Manadomanzamines A and B: a novel alkaloid ring system with potent activity against mycobacteria and HIV-1

J Am Chem Soc. 2003 Nov 5;125(44):13382-6. doi: 10.1021/ja030087z.

Abstract

Two novel alkaloids, named manadomanzamines A (1) and B (2), were isolated from an Indonesian sponge Acanthostrongylophora sp. (Haplosclerida: Petrosiidae). Their structures were elucidated and shown to be a novel organic skeleton related to the manzamine type alkaloids. Their absolute configuration and conformation were determined by CD, NOESY, and molecular modeling analysis. The microbial community analysis for the sponge that produces these unprecedented alkaloids has also been completed. Manadomanzamines A (1) and B (2) exhibited strong activity against Mycobacterium tuberculosis (Mtb) with MIC values of 1.9 and 1.5 mug/mL, respectively. Manadomanzamines A and B also exhibit activities against human immunodeficiency virus (HIV-1) and AIDS opportunistic fungal infections.

Publication types

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

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Cell Line, Tumor
  • Chlorocebus aethiops
  • Drug Screening Assays, Antitumor
  • HIV-1 / drug effects*
  • Humans
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Mycobacterium tuberculosis / drug effects*
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry
  • Vero Cells

Substances

  • Alkaloids
  • Indole Alkaloids
  • manadomanzamine A