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次生代谢组及其在海兔亚目(腹足纲、异鳃亚纲、裸鳃目)中的防御作用。

Secondary metabolome and its defensive role in the aeolidoidean , (Gastropoda, Heterobranchia, Nudibranchia).

作者信息

Bogdanov Alexander, Hertzer Cora, Kehraus Stefan, Nietzer Samuel, Rohde Sven, Schupp Peter J, Wägele Heike, König Gabriele M

机构信息

Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.

Institute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, Germany.

出版信息

Beilstein J Org Chem. 2017 Mar 13;13:502-519. doi: 10.3762/bjoc.13.50. eCollection 2017.

Abstract

is the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids , cembranoid diterpenes , complex biscembranoids and , and the chatancin-type diterpenes . These compounds resemble those from soft corals of the genus , of which to date, however, only is described as a food source for . Fish feeding deterrent activity was determined using the tropical puffer fish , and showed activity for (2)-isosarcophytoxide (), cembranoid bisepoxide and 4-oxochatancin (). Determining the metabolome of and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal.

摘要

是迄今为止已知的最大的海兔科物种,并且在萜类化学方面极其丰富。在此我们报告从该物种的单个标本中总共分离出19种次生代谢产物,即甾体、西松烷型二萜、复杂的双西松烷类化合物以及查坦辛型二萜。这些化合物类似于来自属软珊瑚的那些化合物,然而,迄今为止,只有被描述为的食物来源。使用热带河豚测定了鱼类摄食威慑活性,并且显示(2)-异肉珊瑚毒素()、西松烷型双环氧化物和4-氧代查坦辛()具有活性。确定的代谢组及其生物活性表明,这种看似脆弱的软体动物通过其化学武器库能很好地抵御鱼类。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/783b/5372768/ae4304f03840/Beilstein_J_Org_Chem-13-502-g002.jpg

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