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

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Lacey, A. E., Minns, S. A., Chen, R., Vuong, D., Lacey, E., Kalaitzis, J. A., Tan, Y. P., Shivas, R. G., Butler, M. S. and Piggott, A. M. (2024) Talcarpones A and B: bisnaphthazarin-derived metabolites from the Australian fungus Talaromyces johnpittii sp. nov. MST-FP2594. The Journal of Antibiotics, 77 . pp. 147-155. ISSN 1881-1469

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Article Link: https://doi.org/10.1038/s41429-023-00688-x


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.

Item Type:Article
Corporate Creators:Department of Agriculture and Fisheries, Queensland
Business groups:Biosecurity Queensland
Keywords:Fungi ; Natural products ; Structure elucidation
Subjects:Science > Biology > Biochemistry
Science > Biology > Molecular Biology
Agriculture > Agriculture (General) > Agricultural chemistry. Agricultural chemicals
Plant culture
Plant culture > Economic botany
Live Archive:05 Mar 2024 23:46
Last Modified:05 Mar 2024 23:46

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