Makaluvic acids from the South African latrunculid sponge Strongylodesma aliwaliensis

Robert A Keyzers; Catherine E Arendse; Denver T Hendricks; Toufiek Samaai; Michael T Davies-Coleman

doi:10.1021/np049589w

Makaluvic acids from the South African latrunculid sponge Strongylodesma aliwaliensis

J Nat Prod. 2005 Apr;68(4):506-10. doi: 10.1021/np049589w.

Authors

Robert A Keyzers¹, Catherine E Arendse, Denver T Hendricks, Toufiek Samaai, Michael T Davies-Coleman

Affiliation

¹ Department of Chemistry, Rhodes University, Grahamstown, South Africa, Division of Medical Biochemistry, University of Cape Town, Rondebosch, South Africa.

PMID: 15844938
DOI: 10.1021/np049589w

Abstract

Two new metabolites, makaluvic acid C (1) and N-1-beta-d-ribofuranosylmakaluvic acid C (2), were isolated from the recently described sponge Strongylodesma aliwaliensis collected off the east coast of South Africa. Standard spectroscopic techniques provided the structures of both compounds. Chiral GC analysis of the peracetylated aldononitrile derivative of the acid hydrolysate of 2 confirmed the d-configuration of the ribose moiety in this compound. Compound 2 and four related pyrroloquinoline metabolites, isolated previously from S. aliwaliensis, exhibited in vitro cytotoxicity against esophageal cancer cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Alkaloids / pharmacology
Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Antineoplastic Agents / pharmacology
Drug Screening Assays, Antitumor
Inhibitory Concentration 50
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Porifera / chemistry*
Pyrroles / chemistry
Pyrroles / isolation & purification*
Pyrroles / pharmacology
South Africa
Tumor Cells, Cultured

Substances

Alkaloids
Antineoplastic Agents
N-1-beta-D-ribofuranosylmakaluvic acid C
Pyrroles
makaluvic acid C