Harvestman phenols and benzoquinones: characterisation and biosynthetic pathway

Molecules. 2013 Sep 16;18(9):11429-51. doi: 10.3390/molecules180911429.

Abstract

Benzoquinones are usually present in arthropod defence exudates. Here, we describe the chemical profiles of 12 harvestman species belonging to the neotropical family Gonyleptidae. Nine of the studied species produced benzoquinones, while three produced alkyl phenols. Two benzoquinones and one phenol exhibited biological activity against bacteria and fungi. We also studied the biosynthesis of 2-ethyl-1,4-benzoquinone by feeding Magnispina neptunus individuals with ¹³C-labelled precursors; the benzoquinones were biosynthesised through a polyketide pathway using acetate and propionate building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology
  • Arachnida / chemistry
  • Arachnida / metabolism*
  • Bacillus / drug effects
  • Benzoquinones / chemistry*
  • Benzoquinones / metabolism
  • Benzoquinones / pharmacology
  • Biosynthetic Pathways
  • Candida albicans / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Structure
  • Phenols / chemistry*
  • Phenols / metabolism
  • Phenols / pharmacology
  • Pseudomonas aeruginosa / drug effects

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzoquinones
  • Phenols