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Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida).
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-07-03 , DOI: 10.3762/bjoc.16.132
Cora Hertzer 1 , Stefan Kehraus 1 , Nils Böhringer 2, 3 , Fontje Kaligis 4 , Robert Bara 4 , Dirk Erpenbeck 5, 6 , Gert Wörheide 5, 6, 7 , Till F Schäberle 2, 3 , Heike Wägele 8 , Gabriele M König 1
Affiliation  

Investigations on the biochemical relationship between Doriprismatica stellata (Chromodorididae, Doridoidea) nudibranchs, their egg ribbons, and the associated dietary sponge Spongia cf. agaricina (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 Doriprismatica and scalarane-containing dictyoceratid sponges of the Spongiidae family. The results also indicate that D. stellata passes the scalarane metabolite on to its egg ribbons, most likely for protective purposes. The scalarane showed antibacterial activity against the Gram-positive bacteria Arthrobacter crystallopoietes (DSM 20117) and Bacillus megaterium (DSM 32).

中文翻译:

Doriprismatica stellata nudibranchs(Gastropoda,Nudibranchia)的抗菌斯卡拉胶,鸡蛋带及其饮食海绵Spongia cf. 琼脂(Demospongiae,Dictyoceratida)。

对之间的生物化学关系调查Doriprismatica斯泰拉塔(Chromodorididae,Doridoidea)海蛞蝓,他们的鸡蛋丝带,以及相关的饮食海绵海绵Spongia比照 agaricina(Demospongiae,Porifera)导致分离出结构新的scalarane型酯基萜烯12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methyldeoxoscalarin,并且环丙烷环空前的位置与环退火答:与其他通常在环C的C-12上官能化的scalaranes不同,它在C-11和C-24上带有两个乙酰氧基。该化合物存在于所有三个样品中,支持多riprismatica属的嗜铬结节之间的饮食关系。以及海绵宝宝科的含有scalarane的双鳞cer海绵。研究结果还表明,D.斯泰拉塔传递给它的蛋丝带scalarane代谢产物,最有可能为保护目的。标量烷显示出对革兰氏阳性细菌结晶节杆菌(DSM 20117)和巨大芽孢杆菌(DSM 32)的抗菌活性。
更新日期:2020-07-03
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