Makaluvic acids from the South African latrunculid sponge Strongylodesma aliwaliensis.
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.
Keyzers
Robert A
RA
Department of Chemistry, Rhodes University, Grahamstown, South Africa, Division of Medical Biochemistry, University of Cape Town, Rondebosch, South Africa.
Arendse
Catherine E
CE
Hendricks
Denver T
DT
Samaai
Toufiek
T
Davies-Coleman
Michael T
MT
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013019:South Africa; D014407:Tumor Cells, Cultured
D000470:Alkaloids; D000970:Antineoplastic Agents; C501023:N-1-beta-D-ribofuranosylmakaluvic acid C; D011758:Pyrroles; C501022:makaluvic acid C