Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

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.

Keywords

• chemical defence
• NMR spectroscopy
• arthropod biosynthesis
• labelled precursors
• evolution
• chemotaxonomy
• Opiliones