gliocladium sp. showed potent activity against the cancer cell lines MDA-MB435 (human breast cancer cells), HCT-8 (human colorectal cancer cells) and SF-295 (human glioblastoma cancer cells). Compound 1 exhibited a strong antimicrobial activity against Micrococcus luteus at a concentration of 43.4 µM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor / drug effects
  • Citric Acid / isolation & purification
  • Diketopiperazines / chemistry*
  • Diketopiperazines / isolation & purification
  • Dose-Response Relationship, Drug
  • Endophytes / chemistry
  • Ergosterol / analogs & derivatives
  • Ergosterol / isolation & purification
  • Gliocladium / chemistry*
  • Gliocladium / isolation & purification
  • Humans
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Phytosterols / isolation & purification
  • Strychnos / microbiology*

Substances

  • Alkaloids
  • Anti-Infective Agents
  • Antineoplastic Agents
  • Diketopiperazines
  • Peptides, Cyclic
  • Phytosterols
  • cyclo-(glycyl-L-tyrosyl)-4,4-dimethylallyl ether
  • Citric Acid
  • cerevisterol
  • ergosterol-5,8-peroxide
  • Ergosterol