Production of Oosporein and Related Bibenzoquinone Analogues in Arcopilus amazonicus Revealed by Genome Mining and Mass Spectrometry Analysis
Oosporein (OOS) is the major specialized metabolite produced by the fungus Arcopilus amazonicus, an endophyte from Paullinia cupana. Genes related to the biosynthesis of this molecule in A. amazonicus diverge from those found in Beauveria bassiana. Furthermore, high-resolution liquid chromatography coupled with mass spectrometry combined with molecular networking, revealed the production of analogous compounds with varying degrees of oxygenation. Based on these analytical data, the analogues were annotated as phoenicin diquinol (2), phoenicin quinol (4) and phoenicin (5). By combining mass spectrometry and genome mining, a comprehensive biosynthetic pathway is proposed for these compounds, including the feasibility of a novel putative biphenol oxidation pathway mediated by the monooxygenase gene AAm15, which is exclusive to A. amazonicus. Additionally, the production of OOS, 2, 4 and 5 by a single fungal species is reported for the first time.
Authors
- Aline Moreira Rodrigues (ORCID: https://orcid.org/0009-0009-0451-0300)
- Thiago Fernandes Sousa
- Aline O. dos Santos (ORCID: https://orcid.org/0000-0001-7818-3263)
- Gilvan Ferreira da Silva (ORCID: https://orcid.org/0000-0003-2828-8299)
- Lívia Soman de Medeiros (ORCID: https://orcid.org/0000-0001-8743-3340)
- Renan Galaverna (ORCID: https://orcid.org/0000-0002-5035-7660)
- M. E. B. Yamagishi (ORCID: https://orcid.org/0000-0001-7109-3038)
- Felipe M. A. da Silva (ORCID: https://orcid.org/0000-0002-1809-1372)
- Moysés Batista de Araújo Júnior (ORCID: https://orcid.org/0000-0003-3837-1440)
- Célio Fernando Figueiredo Angolini (ORCID: https://orcid.org/0000-0002-2611-3471)
- Héctor H. F. Koolen (ORCID: https://orcid.org/0000-0002-0181-348X)
- Fabiana Elaine Casarin (ORCID: https://orcid.org/0000-0001-5908-7487)
Publication Details
- Journal
- Journal of the Brazilian Chemical Society
- Published
- 2025-01-01
- DOI
- https://doi.org/10.21577/0103-5053.20250146
- Primary Topic
- Aquaculture Nutrition and Growth
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado do Amazonas