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Issue 4, 2011
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Reveromycins Revealed: New polyketide spiroketals from Australian marine-derived and terrestrial Streptomyces spp. A case of natural productsvs. artifacts

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Abstract

Chemical analysis of fermentation products from two Australian Streptomyces isolates yielded all four known and twelve new examples of the rare reveromycin class of polyketide spiroketals, including hemi-succinates, hemi-fumarates and hemi-furanoates. Reveromycins were identified with the aid of HPLC-DAD-MS and HPLC-DAD-SPE-NMR methodology, and structures were assigned by detailed spectroscopic analysis. The structural and mechanistic requirements for an unprecedented hemi-succinate : ketal-succinyl equilibrium were defined and provided a basis for proposing that reveromycin 4′-methyl esters and 5,6-spiroketals were artifacts. A plausible reveromycin polyketide biosynthesis is proposed, requiring a 2-methylsuccinyl-CoA starter unit, with flexible incorporation of a C6–8polyketide chain extension and diacid esterification units. Structure activity relationship investigations by co-metabolites were used to assess the anticancer, antibacterial and antifungal properties of reveromycins.

Graphical abstract: Reveromycins Revealed: New polyketide spiroketals from Australian marine-derived and terrestrial Streptomyces spp. A case of natural productsvs. artifacts

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Publication details

The article was received on 01 Sep 2010, accepted on 29 Oct 2010 and first published on 14 Dec 2010


Article type: Paper
DOI: 10.1039/C0OB00654H
Citation: Org. Biomol. Chem., 2011,9, 1201-1211
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    Reveromycins Revealed: New polyketide spiroketals from Australian marine-derived and terrestrial Streptomyces spp. A case of natural productsvs. artifacts

    L. Fremlin, M. Farrugia, A. M. Piggott, Z. Khalil, E. Lacey and R. J. Capon, Org. Biomol. Chem., 2011, 9, 1201
    DOI: 10.1039/C0OB00654H

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