Peloruside E (22-Norpeloruside A), a Pelorusane Macrolide from the New Zealand Marine Sponge Mycale hentscheli, Retains Microtubule-Stabilizing Properties

J Nat Prod. 2018 Sep 28;81(9):2125-2128. doi: 10.1021/acs.jnatprod.8b00557. Epub 2018 Sep 6.

Abstract

A new peloruside congener, peloruside E (5), has been isolated in sub-milligram quantities from a specimen of the New Zealand marine sponge Mycale hentscheli. The structure of 5 differs from the parent compound peloruside A (1) by replacement of the C-10 gem-dimethyl moiety with a monomethyl substituent and represents the first structural deviation in the pelorusane scaffold. Peloruside E (5) is potently antiproliferative (HL-60, IC50 90 nM, cf. 1, 19 nM) and polymerizes purified tubulin, albeit at a rate lower than that of 1.

MeSH terms

  • Animals
  • HL-60 Cells
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microtubules / drug effects*
  • Porifera / chemistry*
  • Tubulin Modulators / pharmacology*

Substances

  • Macrolides
  • Tubulin Modulators