Halicylindramides

Halicylindramides - antifungal peptides Polydiscamide A - cytotoxic peptides... 

Halicylindramides A-C (427-429) are antifungal and cytotoxic depsipeptides from Halichondria cylindrata from Japan [358]. Two additional peptides, halicylindramides D (430) and E (431) of which the former is antifungal and cytotoxic, were also isolated from a Japanese collection of H. cylindrata [359],... 

Hyrlios sp. [310,311], and the antifungal peptides halicylindramides from Halicondria sp. [312],... 

Marine natural products bearing a sulfonic acid/sulfonate group are very abundant, with a huge diverse array of structures known. In most cases, this functionality is present in the discodermin-halicylindramide depsipeptides, in sulfonolipids, as well as in assorted metabolites. 

Polydiscamide A (309), discodermins A-H (298-305) and halicylindramides A-E (306-308, 310 and 311) form a series of depsipeptides composed of 13 or 14 amino acids and bear a sulfonic acid group in a cysteic acid residue, with Cys(03H), with the JV-terminus blocked by a formyl group. Their total structures, including absolute stereochemistries, were determined in most cases by a combination of spectral and chemical methods. 

The tridecapeptide polydiscamide A (309) was obtained from an unidentified Caribbean species of Discodermia [220], while discodermins A-H (298-305) were isolated from D. kiiensis. The structures deduced previously for discodermins A-E [221, 222] were later revised on the basis of NMR data and protein sequence analysis [223]. A number of closely related compounds, the tetradecapeptides halicylindramides A-C (306-308) [224], the tridecapeptide halicylindramide D (310) [225], and the truncated linear peptide halicylindramide E [225] (311) were obtained from the sponge Halichondria cylindrata. A microbial origin for these compounds was suggested [226]. 

Perthamide B (1099) is a novel cyclic octapeptide found in a Theonella sp. sponge near Perth, Australia (1122). A collection of the Japanese sponge Halichon-dria cylindrata has afforded halicylindramides A-E (1100-1103), and the absolute configurations are shown (1123,1124). Each compound features a 4-bromophenyl-alanine residue. 

Li H, Matsunaga S, Fusetani N (1995) Halicylindramides A-C, Antifungal and Cytotoxic Depsipeptides from the Marine Sponge Halichondria cylindrata. J Med Chem 38 338... 

Depsipeptide Marine sponge, Halichondria cylindraia Halicylindramides A-C [57]... 

Li, H.-Y, Matsunaga, S., and Fusetani, N. (1995b) Halicylindramides A-C, antifungal and cytotoxic depsipeptides from the marine sponge Halichondria cylindrata. J. Med. Chem., 38, 338-343. 

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