Production of Oosporein and Related Bibenzoquinone Analogues in Arcopilus amazonicus Revealed by Genome Mining and Mass Spectrometry Analysis

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Abstract
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.