Discovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chain
Discovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chain
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DOI：
10.1002/ejoc.202300084
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发表时间：
2023-02-28
影响因子：
2.8
通讯作者：
Kita，Masaki
中科院分区：
文献类型：
--
作者：
Hioki，Yusuke;Sato，Tatsuya;Kita，Masaki
无壳草食性海洋软体动物（海兔）黑兔被认为含有多种生物活性物质。虽然这些化合物被认为起源于海藻或与之相关的微生物，但它们的大部分起源和获取途径仍不清楚。从黑田葵中分离到6个新的细胞毒性氨酮衍生物——溴多巴胺-萜类杂化分子。其中异丙氨酮在C15脂肪链上有一个反戊烯基，从萜类生物合成的角度来看，这是一个罕见的结构特征。化学成分的研究。kurodai和在几个不同地点收集的海藻显示，在特定的地点，劳伦西亚复合体物种中含有两种主要的applaminones。我们的化学和生态学研究为海洋生物碱毒素的起源及其在食物链中的动态提供了新的见解。
The shell‐less herbivorous marine mollusk (sea hare)Aplysia kurodaiis known to contain a variety of bioactive substances. While these compounds have been thought to originate from sea algae or their associated microbes, most of their origin and acquisition pathways are still unclear. Six new cytotoxic aplaminone derivatives, bromodopamine‐terpenoid hybrid molecules, were isolated fromA. kurodai. Among them, isoaplaminone had a reverse prenyl group at the C15 aliphatic chain, which is a rare structural feature from the viewpoint of terpenoid biosynthesis. Investigation for chemical components inA. kurodaiand the sea algae collected at several different locations revealed that two major aplaminones were contained in theLaurenciacomplex species at specific sites. Our chemical and ecological studies provide new insights into the origin of marine alkaloid toxins and their dynamism through the food chain.