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Molecules 2011, 16(8), 7105-7114; doi:10.3390/molecules16087105
Article

Chemical Profile and Biological Potential of Non-Polar Fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta)

1, 1, 1, 2, 2, 3, 4, 5 and 1,*
1 Departamento de Física e Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto – USP, Av. do Café, s/n, CEP 14040-903, Monte Alegre, Ribeirão Preto-SP, Brazil 2 Faculdade de Ciências Farmacêuticas de Araraquara, Departamento de Ciências Biológicas – UNESP, Rodovia Araraquara-Jaú, Km 01. CEP 14801-902, Araraquara-SP, Brazil 3 Departamento de Análises Clínicas, Toxicológicas e Bromatológicas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto – USP, Av. do Café, s/n, CEP 14040-903, Monte Alegre, Ribeirão Preto-SP, Brazil 4 Núcleo de Pesquisas em Fisiologia e Bioquímica Vegetal, Instituto de Botânica, Secretaria de Estado do Meio Ambiente de São Paulo, Av. Miguel Estefano, 3687, Água Funda, CEP 04301-012, São Paulo-SP, Brazil 5 Núcleo de Pesquisas em Ficologia, Instituto de Botânica, Secretaria de Estado do Meio Ambiente de São Paulo, Av. Miguel Estefano, 3687, Água Funda, CEP 04301-012, São Paulo-SP, Brazil
* Author to whom correspondence should be addressed.
Received: 18 June 2011 / Revised: 3 August 2011 / Accepted: 8 August 2011 / Published: 19 August 2011
(This article belongs to the collection Bioactive Compounds)
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Abstract

The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). The main constituents of the fractions were hexadecanoic acid (17.6%) and pentadecanoic acid (15.9%). Several secondary metabolites with interesting biological activity, such as (-)-loliolide, neophytadiene, phytol were identified. In addition, several classes of secondary metabolites, including phenolic compounds (e.g., phenylacetic acid), terpene derivatives, fatty acids, halogenated compound (e.g., 2-chlorocyclohexenol), lignoids, steroids, esters, amides (e.g., hexadecanamide), ketones, carboxylic acids, aldehydes and alcohols were observed. The occurrence of several of these structural classes is described for the first time in this species. The same fractions analyzed by GC-MS, and a separate set of polar fractions, were evaluated against two life cycle stages (epimastigote and trypomastigote forms) of the protozoan Trypanosoma cruzi and against phytopatogenic fungi Cladosporium cladosporiodes and C. sphaerospermum. The dichloromethane fraction was active against both T. cruzi forms (epimastigote IC50 = 19.1 μg.mL−1 and trypomastigote IC50 = 76.2 μg.mL−1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 μg) by TLC-bioautography.
Keywords: Centroceras clavulatum; GC-MS analysis; Rhodophyta; trypanocidal activity; antifungal activity Centroceras clavulatum; GC-MS analysis; Rhodophyta; trypanocidal activity; antifungal activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Rocha, O.P.; Felício, R.D.; Rodrigues, A.H.B.; Ambrósio, D.L.; Cicarelli, R.M.B.; Albuquerque, S.D.; Young, M.C.M.; Yokoya, N.S.; Debonsi, H.M. Chemical Profile and Biological Potential of Non-Polar Fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta). Molecules 2011, 16, 7105-7114.

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