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J Nat Prod. 2017 Nov 22;80(11):3049-3053. doi: 10.1021/acs.jnatprod.7b00510. Epub 2017 Nov 7.

Isolation of Chamigrene Sesquiterpenes and Absolute Configuration of Isoobtusadiene from the Brittle Star Ophionereis reticulata.

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CNR, Istituto di Chimica Biomolecolare, Bio-Organic Chemistry Unit , 80078 Pozzuoli, Naples, Italy.
Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará , 60021-970, Fortaleza, CE, Brazil.
Departamento de Biologia, Centro de Ciências, Universidade Federal do Ceará , 60021-970, 60455-760, Fortaleza, CE, Brazil.
Departamento de Farmacologia, Instituto de Ciências Biomédicas, Universidade de São Paulo , 05508-010 São Paulo, SP, Brazil.
Instituto Federal de Educação, Ciência e Tecnologia , 63475-000, Jaguaribe, CE, Brazil.


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.

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