Isolation of Chamigrene Sesquiterpenes and Absolute Configuration of Isoobtusadiene from the Brittle Star Ophionereis reticulata,Journal of Natural Products

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Isolation of Chamigrene Sesquiterpenes and Absolute Configuration of Isoobtusadiene from the Brittle Star Ophionereis reticulata
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00510
Genoveffa Nuzzo ₁ , Bruno A. Gomes ₂ , Pietro Amodeo ₁ , Helena Matthews-Cascon ₃ , Adele Cutignano ₁ , Leticia V. Costa-Lotufo ₄ , Felipe A. C. Monteiro ₅ , Otilia Deusdenia L. Pessoa ₂ , Angelo Fontana ₁

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The chemical study of the Brazilian brittle star Ophionereis reticulata led to the isolation of three chamigrene sesquiterpenes, including the partially characterized isoobtusadiene (1), its unreported acetyl derivative (2), and the known (+)-elatol (3). The complete elucidation of the structures 1 and 2 was accomplished by 1D and 2D NMR spectroscopy. The first assignment of the absolute configuration of the isoobtusadiene skeleton is suggested as 6S,9R,10S on the basis of the NMR analysis of the Mosher’s ester derivatives of 1 and the ECD study of the acetyl derivative 2. Chamigrenes are typical constituents of Laurencia red algae. O. reticulata is a predator with a preference for algae. Thus, the origin of these metabolites can be likely ascribed to diet.

中文翻译：

脆性星状网眼番茄中香米黄酮倍半萜的分离和异obtusadiene的绝对构型

对巴西脆性星星网眼Ophionereis reticulata的化学研究导致分离出三个香米草倍半萜，包括部分表征的异obtusadiene（1），其未报告的乙酰基衍生物（2）和已知的（+）-elatol（3）。通过1D和2D NMR光谱可以完全阐明结构1和2。根据对1的Mosher酯衍生物的NMR分析和对乙酰基衍生物的ECD研究，建议将异obtusadiene骨架的绝对构型的第一个分配为6 S，9 R，10 S2。变种是劳伦西亚红藻的典型成分。O. reticulata是一种捕食者，偏爱藻类。因此，这些代谢产物的来源很可能归因于饮食。

更新日期：2017-11-07

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