Structure and Stereochemistry of a New Cytotoxic Polychlorinated Sulfolipid from Adriatic Shellfish

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• 作者：Patrizia Ciminiello ; Carmela Dell'Aversano ; Ernesto Fattorusso ; Martino Forino ; Silvana Magno ; Massimo Di Rosa ; Angela Ianaro ; and Roberto Poletti
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：November 6, 2002
• 年：2002
• 卷：124
• 期：44
• 页码：13114 - 13120
• 全文大小：156K
• 年卷期：v.124,no.44(November 6, 2002)
• ISSN：1520-5126

文摘

A detailed analysis of the causative toxins contained in the hepatopancreas of toxic musselsfrom the northern Adriatic sea has been carried out. Along with some DSP (diarrhetic shellfish poisoning)type toxins, such as okadaic acid, yessotoxin, and their derivatives, which are involved in a number ofhuman intoxications throughout the world, we have now isolated a new cytotoxin, a polychlorinated sulfolipid1, whose gross structure has been elucidated by spectral analysis, including various 2D NMR techniques.The relative stereochemistry of 1 was elucidated by successful application of the J-based configurationanalysis developed for acyclic compounds using carbon-proton spin-coupling constants (^2,3J_C,H) and proton-proton spin-coupling constants (³J_H,H); its absolute stereochemistry was established by the Mosher method.Compound 1 possesses in vitro cytotoxicity against WEHI 164 and RAW 264.7 cells.