4α-Acetoxyamijidictyol - A New Antifeeding Dolastane Diterpene from the Brazilian Brown Alga Canistrocarpus cervicornis

Éverson Miguel Bianco; Thiago Martins Francisco; Carlos Basílio Pinheiro; Rodrigo Bagueira de Vasconcellos Azeredo; Valéria Laneuville Teixeira; Renato Crespo Pereira

doi:10.1002/cbdv.201400410

4α-Acetoxyamijidictyol - A New Antifeeding Dolastane Diterpene from the Brazilian Brown Alga Canistrocarpus cervicornis

Chem Biodivers. 2015 Nov;12(11):1665-77. doi: 10.1002/cbdv.201400410.

Authors

Éverson Miguel Bianco^{1

2}, Thiago Martins Francisco³, Carlos Basílio Pinheiro³, Rodrigo Bagueira de Vasconcellos Azeredo⁴, Valéria Laneuville Teixeira^{4

5}, Renato Crespo Pereira^{4

5}

Affiliations

¹ Programa de Pós-graduação em Química, Departamento de Química, Fundação Universidade Regional de Blumenau, Campus 1, Bloco S, Victor Konder, CEP 89012-900, Blumenau, SC, Brazil, (phone: +55-47-33210615). ebianco@chemist.com.
² Programa de Pós-graduação em Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Baptista, Campus do Valonguinho, s/n, CEP 24020-150, Niterói, RJ, Brazil. ebianco@chemist.com.
³ Departamento de Física, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Campus da Pampulha, P. O. Box 702, 30123-970, Belo Horizonte, MG, Brazil.
⁴ Programa de Pós-graduação em Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Baptista, Campus do Valonguinho, s/n, CEP 24020-150, Niterói, RJ, Brazil.
⁵ Departamento de Biologia Marinha, Instituto de Biologia, Outeiro de São João Baptista, Campus do Valonguinho, s/n, P. O. Box 100.644, CEP 24001-970, Niterói, RJ, Brazil.

PMID: 26567945
DOI: 10.1002/cbdv.201400410

Abstract

Chemical investigation of the CH2 Cl2 crude extract from the brown alga Canistrocarpus cervicornis (Dictyotaceae) led to isolation of one new (1) and four previously reported dolastane diterpenes (2-5). Their structures were characterized by 1D- and 2D-NMR spectroscopic techniques, including a full single crystal X-ray diffraction analysis for 1, 2, and 4. In addition, the new structure 1 was assayed as chemical defense inhibiting the feeding by the sea urchin Lytechinus variegatus. This study constitutes an additional report broadening the known spectrum of action and defensive roles of secondary metabolites of the C. cervicornis and Dictyotales species.

Keywords: 4α-Acetoxyamijidictyol; Antifeeding; Canistrocarpus cervicornis; Dolastane diterpene.

MeSH terms

Animals
Brazil
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Feeding Behavior / drug effects*
Lytechinus / drug effects*
Models, Molecular
Molecular Conformation
Phaeophyceae / chemistry*

Substances

4alpha-acetoxyamijidictyol
Diterpenes