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Antifungal polyketides from the Picea rubens and Vaccinium angustifolium endophyte Lachnellula calyciformis

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Abstract

As part of a survey of foliar endophytes of conifers in the Acadian forest, we isolated a strain of Lachnellula calyciformis from a healthy Picea rubens needle. From this fungus, the new natural products deoxylachnellulone (3) and lachnelluloic acid B (5), and the known metabolite lachnellulone (1), were isolated and structurally characterized. Isolachnellulone (2) and isodeoxylachnellulone (4) occurred as isomers resulting from the facile isomerization of lachnellulone (1) and deoxylachnellulone (3), respectively. The natural products lachnellulone (1) and deoxylachnellulone (3) were also confirmed from two strains of L. calyciformis isolated as leaf and stem endophytes of Vaccinium angustifolium in eastern Canada, representing the first record of this species from a non-conifer host. All isolated compounds displayed moderate antifungal and antibiotic activity. This study of biologically active natural products from a conifer endophyte highlights the increasing apparent complexity of their collective life histories.

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Acknowledgments

The authors thank Kim McDonald and Blake Green (Carleton University) for technical assistance with the isolation of natural products, Mark Sumarah (Agriculture and Agri-Food Canada) for providing blueberry Lachnellula isolates, Justin Renaud (Agriculture and Agri-Food Canada) for the acquisition of HRMS data, Jeff Manthorpe (Carleton University) for providing helpful comments on the manuscript, the Microbiology Molecular Technologies Laboratory (MMTL) group of the Ottawa Research and Development Centre (Agriculture and Agri-Food Canada) for processing DNA sequences, and the DAOMC for culture preservation. We also thank S. Clayden and D. McAlpine (New Brunswick Museum) and G. Adams (JD Irving, Ltd) for organizing collecting trips in New Brunswick and Dr. David Malloch for graciously hosting J.B. Tanney.

Funding

This study was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC SYN 479724-15, NSERC CRDPJ 421782-11, PGSD2-459312-2014), Mitacs (IT06326), and JD Irving, Limited.

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Authors and Affiliations

  1. Department of Chemistry, Carleton University, Ottawa, ON, K1S 5B6, Canada

    David R. McMullin, Grace J. Daly & J. David Miller

  2. Pacific Forestry Centre, Natural Resources Canada, Victoria, BC, V8Z 1M5, Canada

    Joey B. Tanney

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  1. David R. McMullin
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  2. Joey B. Tanney
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Correspondence to J. David Miller.

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McMullin, D.R., Tanney, J.B., Daly, G.J. et al. Antifungal polyketides from the Picea rubens and Vaccinium angustifolium endophyte Lachnellula calyciformis. Mycol Progress 19, 1101–1112 (2020). https://doi.org/10.1007/s11557-020-01620-5

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