Sesquiterpene furans and thiosesquiterpenes from the nudibranch Ceratosoma brevicaudatum.
Sesquiterpene furans and thiosesquiterpenes from the nudibranch Ceratosoma brevicaudatum.
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来自裸鳃类动物 Ceratosoma brevicaudatum 的倍半萜呋喃和硫代倍半萜。
DOI：
10.1021/np50059a007
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发表时间：
1988
影响因子：
5.1
通讯作者：
Schmitz,FJ
中科院分区：
文献类型：
--
作者：
Ksebati,MB;Schmitz,FJ
裸鳃类动物的防御策略之一是从海绵食物中提取代谢物作为化学防御剂（1-3）。在报道的同化防御化学物质中包括多种萜烯代谢物。最近，我们报道了从几种裸鳃类动物中分离出一组海绵烷二萜（4）。随后，我们从同一地区收集了另一批裸鳃类动物，这些动物已被鉴定（提取合并批次后）为Ch. epicuria和Ce的混合集合。短尾状，后者占优势。少年队。在野外，短尾虫看起来与Ch. epicuria（以及其他几个物种）非常相似，因此，在采集时进行表面检查时，所有标本都被认为是同一物种。从裸鳃类的混合标本中，我们分离出三种已知的呋喃基萜类化合物：脱氢树酯萜[1]（5）、脱氢树酯萜[3]（6，7）、硫代呋喃基乙酸酯萜[7]（8-10），以及三种新的呋喃基萜类化合物：2、4和5。首次从一种未鉴定的海绵Dysidea sp.中分离到一种非常罕见的含硫倍半萜7。（8，9），并且最近再次从Dysidea avara中发现，其中它与游离硫醇一起8（10）。这些化合物和相关的thiofurudysin acetate似乎是迄今为止报道的唯一天然存在的萜烯硫醇衍生物（8）。
One of the defense strategies for nudibranchs involves the sequestering of metabo-lites from their sponge diet as chemical defense agents (1—3). Included among the re-ported assimilateddefensive chemicals are a variety of terpene metabolites. Recently, we reported the isolation of a group of spongiane diterpenes from several nudibranchs [tentatively identifiedthen as Ceratosoma brevicaudatum (Abraham, 1876; Chromodorididae), but now corrected to Chromodoris epicuria (Basedow and Hedley)] that were col-lected near Adelaide, South Australia (4). Subsequently, we collected another batch of nudibranchs from the same area and these have been identified (after extraction of the combined batch) as a mixed collection of Ch. epicuria and Ce. brevicaudatum with the lat-ter predominating. Juvenile Ce. brevicaudatum look very similar to Ch. epicuria (and to several other species) in the field, and, consequently, upon superficial examination at the time of collection all specimens were thought to be of the same species. From this mixed collection of nudibranchs we have isolated three known furanosesqui terpenes, dehydrodendrolasin [1](5), dehydrolasiosperman [3](6, 7), thiofurodysinin acetate [7](8—10), andthree new furanosesqui terpenes, 2, 4, and 5. The very uncommon sulfurcontaining sesquiterpene 7 was isolated first from an unidentified species of sponge, Dysidea sp.(8, 9), and again recently from Dysidea avara where it was found together with the free thiol 8 (10). These compounds and the related thiofurodysin acetate ap-pear to be the only naturally occurring terpene thiol derivatives reported to date (8).