Hertzer Cora, Kehraus Stefan, Böhringer Nils, Kaligis Fontje, Bara Robert, Erpenbeck Dirk, Wörheide Gert, Schäberle Till F, Wägele Heike, König Gabriele M
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
Institute for Insect Biotechnology, Justus-Liebig-University, Heinrich-Buff-Ring 26-32, 35392 Gießen, Germany.
Beilstein J Org Chem. 2020 Jul 3;16:1596-1605. doi: 10.3762/bjoc.16.132. eCollection 2020.
Investigations on the biochemical relationship between (Chromodorididae, Doridoidea) nudibranchs, their egg ribbons, and the associated dietary sponge cf. (Demospongiae, Porifera) led to the isolation of the structurally new scalarane-type sesterterpene 12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methylenedeoxoscalarin, with an unprecedented position of the cyclopropane ring annelated to the ring A. Unlike other scalaranes, which are most often functionalized at C-12 of ring C, it bears two acetoxy groups at C-11 and C-24 instead. The compound was present in all three samples, supporting the dietary relationship between chromodorid nudibranchs of the genus and scalarane-containing dictyoceratid sponges of the Spongiidae family. The results also indicate that passes the scalarane metabolite on to its egg ribbons, most likely for protective purposes. The scalarane showed antibacterial activity against the Gram-positive bacteria (DSM 20117) and (DSM 32).
对（多彩海牛科，裸鳃亚目）裸鳃类动物、它们的卵带以及相关的食源海绵cf.（寻常海绵纲，多孔动物门）之间生化关系的研究，导致分离出结构新颖的四环三萜型倍半萜烯12 - 脱乙酰氧基 - 4 - 去甲基 - 11,24 - 二乙酰氧基 - 3,4 - 亚甲基二氧四环三萜，其环丙烷环与A环稠合的位置前所未有的。与其他四环三萜不同，其他四环三萜最常在C环的C - 12位官能化，而它在C - 11和C - 24位带有两个乙酰氧基。该化合物存在于所有三个样品中，支持了该属多彩海牛裸鳃类动物与海绵科含四环三萜的网角海绵之间的食源关系。结果还表明，它将四环三萜代谢物传递给其卵带，很可能是出于保护目的。该四环三萜对革兰氏阳性菌（DSM 20117）和（DSM 32）显示出抗菌活性。
