Investigations of terpenoid biosynthesis by the dorid nudibranch Cadlina luteomarginata
Investigations of terpenoid biosynthesis by the dorid nudibranch Cadlina luteomarginata
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DOI：
10.1021/jo970695v
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发表时间：
1997-10-17
影响因子：
3.6
通讯作者：
Andersen, RJ
中科院分区：
文献类型：
--
作者：
Kubanek, J;Graziani, EI;Andersen, RJ
利用[1，2-C-13（2）]乙酸酯、[1，2-C-13（2），O-18（1）]乙酸酯、[1，2-C-13]甲羟戊酸内酯和[2-C-13]甲羟戊酸内酯的稳定同位素掺入研究了裸鳃海蛞蝓Cadlina luteomatata对萜类化合物乙酸白酯（1）、钙醛（2）和叶黄素（3）的生物合成。结果表明，所有三个萜类化合物是从头合成的C，luteomenatata和掺入模式是一致的生物成因的建议，即新的cadlinalane和luteane碳骨架的降解形成的二萜类化合物前体。这是海洋软体动物生物合成二倍半萜类化合物的第一个证明。定量分析表明，只有一个小的周转代谢物发生在喂养实验，但新形成的分子具有极高水平的掺入标记的前体。
Stable isotope incorporation studies with [1,2-C-13(2)]acetate, [1,2-C-13(2),O-18(1)]acetate, [1,2-C-13],mevalonolactone, and [2-C-13]mevalonolactone have been used to investigate the biosynthesis of the terpenoids albicanyl acetate (1), cadlinaldehyde (2), and luteone (3) by the dorid nudibranch Cadlina luteomarginata. The results have shown that all three terpenoids are synthesized de novo by C, luteomarginata and the incorporation patterns are consistent with the biogenetic proposal that the new cadlinalane and luteane carbon skeletons are formed by degradation of a sesterterpenoid precursor. This represents the first demonstration of sesterterpenoid biosynthesis by a marine mollusc. Quantitative analysis has shown that only a small turnover of metabolites takes place during the feeding experiments but that the newly formed molecules have extremely high levels of incorporation of labeled precursors.