2. Academic Validation
  3. Strobiloscyphones A-F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscypha sp. AZ0266, a Leaf-Associated Fungus of Douglas Fir

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

  • J Nat Prod. 2021 Sep 24;84(9):2575-2586. doi: 10.1021/acs.jnatprod.1c00662.
Wei Qu 1 2,  E M Kithsiri Wijeratne 1,  Bharat P Bashyal 1,  Jian Xu 2,  Ya-Ming Xu 1,  Manping X Liu 1,  Marielle C Inácio 1,  A Elizabeth Arnold 3,  Jana M U'Ren 4,  A A Leslie Gunatilaka 1
Affiliations

Affiliations

  • 1 Southwest Center for Natural Products Research, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706, United States.
  • 2 Department of Natural Medicinal Chemistry, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, People's Republic of China.
  • 3 School of Plant Sciences, College of Agriculture and Life Sciences, University of Arizona, Tucson, Arizona 85721, United States.
  • 4 Biosystems Engineering, College of Agriculture and Life Sciences, University of Arizona, Tucson, Arizona 85721, United States.
PMID: 34495663 DOI: 10.1021/acs.jnatprod.1c00662
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 from Strobiloscypha sp. 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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