Synthesis of the reported structure of homocereulide and its vacuolation assay
Synthesis of the reported structure of homocereulide and its vacuolation assay
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DOI：
10.1016/j.bmcl.2019.01.007
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发表时间：
2019-03-01
影响因子：
2.7
通讯作者：
Tanimori, Shinji
中科院分区：
文献类型：
--
作者：
Naka, Toshihito;Hattori, Yoshihide;Tanimori, Shinji
Homocereulide是从海洋细菌蜡状芽孢杆菌中分离出来的，是催吐毒素cereulide的类似物。其结构确定及参与B的研究未见报道。与蜡有关的食物中毒高脑利是由L-O-Val-L-Val-D-O-Leu-D-Ala和L-O-allo-Ile-D-Val-D-O-Leu-D-Ala组成的环状十二肽。本文采用液相片段缩合法合成了高脑利。合成的高脑利的NMR谱证实了预期结构，LC-MS结果与天然产物一致。使用HEp-2细胞进行的形态学评价显示，高脑利（1.39 nM）的毒性高于催吐利（3.95 nM）。虽然催泪素是肉汤培养物中的主要成分，但高催泪素也可能参与B。与蜡有关的食物中毒
Homocereulide, isolated from marine bacterium Bacillus cereus, is an analog of emetic toxin cereulide. There is no report on its structure determination and involvement in B. cereus-associated food poisoning. Homocereulide is a cyclic dodecadepsipeptide composed of L-O-Val-L-Val-D-O-Leu-D-Ala and L-O-allo-Ile-D-Val-D-O-Leu-D-Ala. Here, we synthesized homocereulide using liquid phase fragment condensation. The NMR spectrum of synthesized homocereulide confirmed the intended structure and LC-MS results were consistent with natural products. Morphological evaluation using HEp-2 cells showed higher toxicity with homocereulide (1.39 nM) than cereulide (3.95 nM). Though cereulide is the main component in broth culture, homocereulide is also likely involved in B. cereus-associated food poisoning.