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Molecules 2014, 19(3), 3181-3192;

Sesquiterpenes from the Brazilian Red Alga Laurencia dendroidea J. Agardh

Instituto de Química, Universidade Federal do Rio de Janeiro, Avenida Athos da Silveira Ramos, 149, 21941-909, Rio de Janeiro, RJ, Brazil
Grupo de Produtos Naturais de Organismos Aquáticos (GPNOA), Núcleo de Estudos em Ecologia e Desenvolvimento Sócioambiental de Macaé, Universidade Federal do Rio de Janeiro – Campus Macaé, Av. São José do Barreto, 764, 27965-045, Macaé, RJ, Brazil
Laboratório de Biologia do Reconhecer, Centro de Biociências e Biotecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Avenida Alberto Lamego, 2000, 28013-602, Campos dos Goytacazes, RJ, Brazil
Laboratório de Algas Marinhas Professor Édison José de Paula, Departamento de Botânica, Universidade de São Paulo, Rua do Matão, 277, 05508-090, São Paulo, SP, Brazil
Laboratório Regional de Difração de Raios X (LDRX), Universidade Federal Fluminense, Avenida Litorânea, s/n, 24020-150, Niterói, RJ, Brazil
Laboratório de Produtos Naturais, Curso de Farmácia, Universidade Federal do Rio de Janeiro, Campus Macaé, Pólo Novo Cavaleiro – IMMT, Rua Alcides da Conceição, 159, 27933-378, Macaé, RJ, Brazil
Author to whom correspondence should be addressed.
Received: 15 January 2014 / Revised: 3 March 2014 / Accepted: 5 March 2014 / Published: 17 March 2014
(This article belongs to the Section Natural Products Chemistry)
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Two new chamigrane sesquiterpenes 12 and three known compounds 35 were isolated from a lipophilic extract of the red alga Laurencia dendroidea collected from the Southeastern Brazilian coast. Dendroidone (1) and dendroidiol (2) were isolated from samples collected at Biscaia Inlet, Angra dos Reis, Rio de Janeiro and at Manguinhos Beach, Serra, Espírito Santo, respectively. Debromoelatol (3), obtusane (4) and (1S*,2S*,3S*,5S*,8S*,9S*)-2,3,5,9-tetramethyltricyclo[]undecan-2-ol (5) were obtained from specimens collected at Vermelha Beach, Parati, Rio de Janeiro. The structures of new compounds were elucidated by extensive NMR (1H-, 13C-, COSY, HSQC, HMBC and NOESY) and high resolution mass spectrometry analysis. Additionally, the absolute configuration of compound 2 was assigned by X-ray analysis. Full spectroscopic data is described for the first time for compound 3. Anti-inflammatory and antimycobacterial activities of compounds 25 were evaluated. Compounds 35 inhibited the release of inflammatory mediator NO while TNF-α levels were only affected by 3. All compounds tested displayed moderate antimycobacterial action. View Full-Text
Keywords: chamigrane; Laurencia dendroidea; anti-inflammatory; antimycobacterial chamigrane; Laurencia dendroidea; anti-inflammatory; antimycobacterial

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da Silva Machado, F.L.; Ventura, T.L.B.; Gestinari, L.M.S.; Cassano, V.; Resende, J.A.L.C.; Kaiser, C.R.; Lasunskaia, E.B.; Muzitano, M.F.; Soares, A.R. Sesquiterpenes from the Brazilian Red Alga Laurencia dendroidea J. Agardh. Molecules 2014, 19, 3181-3192.

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