Turonicin A, an Antifungal Linear Polyene Polyketide from an Australian Streptomyces sp

  • J Nat Prod. 2023 Aug 25;86(8):2054-2058. doi: 10.1021/acs.jnatprod.3c00144.
Rachel Chen  1 ,  Scott A Minns  1 ,  John A Kalaitzis  2 ,  Mark S Butler  3 ,  Maira Rosin  4 ,  Daniel Vuong  2 ,  Soo Sum Lean  5 ,  Yit-Heng Chooi  5 ,  Ernest Lacey  1  2 ,  Andrew M Piggott  2
Affiliations
  • 1. Microbial Screening Technologies Pty. Ltd., Smithfield, NSW 2164, Australia.
  • 2. School of Natural Sciences, Macquarie University, Sydney, NSW 2109, Australia.
  • 3. MSBChem Consulting, New Farm, QLD 4005, Australia.
  • 4. Department of Molecular and Applied Microbiology, Jena Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute, Jena D-07745, Germany.
  • 5. School of Molecular Sciences, The University of Western Australia, Perth, WA 6009, Australia.
PMID: 37526586 DOI: 10.1021/acs.jnatprod.3c00144
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.

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