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Talcarpones A and B: bisnaphthazarin-derived metabolites from the Australian fungus Talaromyces johnpittii sp. nov. MST-FP2594

The Journal of Antibiotics volume 77, pages 147–155 (2024)Cite this article

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Abstract

Talcarpones A (1) and B (2) are rare bisnaphthazarin derivatives produced by Talaromyces johnpittii (ex-type strain MST-FP2594), a newly discovered Australian fungus, which is formally described and named herein. The talcarpones were isolated along with the previously reported monomeric naphthoquinone, aureoquinone (3), suggesting a biosynthetic link between these metabolites. Talcarpone A is a lower homologue of hybocarpone (4), which was first isolated from a mycobiont of the lichen Lecanora hybocarpa. The structures of 1 and 2 were elucidated by detailed spectroscopic analysis, molecular modelling and comparison with literature data. Talcarpones 1 and 2 exhibited moderate antifungal activity (MIC 0.78–3.1 µg ml−1) and weak activity against Gram-positive bacteria (MIC 13–25 µg ml−1). The talcarpones also demonstrated noteworthy chemical reactivities, with 2 converting rapidly to 1, which in turn converted slowly to the highly coloured 3. These post-biosynthetic reactions point to a potential ecological role for the talcarpones in providing ongoing (slow-release) physicochemical protection for T. johnpittii against solar irradiation.

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Acknowledgements

Our sincerest gratitude to our friend and colleague Dr John I. Pitt (1937–2022) one of Australia’s greatest mycologists who wrote the books on food mycology that trained the world. Talaromyces johnpittii was collected by John, who recognised the strain’s novelty as a species of value to science. We thank Prof. Alison Rodger (MQ) for assistance with the acquisition of spectroscopic data. Molecular modelling was undertaken with the assistance of resources and services from the National Computational Infrastructure (NCI), supported by the Australian Government. This research was funded, in part, by the Australian Cooperative Research Centres Projects scheme (CRCPFIVE000119).

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Authors and Affiliations

  1. Microbial Screening Technologies, Smithfield, NSW, 2164, Australia

    Alastair E. Lacey, Scott A. Minns, Rachel Chen, Daniel Vuong & Ernest Lacey

  2. School of Natural Sciences, Macquarie University, Macquarie Park, NSW, 2109, Australia

    Ernest Lacey, John A. Kalaitzis & Andrew M. Piggott

  3. Queensland Plant Pathology Herbarium, Department of Agriculture and Fisheries, Brisbane, QLD, 4102, Australia

    Yu Pei Tan & Roger G. Shivas

  4. Centre for Crop Health, University of Southern Queensland, Toowoomba, QLD, 4350, Australia

    Yu Pei Tan & Roger G. Shivas

  5. MSBChem Consulting, New Farm, QLD, 4005, Australia

    Mark S. Butler

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Lacey, A.E., Minns, S.A., Chen, R. et al. Talcarpones A and B: bisnaphthazarin-derived metabolites from the Australian fungus Talaromyces johnpittii sp. nov. MST-FP2594. J Antibiot 77, 147–155 (2024). https://doi.org/10.1038/s41429-023-00688-x

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