Macrolide glycoside

The macrolide glycosides, aurisides A (17) and B (18), from the Japanese sea hare Dolabella auricularia show cytotoxicity against HeLa S3 cells with IC50 values of 0.17 and 1.2 pg/ml, respectively [35]. 

Sone H, Kigoshi H, Yamada K (1996) Aurisides A and B. Cytotoxic Macrolide Glycosides from the Japanese Sea Hare Dolabella auricularia. J Org Chem 61 8956... 

Pathirana, C., Tapiolas, D.M., Jensen, P.R., Dwight, R., and Fenical, W., Structure determination of maduralide a new 24-membered ring macrolide glycoside produced by a marine bacterium (Actino-... 

Structural similarity to the sponge-derived 14-membered macrolide glycoside, callipeltoside A (see Section II.C.7). From the same organism, laingolide (18), possessing a 15-membered lactone-lactam structure, was obtained and its planar structure was reported [39]. No bioactivity was described for compounds 17 and 18. 

Sone, H., Kigoshi, H., and Yamada, K. (1996). Aurisides A and B, cytotoxic macrolide glycosides from the Japanese sea hare Dolabella auricularia. J. Org. Chem. 61, 8956-8960. 

The intriguing proposition has been made that the macrolide glycosides as well as lincomycin are "recognized by ribosomal receptor-sites as resembling the terminal unit of peptidyl- or aminoacyl-tRNA.1 ... 

Lyngbyaloside B, a Marine Macrolide Glycoside Total Synthesis and Stereochemical Revision... 

FIG. 2 Structures of macrolide glycosides from marine cyanobacteria. 

No nucleotide derivatives of the macrolide sugars or their hypothetical precursors have yet been found which would support the proposed scheme. Therefore, it is possible that some of the final transformations of the macrolide sugars occur at the level of the preformed macrolide glycosides. 

Teruya, T, Sasaki, H Kitamura, K Nakayama, T, and Suenaga, K. (2009a) Biselyngbyaside, a macrolide glycoside from the marine cyanobacterium Lyngbya sp. Org. Lett., 11, 2421-2424. 

MacMillan, J.B., Xiong-Zhou, G Skepper, C.K., and Molinski, T.F. (2008) Phorbasides A-E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations. J. Org. Chem., 73, 3699-3706. 

Suenaga, K., Hoshino, H., Yoshii, X, Mori, K Sone, H Bessho, Y Sakakura, A Hayakawa, I., Yamada, K., and Kigoshi, H. (2006) Enatioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin. Tetrahedron, 62, 7687-7698. 

Erickson, K.L., Gustafson, K.R., Pannell, L.K., Beutler, JA., and Boyd, M.R. (2002) New dimeric macrolide glycosides from the marine sponge Myriastra davosa, J, Nat, Prod., 65,1303-1306. 

---