Scalarane sesterterpenoids: semisynthesis and biological activity

J Nat Prod. 2009 Aug;72(8):1492-6. doi: 10.1021/np900326a.

Haidy N Kamel ¹, Young B Kim, John M Rimoldi, Frank R Fronczek, Daneel Ferreira, Marc Slattery

Affiliations

Affiliation

1 Departments of Pharmacognosy and Medicinal Chemistry, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, Mississippi 38677, USA.

PMID: 19658408 DOI: 10.1021/np900326a

Abstract

Aiming to improve the potency and selectivity of scalarane sesterterpenoids, a series of natural and semisynthetic analogues, derived from the cytotoxic naturally abundant sesterterpene heteronemin (1), were evaluated for their in vitro antimicrobial and cytotoxic properties. The new sesterterpenes 16-O-methylsesterstatin 4 (6c), 17, 24-dihydroheteronemin (7a), 16, 25-deacetoxy-17, 24-dihydroheteronemin (7b), and 16-deacetoxy-25-methoxy-17, 24-dihydroheteronemin (7c) were structurally defined via physical data analyses. Scalarane sesterterpenes possessing an unsaturated 1,4-dialdehyde moiety showed potent inhibitory activity against methicillin-resistant Staphylococcus aureus at concentrations that are not significantly cytotoxic to mammalian cells. The structural features for the cytotoxicity of scalarane sesterterpenoids are discussed.

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