Cytotoxic Pyrroloiminoquinones from Four New Species of South African Latrunculid Sponges†Click to copy article linkArticle link copied!
- Edith M. Antunes
- Denzil R. Beukes
- Michelle Kelly
- Toufiek Samaai
- Louis R. Barrows
- Kathryn M. Marshall
- Catherine Sincich
- Michael T. Davies-Coleman
Abstract
An examination of organic extracts of four new species of South African latrunculid sponges, Tsitsikammapedunculata, T. favus, Latrunculia bellae, and Strongylodesma algoaensis, yielded 13 known and eight new pyrroloiminoquinone alkaloids, 3-dihydro-7,8-dehydrodiscorhabdin C (4), 14-bromo-3-dihydro-7,8-dehydrodiscorhabdin C (5), discorhabdin V (6), 14-bromo-1-hydroxydiscorhabdin V (7), tsitsikammamine A N-18 oxime (10), tsitsikammamine B N-18 oxime (11), 1-methoxydiscorhabdin D (12), and 1-aminodiscorhabdin D (13). Standard spectroscopic methods provided the structures of the pyrroloiminoquinone metabolites, while chiral GC−MS analysis of the acylated ozonolysis products of 21 confirmed the stereochemistry of the l-histidine residue in this compound. The anticancer activity of 20 pyrroloiminoquinone compounds was explored in the HCT-116 cancer cell line screen, and the DNA intercalation of the tsitsikammamines, together with their ability to cleave DNA through topoisomerase I inhibition, is discussed.
†
Dedicated to the late Dr. D. John Faulkner (Scripps) and the late Dr. Paul J. Scheuer (Hawaii) for their pioneering work on bioactive marine natural products.
‡
Department of Chemistry, Rhodes University.
§
Faculty of Pharmacy, Rhodes University.
⊥
National Centre for Aquatic Biodiversity & Biosecurity.
‖
University of Durban Westville.
∇
University of Utah.
°
Scripps Institution of Oceanography.
*
To whom correspondence should be addressed. Tel: +27 46 603 8264. Fax: +27 46 6225109. E-mail: [email protected].
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