Theonezolides from Theonella

The theonezolides are 37-membered macrocycles, consisting of fatty acid chains with attached functionalities such as a sulfate ester and a thiazole [22]. Theonezolide A (610) is a cytotoxic metabolite of Theonella sp. from Okinawa. The structure was reported without stereochemical details [489]. The structures of theonezolides B (611) and C (612) from a Japanese Theonella sp. were determined by spectroscopic methods but without stereochemistry, except at one centre [490]. 

The theonezolides A-C (431-433) were isolated from the sponge Theonella sp. They are 37-membered macrocyclic compounds consisting of two principal fatty acid chains with various functionalities such as a sulfate ester, an oxazole, and a thiazole [336, 337]. Compounds 431-433 displayed cytotoxic activity against L1210 and KB cells and were found to have a unique bioactivity in terms of induction of rabbit platelet shape change and aggregation [338]. 

Rho, M.-C., Park, Y.-H., Sasaki, S., Ishibashi, M., Kondo, K., Kobayashi, J., and Ohizumi, Y. (1996). The mode of rabbit platelet shape change and aggregation induced by theonezolide-A, a novel polyketide macroUde, isolated from the Okinawan marine sponge Theonella sp. Can. J. Physiol. Pharmacol. 74,193-199. 

Two additional macrolides, theonezolides B (127) and C (128), were also isolated from the same Okinawan marine sponge Theonella sp., and their structures were elucidated on the basis of spectroscopic data as well as chemical degradation experiments [77]. Altihough the H NMR spectra of theonezolides B (127) and C (128) appeared almost indistinguishable to... 

---