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Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway
Instituto de Química, Universidade Estadual de Campinas, C.P. 6154, 13083-970 Campinas, SP, Brasil
Laboratório de Química Bio-Orgânica, Departamento de Química, Universidade Federal de São Carlos, Caixa Postal 676, 13565-905 São Carlos, SP, Brasil
Departamento de Ecologia, Instituto de Biociências, Universidade de São Paulo, Rua do Matão, trav.14, no. 321, 05508-090 São Paulo, SP, Brasil
* Author to whom correspondence should be addressed.
Received: 19 July 2013; in revised form: 5 September 2013 / Accepted: 6 September 2013 / Published: 16 September 2013
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
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Rocha, D.F.O.; Wouters, F.C.; Zampieri, D.S.; Brocksom, T.J.; Machado, G.; Marsaioli, A.J. Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway. Molecules 2013, 18, 11429-11451.
Rocha DFO, Wouters FC, Zampieri DS, Brocksom TJ, Machado G, Marsaioli AJ. Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway. Molecules. 2013; 18(9):11429-11451.
Rocha, Daniele F.O.; Wouters, Felipe C.; Zampieri, Dávila S.; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J. 2013. "Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway." Molecules 18, no. 9: 11429-11451.