TY - JOUR
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.
N1 - Funding Information:
This project was funded by Grant R01 CA090265 of the National Cancer Institute (NCI) and Grant P41 GM094060 of the National Institute of General Medical Sciences (NIGMS). We thank the National Science Foundation for supporting the work in which the strain was isolated initially (DEB-0640996 to A.E.A.) and China Scholarship Council for awarding a visiting scholar fellowship (to W.Q.).
Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy
PY - 2021/9/24
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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U2 - 10.1021/acs.jnatprod.1c00662
DO - 10.1021/acs.jnatprod.1c00662
M3 - Review article
C2 - 34495663
AN - SCOPUS:85115637435
VL - 84
SP - 2575
EP - 2586
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 9
ER -