Isolation and structures of Theonezolides B and C from the Okinawan marine sponge Theonella sp.

✍ Scribed by Kazuhiko Kondo; Masami Ishibashi; Jun'ichi Kobayashi

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 612 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85558-7

✦ Synopsis

Theowpolide B (2) end C (J), hvo new macrolidea with vclrious functionalitiea, have beon isolated from theOkinawpnm;rrine8pongeI)uoncllasp.rmdtbeirstrucbneselucidatsdonthsbrsisof~ icdahcls well= chemical degrndstion e.x~ts. Ths absoh confiSur&ms oftha tehnal chirai centerof~lides A (l), B (2), and C (3) wcxe delermined by synthesis of their ozunolysis products. During our studies on bioactive substances from Okinawaa marine organisms,1 we recently isolated a novel macrolide, theonezolide A (l), from the Okinawan marine sponge TheoneZlla sp? Theonezolide A (1) belongs to a new class of polyketide nahnal products, consisting of two princiPal fatly acid chains with various functional groups. Further investigation on extracts of this sponge has now resulted in isolation of two new related macrolides, theonezolides B (2) and C (3), with relatively considerable abundance. Here we describe the isolation and structure elucidation of 2 and 3. Theonezolides A (l), B (2), and C (3) possess a chii centerwithaprimaryaminogroupatthe~position,andthispapeaalsodealswiththedetenninationof the absolute configmations of the krminal chiral centers of 1 -3 on the basis of synthesis of one of their ozonolysis products @a, 8b, and 8~).