Egami Yoko, Wakimoto Toshiyuki, Abe Ikuro
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Bioorg Med Chem Lett. 2014 Nov 15;24(22):5150-3. doi: 10.1016/j.bmcl.2014.10.002. Epub 2014 Oct 13.
Calyculin C, a minor derivative of the calyculins, has an additional methyl group on C32 of calyculin A. A recent biosynthetic study of calyculins revealed that an end product of calyculin biosynthesis is the pyrophosphate form, phosphocalyculin A. However, the pyrophosphate counterpart derived from calyculin C had not been reported. We isolated phosphocalyculin C as a minor pyrophosphate derivative, by a detailed investigation of an extract from the sponge Discodermia calyx. The treatment of phosphocalyculin C with the D. calyx cell-free extract significantly enhanced its cytotoxicity, providing molecular evidence for its role as the protoxin of calyculin C.
刺尾鱼毒素C是刺尾鱼毒素的一种次要衍生物，在刺尾鱼毒素A的C32位上有一个额外的甲基。最近对刺尾鱼毒素的生物合成研究表明，刺尾鱼毒素生物合成的最终产物是焦磷酸形式的磷酸刺尾鱼毒素A。然而，源自刺尾鱼毒素C的焦磷酸类似物尚未见报道。我们通过对海绵皮海绵提取物的详细研究，分离出了作为次要焦磷酸衍生物的磷酸刺尾鱼毒素C。用皮海绵无细胞提取物处理磷酸刺尾鱼毒素C可显著增强其细胞毒性，为其作为刺尾鱼毒素C的原毒素的作用提供了分子证据。
