Turonicin A, an antifungal linear polyene polyketide from an Australian Streptomyces sp.

Rachel Chen, Scott A. Minns, John A. Kalaitzis, Mark S. Butler, Maira Rosin, Daniel Vuong, Soo Sum Lean, Yit-Heng Chooi, Ernest Lacey, Andrew M. Piggott*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Turonicin A (1) was isolated from Streptomyces sp. MST-123921, which was recovered from soil collected on the banks of the Turon River in New South Wales, Australia. Turonicin A (1) is an amphoteric linear polyene polyketide featuring independent pentaene and tetraenone chromophores and is structurally related to linearmycins A-C (2-4). The structure of 1 was determined by detailed spectroscopic analysis and comparison to literature data. Bioinformatic analysis of the linearmycin biosynthetic gene cluster also allowed the previously unresolved absolute stereostructures of 2-4 to be elucidated. Turonicin A (1) exhibited very potent activity against the fungi Candida albicans (MIC 0.0031 μg/mL, 2.7 nM) and Saccharomyces cerevisiae (MIC 0.0008 μg/mL, 0.7 nM), moderate activity against the bacteria Bacillus subtilis (MIC 0.097 μg/mL, 85 nM) and Staphylococcus aureus (MIC 0.39 μg/mL, 340 nM), and no cytotoxicity against human fibroblasts, making it an attractive candidate for further development as a potential next-generation antibiotic scaffold.

Original languageEnglish
Pages (from-to)2054-2058
Number of pages5
JournalJournal of Natural Products
Volume86
Issue number8
Early online date1 Aug 2023
DOIs
Publication statusPublished - 25 Aug 2023

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