Pregnane-10,2-carbolactones from a Hawaiian Marine Sponge in the Genus Myrmekioderma

J Nat Prod. 2016 May 27;79(5):1464-7. doi: 10.1021/acs.jnatprod.6b00042. Epub 2016 Apr 22.

Abstract

Four new pregnanes, 3β,4β-dihydroxy-17-methyl-17α-pregna-5,13-diene-10,2-carbolactone (1), 6β-chloro-3β-hydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (2), 3β-hydroxy-6β-methoxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (3), and 3β,6β-dihydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (4), were isolated from an undescribed species of Myrmekioderma Ehlers along with the known pregnane carbolactone (5). The structures of the new compounds were determined by spectroscopic methods and comparison with previously described compounds. Compound 5 showed almost 4-fold activation of pregnane X receptor, while 2 inhibited BACE1 with an IC50 value of 82 μM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Hawaii
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Porifera / genetics
  • Pregnanes / chemistry
  • Pregnanes / isolation & purification*
  • Pregnanes / pharmacology

Substances

  • Lactones
  • Pregnanes