2008
DOI: 10.1021/np800230d
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Revisiting the Sponge Sources, Stereostructure, and Biological Activity of Cyclocinamide A

Abstract: The dramatic biogeographical variations in the secondary metabolites from Psammocinia aff. bulbosa have complicated our efforts to re-isolate the two most cytotoxic of its metabolites, (+)-psymberin and (+)-cyclocinamide A. Reported now are the results of a new study that demonstrates our ability to repeatedly isolate these two compounds through targeted collection efforts. Additional study of the new sample of (+)-cyclocinamide A has enabled finalizing its biological activity and absolute stereochemistry as 4… Show more

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Cited by 19 publications
(10 citation statements)
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“…The compound's relative conguration was also determined, 726,727 while the relative conguration of the C-36 to C-42 portion of hemicalide 1107 was also solved by synthesis. 728,729 Total syntheses of polyketides gracilioether B and C 730,731 and hippolachnin, 732,733 mycothiazole, [734][735][736] aromatic renieramycin I, 737,738 and peptides cyclocinamide A, 739 corticiamide B, [740][741][742] stylissamide X 743,744 and stylissatin A 745,746 have all been realised. The total synthesis of yaku'amide A 1108, including eight possible stereoisomers of its core region, required revision of structure, and also that of congener B 1109.…”
Section: Spongesmentioning
confidence: 99%
“…The compound's relative conguration was also determined, 726,727 while the relative conguration of the C-36 to C-42 portion of hemicalide 1107 was also solved by synthesis. 728,729 Total syntheses of polyketides gracilioether B and C 730,731 and hippolachnin, 732,733 mycothiazole, [734][735][736] aromatic renieramycin I, 737,738 and peptides cyclocinamide A, 739 corticiamide B, [740][741][742] stylissamide X 743,744 and stylissatin A 745,746 have all been realised. The total synthesis of yaku'amide A 1108, including eight possible stereoisomers of its core region, required revision of structure, and also that of congener B 1109.…”
Section: Spongesmentioning
confidence: 99%
“…573 The accepted structure of cyclocinamide A (Psammocinia sp. ), originally reported in 1997 and revised in 2008, 574,575 has been disproven by synthesis leaving the structure of the natural product as a mystery. 576 Namalide 620 is a potent carboxypeptidase A inhibitor isolated from Siliquariaspongia mirabilis (Nama Is., Chuuk Lagoon, Federated States of Micronesia).…”
Section: Spongesmentioning
confidence: 99%
“…Obtaining and examining biogeographical-based collections of sponges whose extracts have exhibited solid tumor selectivity in the in vitro cytotoxicity disk diffusion assay can be quite rewarding 93,94. Applying this approach facilitated gaining a comprehensive understanding of the variations in the constituents of Cacospongia mycofijiensis .…”
Section: Sponges – Current Milestone Discoveriesmentioning
confidence: 99%