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Deprecated: Implicit conversion from float 302.79999999999995 to int loses precision in C:\Inetpub\vhosts\kidney.de\httpdocs\pget.php on line 534 Chemistry 2016 ; 22 (24): 8158-66 Nephropedia Template TP
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Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria #MMPMID27139508
Gunasekera SP; Li Y; Ratnayake R; Luo D; Lo J; Reibenspies JH; Xu Z; Clare-Salzler MJ; Ye T; Paul VJ; Luesch H
Chemistry 2016[Jun]; 22 (24): 8158-66 PMID27139508show ga
A new dimeric macrolide xylopyranoside, cocosolide (1), was isolated from the marine cyanobacterium preliminarily identified as Symploca sp. from Guam. The structure was determined by a combination of NMR, HRMS, X-ray diffraction studies and Mosher?s analysis of the base hydrolysis product. Its carbon skeleton closely resembles that of clavosolides A?D isolated from the sponge Myriastra clavosa, for which no bioactivity is known. We performed the first total synthesis of cocosolide (1) along with its [?,?]-anomer (26) and macrocyclic core (28), thus leading to the confirmation of the structure of natural 1. The convergent synthesis featured Wadsworth?Emmons cyclopropanation, Sakurai annulation, Yamaguchi macrocyclization/dimerization reaction, ?-selective glycosidation and ?-selective glycosidation. Compounds 1 and 26 potently inhibited IL-2 production in both T-cell receptor dependent and independent manners. Full activity requires the presence of the sugar moiety as well as the intact dimeric structure. Cocosolide (1) also suppressed the proliferation of anti-CD3-stimulated T-cells in a dose-dependent manner.