Modulation of polyketide biosynthetic pathway of the endophytic fungus, Anteaglonium sp. FL0768, by copper (II) and anacardic acid. (December 2018)

• Record Type: Journal Article
• Authors: Mafezoli, Jair; Xu, Ya-ming; Hilário, Felipe; Freidhof, Brandon; Espinosa-Artiles, Patricia; dos Santos, Lourdes C.; de Oliveira, Maria C.F.; Gunatilaka, A.A. Leslie
• Is Part Of: Phytochemistry letters. Volume 28(2018)
• Page Start: 157
• Page End: 163
• Publication Date: 2018-12
• Subjects: Anteaglonium -- Endophytic fungus -- Copper (II) -- Anacardic acid -- Polyketide biosynthesis; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2018.10.011
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Secondary metabolite profile of the endophytic fungus, Anteaglonium sp. FL0768, was found to be affected by culture conditions. Incorporation of Cu 2+ enhanced production of metabolites and drastically affected the polyketide biosynthetic pathway. The histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile. The epigenetic modifiers, 5-azacytidine and suberoyl anilide hydroxamic acid had no effect on its secondary metabolite profile. Abstract: In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1 ), herbarin (2 ), 1-hydroxydehydroherbarin (3 ), scorpinone (4 ), and the methylated hexaketide 9 S, 11 R -(+)-ascosalitoxin (5 ). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4 ) as the major metabolite together with 1-hydroxydehydroherbarin (3 ) and a different methylated hexaketide, ascochitine (6 ). Intriguingly, incorporaion of Cu 2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE4 (7 ), palmarumycin CP4 (8 ), and palmarumycin CP1 (9 ), in addition to ascochitine (6 ). The structure of the new metabolite7 was established with the help of spectroscopic data and by MnO2 oxidation to the known pentaketide dimer, palmarumycin CP3 (10 ). Biosynthetic pathways to some metabolites in Anteaglonium sp. FL0768 are presented and possible effects of AA and Cu 2+ on these pathways are discussed.