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Molecules 2013, 18(9), 11429-11451; doi:10.3390/molecules180911429
Article

Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

1, 1, 1, 2, 3 and 1,*
1 Instituto de Química, Universidade Estadual de Campinas, C.P. 6154, 13083-970 Campinas, SP, Brasil 2 Laboratório de Química Bio-Orgânica, Departamento de Química, Universidade Federal de São Carlos, Caixa Postal 676, 13565-905 São Carlos, SP, Brasil 3 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 / Revised: 5 September 2013 / Accepted: 6 September 2013 / Published: 16 September 2013
(This article belongs to the Section Metabolites)
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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 chemical defence; NMR spectroscopy; arthropod biosynthesis; labelled precursors; evolution; chemotaxonomy; Opiliones
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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