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

Leith Fremlin, Michelle Farrugia, Andrew M. Piggott, Zeinab Khalil, Ernest Lacey and Robert J. Capon

Organic Biomolecular Chemistry Chem. 2011, 9, 1201-11.

Publication Date: October 29, 2010


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.

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