Zamamidines A and B, new manzamine alkaloids from the sponge Amphimedon species

Org Lett. 2009 Jan 1;11(1):21-4. doi: 10.1021/ol802251q.

Abstract

New manzamine alkaloids, zamamidines A (1) and B (2), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistry of 1 and 2 were elucidated from the spectroscopic data and conformational analysis. Zamamidines A (1) and B (2) are the first manzamine alkaloids possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine H and 1,2,3,4-tetrahydromanzamine B, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Animals
  • Carbazoles / chemistry*
  • Carbazoles / isolation & purification
  • Crystallography, X-Ray
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Porifera / chemistry*
  • Species Specificity
  • Stereoisomerism

Substances

  • Alkaloids
  • Carbazoles
  • Heterocyclic Compounds, 4 or More Rings
  • zamamidine A
  • zamamidine B