Crambescidin 826 and dehydrocrambine A: new polycyclic guanidine alkaloids from the marine sponge Monanchora sp. that inhibit HIV-1 fusion

J Nat Prod. 2003 Nov;66(11):1490-4. doi: 10.1021/np030256t.

Abstract

Two new polycyclic guanidine alkaloids, crambescidin 826 (1) and dehydrocrambine A (2), and the known compounds crambescidin 800 (3) and fromiamycalin (4) were isolated from the marine sponge Monanchora sp. The structures of 1 and 2 were elucidated by 2D NMR and mass spectrometry, and relative stereochemistry was established by analysis of coupling constants and ROESY spectra. The pentacyclic guanidine alkaloids 1, 3, and 4 inhibit HIV-1 envelope-mediated fusion in vitro with IC(50)'s of 1-3 microM, while compound 2, a tricyclic guanidine alkaloid, showed weaker inhibition, with an IC(50) of approximately 35 microM.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Animals
  • Anti-HIV Agents* / chemistry
  • Anti-HIV Agents* / isolation & purification
  • Anti-HIV Agents* / pharmacology
  • Guanidines* / chemistry
  • Guanidines* / isolation & purification
  • Guanidines* / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Palau
  • Porifera / chemistry*
  • Spiro Compounds* / chemistry
  • Spiro Compounds* / isolation & purification
  • Spiro Compounds* / pharmacology

Substances

  • Alkaloids
  • Anti-HIV Agents
  • Guanidines
  • Spiro Compounds
  • crambescidin 826
  • dehydrocrambine A