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

Author(s)

de Amorim, Marcelo R. ^{[1, 2]} ; Wijeratne, E. M. Kithsiri ^[2] ; Zhou, Shengliang ^{[2, 3]} ; Arnold, A. Elizabeth ^[4] ; Batista, Andrea N. L. ^[5] ; Batista, Joao M. ^[6] ; dos Santos, Lourdes C. ^[1] ; Gunatilaka, A. A. Leslie ^[2]

Affiliation

^[1] Sao Paulo State Univ, Inst Chem, BR-14800900 Araraquara, SP - Brazil

^[2] Univ Arizona, Coll Agr & Life Sci, Southwest Ctr Nat Prod Res, Sch Nat Resources & Environm, 250 E Valencia Rd, Tucson, AZ 85706 - USA

^[3] Jiangsu Normal Univ, Key Lab Biotechnol Med Plants Jiangsu Prov, 101 Shanghai Rd, Xuzhou 221116, Jiangsu - Peoples R China

^[4] Univ Arizona, Coll Agr & Life Sci, Sch Plant Sci, Tucson, AZ 85721 - USA

^[5] Fluminense Fed Univ, Chem Inst, Dept Organ Chem, BR-24020141 Niteroi, RJ - Brazil

^[6] Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron; v. 76, n. 43 OCT 23 2020.
• Web of Science Citations: 0

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. (C) 2020 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 18/05905-5 - Epigenetic modifiers: extending the metabolic diversity of endophytic fungi
• Grantee: Marcelo Rodrigues de Amorim
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
• Grantee: João Marcos Batista Junior
• Support Opportunities: Research Grants - Young Investigators Grants