Halichondria cylindrata

Cylindramide (90) is a cytotoxic compound isolated from Halichondria cylindrata (7.10 s % wet wt.), but very likely of bacterial origin [148]. The structure was deduced from spectroscopic analysis, the relative stereochemistry (only) of the bicyclo[3.3.0]octene unit by NOESY techniques, and the absolute stereochemistry of the amino acid of the tetramic acid ring (25,35) from the recovery of erythtro-L-(3-hydroxyomithine from oxidative degradation of 90. It showed cytotoxicity to B16 melanoma cells (IC50 0.8 (ig/ml). 

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],... 

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]. 

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... 

Kanazawa S, Fusetani N et al (1993) Cylindramide cytotoxic tetramic acid lactam from the marine sponge Halichondria cylindrata Tanita Hoshino. Tetrahedron Lett 34 1065-1068... 

Cylindramide (1) was isolated in 1993 from the marine sponge Halichondria cylindrata by Fusetani and coworkers and showed cytotoxicity against B16 melanoma cells. ... 

Halicylindrosides are P-N-acetylglucosaminylceramides that were isolated from Halichondria cylindrata (Halichondrida, Halichondriidae) harvested on the Japanese coast south of Tokyo. Halicylindrosides Bj-Be differ from halicylindrosides A1-A4 only by the presence of a hydroxyl group at 2 on the fatty chain of the amide part (Li, Matsunaga, and... 

Kanazawa, S., Eusetani, N., and Matsunaga, S. (1993) Cylindramide cytotoxic add lactam from the marine sponge, Halichondria cylindrata. Tetrahedron, 48, 5467-5472. 

Li, H.-Y, Matsunaga, S., and Fusetani, N. (1995a) Halicylindrosides, antifungal and cytotoxic cerebrosides from the marine sponge Halichondria cylindrata. Tetrahedron, 51, 2273-2280. 

---