Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir

Wei Qu; E. M. Kithsiri Wijeratne; Bharat P. Bashyal; Jian Xu; Ya Ming Xu; Manping X. Liu; Marielle C. Inácio; A. Elizabeth Arnold; Jana M. U’Ren; A. A. Leslie Gunatilaka

doi:10.1021/acs.jnatprod.1c00662

Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir

Wei Qu, E. M. Kithsiri Wijeratne, Bharat P. Bashyal, Jian Xu, Ya Ming Xu, Manping X. Liu, Marielle C. Inácio, A. Elizabeth Arnold, Jana M. U’Ren, A. A. Leslie Gunatilaka

Research output: Contribution to journal › Review article › peer-review

4 Scopus citations

Abstract

Six new 6-isopentylsphaeropsidones, strobiloscyphones A-F ( 1 - 6 ), and a new hexadecanoic acid, (2Z,4E,6E)-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic acid ( 7 ), together with sphaeropsidone ( 8 ) and its known synthetic analogue 5-dehydrosphaeropsidone ( 9 ) were isolated fromStrobiloscyphasp. AZ0266, a fungus inhabiting the leaf litter of Douglas fir (Pseudotsuga menziesii). The structures of 1 - 7 were established on the basis of their high-resolution mass and 1D and 2D NMR spectroscopic data, and their relative and/or absolute configurations were determined by NOE, comparison of experimental and calculated ECD spectra, and application of the modified Mosher’s ester method. Of these, strobiloscyphone F ( 6 ) contains a novel highly oxygenated tetracyclic oxireno-octahydrodibenzofuran ring system. Natural products 1 , 6 , and 9 and the semisynthetic analogue 12 derived from 8 exhibited cytotoxic activity, whereas 9 and 12 showed antimicrobial activity. Possible biosynthetic pathways to 1 - 6 , 8 , and 9 are proposed.

Original language	English (US)
Pages (from-to)	2575-2586
Number of pages	12
Journal	Journal Of Natural Products
Volume	84
Issue number	9
DOIs	https://doi.org/10.1021/acs.jnatprod.1c00662
State	Published - Sep 24 2021

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.1c00662

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Qu, W., Kithsiri Wijeratne, E. M., Bashyal, B. P., Xu, J., Xu, Y. M., Liu, M. X., Inácio, M. C., Arnold, A. E., U’Ren, J. M., & Leslie Gunatilaka, A. A. (2021). Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir. Journal Of Natural Products, 84(9), 2575-2586. https://doi.org/10.1021/acs.jnatprod.1c00662

Qu, W, Kithsiri Wijeratne, EM, Bashyal, BP, Xu, J, Xu, YM, Liu, MX, Inácio, MC, Arnold, AE , U’Ren, JM & Leslie Gunatilaka, AA 2021, 'Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir', Journal Of Natural Products, vol. 84, no. 9, pp. 2575-2586. https://doi.org/10.1021/acs.jnatprod.1c00662

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title = "Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir",

abstract = "Six new 6-isopentylsphaeropsidones, strobiloscyphones A-F ( 1 - 6 ), and a new hexadecanoic acid, (2Z,4E,6E)-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic acid ( 7 ), together with sphaeropsidone ( 8 ) and its known synthetic analogue 5-dehydrosphaeropsidone ( 9 ) were isolated fromStrobiloscyphasp. AZ0266, a fungus inhabiting the leaf litter of Douglas fir (Pseudotsuga menziesii). The structures of 1 - 7 were established on the basis of their high-resolution mass and 1D and 2D NMR spectroscopic data, and their relative and/or absolute configurations were determined by NOE, comparison of experimental and calculated ECD spectra, and application of the modified Mosher{\textquoteright}s ester method. Of these, strobiloscyphone F ( 6 ) contains a novel highly oxygenated tetracyclic oxireno-octahydrodibenzofuran ring system. Natural products 1 , 6 , and 9 and the semisynthetic analogue 12 derived from 8 exhibited cytotoxic activity, whereas 9 and 12 showed antimicrobial activity. Possible biosynthetic pathways to 1 - 6 , 8 , and 9 are proposed.",

author = "Wei Qu and {Kithsiri Wijeratne}, {E. M.} and Bashyal, {Bharat P.} and Jian Xu and Xu, {Ya Ming} and Liu, {Manping X.} and In{\'a}cio, {Marielle C.} and Arnold, {A. Elizabeth} and U{\textquoteright}Ren, {Jana M.} and {Leslie Gunatilaka}, {A. A.}",

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year = "2021",

month = sep,

day = "24",

doi = "10.1021/acs.jnatprod.1c00662",

language = "English (US)",

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T1 - Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir

AU - Qu, Wei

AU - Kithsiri Wijeratne, E. M.

AU - Bashyal, Bharat P.

AU - Xu, Jian

AU - Xu, Ya Ming

AU - Liu, Manping X.

AU - Inácio, Marielle C.

AU - Arnold, A. Elizabeth

AU - U’Ren, Jana M.

AU - Leslie Gunatilaka, A. A.

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Y1 - 2021/9/24

N2 - Six new 6-isopentylsphaeropsidones, strobiloscyphones A-F ( 1 - 6 ), and a new hexadecanoic acid, (2Z,4E,6E)-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic acid ( 7 ), together with sphaeropsidone ( 8 ) and its known synthetic analogue 5-dehydrosphaeropsidone ( 9 ) were isolated fromStrobiloscyphasp. AZ0266, a fungus inhabiting the leaf litter of Douglas fir (Pseudotsuga menziesii). The structures of 1 - 7 were established on the basis of their high-resolution mass and 1D and 2D NMR spectroscopic data, and their relative and/or absolute configurations were determined by NOE, comparison of experimental and calculated ECD spectra, and application of the modified Mosher’s ester method. Of these, strobiloscyphone F ( 6 ) contains a novel highly oxygenated tetracyclic oxireno-octahydrodibenzofuran ring system. Natural products 1 , 6 , and 9 and the semisynthetic analogue 12 derived from 8 exhibited cytotoxic activity, whereas 9 and 12 showed antimicrobial activity. Possible biosynthetic pathways to 1 - 6 , 8 , and 9 are proposed.

AB - Six new 6-isopentylsphaeropsidones, strobiloscyphones A-F ( 1 - 6 ), and a new hexadecanoic acid, (2Z,4E,6E)-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic acid ( 7 ), together with sphaeropsidone ( 8 ) and its known synthetic analogue 5-dehydrosphaeropsidone ( 9 ) were isolated fromStrobiloscyphasp. AZ0266, a fungus inhabiting the leaf litter of Douglas fir (Pseudotsuga menziesii). The structures of 1 - 7 were established on the basis of their high-resolution mass and 1D and 2D NMR spectroscopic data, and their relative and/or absolute configurations were determined by NOE, comparison of experimental and calculated ECD spectra, and application of the modified Mosher’s ester method. Of these, strobiloscyphone F ( 6 ) contains a novel highly oxygenated tetracyclic oxireno-octahydrodibenzofuran ring system. Natural products 1 , 6 , and 9 and the semisynthetic analogue 12 derived from 8 exhibited cytotoxic activity, whereas 9 and 12 showed antimicrobial activity. Possible biosynthetic pathways to 1 - 6 , 8 , and 9 are proposed.

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Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscyphasp. AZ0266, a Leaf-Associated Fungus of Douglas Fir

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