title: Chemical profile and biological potential of non-polar fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta).
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 IC(50) = 19.1 μg.mL-1 and trypomastigote IC(50) = 76.2 μg.mL-1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 μg) by TLC-bioautography.
authors.affiliation: 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.
authors.forename: Otávio P
authors.initials: OP
authors.lastname: Rocha
authors.forename: Rafael
authors.initials: R
authors.lastname: De Felício
authors.forename: Ana Helena B
authors.initials: AH
authors.lastname: Rodrigues
authors.forename: Daniela L
authors.initials: DL
authors.lastname: Ambrósio
authors.forename: Regina Maria B
authors.initials: RM
authors.lastname: Cicarelli
authors.forename: Sérgio
authors.initials: S
authors.lastname: De Albuquerque
authors.forename: Maria Claudia M
authors.initials: MC
authors.lastname: Young
authors.forename: Nair S
authors.initials: NS
authors.lastname: Yokoya
authors.forename: Hosana M
authors.initials: HM
authors.lastname: Debonsi
mesh_terms: D014355:Chagas Disease / Q000188:drug therapy / Q000469:parasitology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002963:Cladosporium / Q000187:drug effects* / Q000254:growth & development; D005227:Fatty Acids / Q000737:chemistry / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D006586:Hexanes / Q000737:chemistry; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008752:Methylene Chloride / Q000737:chemistry; D009181:Mycoses / Q000188:drug therapy / Q000382:microbiology; D019308:Palmitic Acid / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D000461:Rhodophyta / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013045:Species Specificity; D014349:Trypanosoma cruzi / Q000187:drug effects* / Q000254:growth & development
chemical_list: D005227:Fatty Acids; D006586:Hexanes; D010936:Plant Extracts; D012997:Solvents; D019308:Palmitic Acid; D008752:Methylene Chloride; C117025:pentadecanoic acid