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

Marcelo R. de Amorim; E. M.Kithsiri Wijeratne; Shengliang Zhou; A. Elizabeth Arnold; Andrea N.L. Batista; João M. Batista; Lourdes C. dos Santos; A. A.Leslie Gunatilaka

doi:10.1016/j.tet.2020.131525

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

Marcelo R. de Amorim, E. M.Kithsiri Wijeratne, Shengliang Zhou, A. Elizabeth Arnold, Andrea N.L. Batista, João M. Batista, Lourdes C. dos Santos, A. A.Leslie Gunatilaka

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English (US)
Article number	131525
Journal	Tetrahedron
Volume	76
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2020.131525
State	Published - Oct 23 2020

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2020.131525

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de Amorim, M. R., Wijeratne, E. M. K., Zhou, S., Arnold, A. E., Batista, A. N. L., Batista, J. M., dos Santos, L. C., & Gunatilaka, A. A. L. (2020). An epigenetic modifier induces production of 3-(4-oxopyrano)-chromen-2-ones in Aspergillus sp. AST0006, an endophytic fungus of Astragalus lentiginosus. Tetrahedron, 76(43), Article 131525. https://doi.org/10.1016/j.tet.2020.131525

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

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",

author = "{de Amorim}, {Marcelo R.} and Wijeratne, {E. M.Kithsiri} and Shengliang Zhou and Arnold, {A. Elizabeth} and Batista, {Andrea N.L.} and Batista, {Jo{\~a}o M.} and {dos Santos}, {Lourdes C.} and Gunatilaka, {A. A.Leslie}",

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year = "2020",

month = oct,

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doi = "10.1016/j.tet.2020.131525",

language = "English (US)",

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AU - Wijeratne, E. M.Kithsiri

AU - Zhou, Shengliang

AU - Arnold, A. Elizabeth

AU - Batista, Andrea N.L.

AU - Batista, João M.

AU - dos Santos, Lourdes C.

AU - Gunatilaka, A. A.Leslie

PY - 2020/10/23

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N2 - 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.

AB - 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.

KW - Aspergillus sp. AST0006

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KW - Epigenetic modifier

KW - Natural products

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

Abstract

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