2. Academic Validation
  3. An epigenetic modifier induces production of 3-(4-oxopyrano)-chromen-2-ones in Aspergillus sp. AST0006, an endophytic fungus of Astragalus lentiginosus

An epigenetic modifier induces production of 3-(4-oxopyrano)-chromen-2-ones in Aspergillus sp. AST0006, an endophytic fungus of Astragalus lentiginosus

  • Tetrahedron. 2020 Oct 23;76(43):131525. doi: 10.1016/j.tet.2020.131525.
Marcelo R de Amorim 1 2,  E M Kithsiri Wijeratne 1,  Shengliang Zhou 1 3,  A Elizabeth Arnold 4,  Andrea N L Batista 5,  João M Batista Jr 6,  Lourdes C Dos Santos 2,  A A Leslie Gunatilaka 1
Affiliations

Affiliations

  • 1 Southwest Center for Natural Products Research, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706, United States.
  • 2 Institute of Chemistry, São Paulo State University, Araraquara, São Paulo 14800-900, Brazil.
  • 3 The Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, 101 Shanghai Rd, Xuzhou 221116, P. R. China.
  • 4 School of Plant Sciences, College of Agriculture and Life Sciences, University of Arizona, Tucson, Arizona 85721, United States.
  • 5 Department of Organic Chemistry, Chemistry Institute, Fluminense Federal University, Niterói, RJ 24020-141, Brazil.
  • 6 Institute of Science and Technology, Federal University of São Paulo, São José dos Campos, São Paulo 12231-280, Brazil.
PMID: 33716326 DOI: 10.1016/j.tet.2020.131525
Abstract

Incorporation of the epigenetic modifier suberoylanilide hydroxamic acid (SAHA) into a potato dextrose broth culture of the endophytic fungus Aspergillus sp. AST0006 affected its polyketide biosynthetic pathway providing two new 3-(4-oxopyrano)-chromen-2-ones, aspyranochromenones A (1) and B (2), and the isocoumarin, (-)-6,7-dihydroxymellein (3). Eight additional metabolites (4-11) and two biotransformation products of SAHA (12-13) were also encountered. The planar structures and relative configurations of the new metabolites 1-2 were elucidated with the help of high-resolution mass, 1D and 2D NMR spectroscopic data and the absolute configurations of 1-3 were determined by comparison of experimental and calculated ECD data. Possible biosynthetic pathways to 1 and 2 are presented.

Keywords

Aspergillus sp. AST0006; Aspyranochromenones A and B; Endophytic fungus; Epigenetic modifier; Natural products.

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