TY - JOUR
T1 - An epigenetic modifier induces production of 3-(4-oxopyrano)-chromen-2-ones in Aspergillus sp. AST0006, an endophytic fungus of Astragalus lentiginosus
AU - de Amorim, Marcelo R.
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
N1 - Funding Information:
This work was supported by the National Institutes of Health grants ( R01 CA90265 and P41 GM094060 ) awarded to A.A.L.G. We thank São Paulo Research Foundation ( FAPESP ) for the scholarship and research grants awarded to M.R.A. [# 2018/05905-5 ] and J.M.B.J. [# 2014/25222-9 ], respectively. We thank Prof. Lijiang Xuan of Center for Modernization of TCM, Shanghai Institute of Materia Medica, P. R. China, for obtaining HRESIMS data. This research was also supported by the College of Agriculture & Life Sciences of the University of Arizona and the Center for Scientific Computing (NCC/GridUNESP) of São Paulo State University ( UNESP ).
Funding Information:
This work was supported by the National Institutes of Health grants (R01 CA90265 and P41 GM094060) awarded to A.A.L.G. We thank S?o Paulo Research Foundation (FAPESP) for the scholarship and research grants awarded to M.R.A. [#2018/05905-5] and J.M.B.J. [#2014/25222-9], respectively. We thank Prof. Lijiang Xuan of Center for Modernization of TCM, Shanghai Institute of Materia Medica, P. R. China, for obtaining HRESIMS data. This research was also supported by the College of Agriculture & Life Sciences of the University of Arizona and the Center for Scientific Computing (NCC/GridUNESP) of Sa?o Paulo State University (UNESP).
Publisher Copyright:
© 2020 Elsevier Ltd
PY - 2020/10/23
Y1 - 2020/10/23
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
KW - Aspyranochromenones A and B
KW - Endophytic fungus
KW - Epigenetic modifier
KW - Natural products
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U2 - 10.1016/j.tet.2020.131525
DO - 10.1016/j.tet.2020.131525
M3 - Article
AN - SCOPUS:85089965266
SN - 0040-4020
VL - 76
JO - Tetrahedron
JF - Tetrahedron
IS - 43
M1 - 131525
ER -