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      Estudo da atividade antioxidante do extrato e do óleo essencial obtidos das folhas de alfavaca (Ocimum gratissimum L.) Translated title: Study of the antioxidant activity and essential oil from wild basil (Ocimum gratissimum L.) leaf

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          Abstract

          O isolamento e a identificação de antioxidantes naturais, extraídos de plantas, contribuem para a descoberta de novas fontes de compostos químicos. A alfavaca (Ocimum gratissimum L.) é uma planta conhecida por seus aspectos medicinais e pelo uso na culinária. A atividade antioxidante do extrato bruto e do óleo essencial das folhas de alfavaca foi comprovada através do método do tiocianato férrico. A porcentagem de inibição da oxidação lipídica foi de 96,89% para o extrato bruto e de 92,44% para o óleo essencial, ambos na concentração de 0,02%. O extrato bruto foi purificado através da cromatografia em coluna com sílica-gel e fase móvel hexano:acetato de etila em diferentes proporções. Para a identificação, foram utilizadas análises espectrais (infravermelho, ressonância magnética de hidrogênio e carbono 13). A substância isolada foi o eugenol, que apresentou 86,56% de atividade antioxidante. Alguns constituintes do óleo essencial foram caracterizados por cromatografia de fase gasosa, sendo o eugenol o principal componente (53,90%). Desta forma, a alfavaca apresenta-se como uma nova fonte de eugenol e, conseqüentemente, de antioxidante natural.

          Translated abstract

          The isolation and identification of natural antioxidants from plants contribute to the discovery of new sources of chemical compounds. Wild basil (Ocimum gratissimum L.) is used as a herbal medicine and also as a culinary spice. The antioxidant activity of wild basil leaf crude extract and essential oil was confirmed by the ferric thiocyanate method. The crude extract showed 96.89% inhibition of lipid oxidation, while the essential oil showed 92.44% inhibition, both in a 0.02% concentration. The crude extract was purified by column chromatography using silica gel and different proportions of hexane:ethyl acetate as an eluant. The plant’s chemical compounds were identified by spectral analyses using NMR (hydrogen and 13C) and infrared spectroscopy. The isolated substance was eugenol, which presented antioxidant activity of 86.56%. Some of the constituents of the essential oil were characterized by gas chromatography, which showed eugenol as the main component (53.90%). It was concluded that wild basil is a new source of eugenol and, hence, of natural antioxidant.

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          Composition and antimicrobial activity of essential oils from aromatic plants used in Brazil

          Essential oils from aerial parts of Mentha piperita, M. spicata, Thymus vulgaris, Origanum vulgare, O. applii, Aloysia triphylla, Ocimum gratissimum, O. basilicum were obtained by steam destillation using a Clevenger-type system. These oils were screened for antibacterial and anti-Candida albicans activity using bioautographic method. Subsequently, minimal inhibitory concentration from oils was determined by microdilution method. Most essential oil studied were effective against Enterococcus faecium and Salmonella cholerasuis. Aloysia triphylla and O. basilicum presented moderate inhibition against Staphylococcus aureus while only A. tryphila and M. piperita were able to control the yeast Candida albicans. The oils were analyzed by GC and GC-MS techniques in order to determine the majoritary compounds.
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            Characterization of the volatile pattern and antioxidant capacity of essential oils from different species of the genus Ocimum.

            The antioxidant capacity of essential oils obtained by steam hydrodistillation from five species of the genus Ocimum, namely Ocimum basilicum var. purpurascens, Ocimum basilicum, Ocimum gratissimum, Ocimum micranthum, and Ocimum tenuiflorum (syn. O. sanctum), were evaluated using a high-performance liquid chromatography-based hypoxanthine/xanthine oxidase and the DPPH assays. The yield of oils from the leaves of the five species was variable with the greater amount obtained from Ocimum gratissimum (3.5%) and the least from Ocimum basilicum var. purpurascens (0.5%). In the hypoxanthine/xanthine oxidase assay, strong antioxidant capacity was evident in all the oils but the greater was shown by that obtained from Ocimum tenuiflorum (syn. O. sanctum) (IC50 = 0.46 microL/mL) compared to Ocimum basilicum var. purpurascens (IC50 = 1.84 microL/mL). Antioxidant capacity was positively correlated (r = 0.92, p 0.1) with other major volatiles was observed. These correlations were confirmed to a large extent in the DPPH assay. The results of a 24 h experiment with Ocimum tenuiflorum (syn. O. sanctum) shows that the antioxidant capacity factor (amount of essential oil obtained x free radical scavenging capacity; mg x %/100) reaches a threshold between 10 and 12.00 h, corresponding to maximum sunlight intensity in Brasil and furthermore exhibits a clear diurnal variation. The data generated with Ocimum species indicates that essential oils obtained from various herbs and spices may have an important role to play in cancer chemoprevention, functional foods, and in the preservation of pharmacologic products.
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              The metabolism of eugenol in man

              1. The metabolism of eugenol (4-hydroxy-3-methoxy-allylbenzene) was investigated in male and female healthy volunteers. It was rapidly absorbed and metabolized after oral administration and was almost completely excreted in the urine within 24 h. Unmetabolized eugenol excreted in urine amounted to less than 0.1% of the dose. 2. The urine contained conjugates of eugenol and of nine metabolites. The structures of these metabolites, elucidated using g.l.c.-mass spectrometry, and by comparison with synthetic reference compounds, were identified as: eugenol, 4-hydroxy-3-methoxyphenyl-propane, cis- and trans-isoeugenol, 3-(4-hydroxy-3-methoxyphenyl)-propylene-1,2-oxide, 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol, and 3-(4-hydroxy-3-methoxyphenyl)-propionic acid. 3. The structures of the following metabolites were tentatively deduced from mass spectra only, as reference compounds were not available: 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-allylbenzene, 3-(6?-mercapto-4-hydroxy-3-methoxyphenyl)-propane, and 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-propionic acid. 4. The amounts of the individual metabolites excreted were determined by g.l.c. Some 95% of the dose was recovered in the urine, most of which (greater than 99%) consisted of phenolic conjugates; 50% of the conjugated metabolites were eugenol-glucuronide and sulphate. Other metabolic routes observed were the epoxide-diol pathway, synthesis of a thiophenol and of a substituted propionic acid, allylic oxidation, and migration of the double bond.
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                Author and article information

                Contributors
                Role: ND
                Role: ND
                Journal
                cta
                Food Science and Technology (Campinas)
                Food Sci. Technol (Campinas)
                Sociedade Brasileira de Ciência e Tecnologia de Alimentos (Campinas )
                1678-457X
                September 2007
                : 27
                : 3
                : 624-632
                Affiliations
                [1 ] Universidade Federal de Viçosa Brazil
                [2 ] Centro Universitário Central Paulista Brazil
                [3 ] Centro Universitário Vila Velha Brasil
                Article
                S0101-20612007000300030
                10.1590/S0101-20612007000300030
                a940e5fc-00c8-45d7-9576-2cb8036cc604

                http://creativecommons.org/licenses/by/4.0/

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                SciELO Brazil

                Self URI (journal page): http://www.scielo.br/scielo.php?script=sci_serial&pid=0101-2061&lng=en
                Categories
                FOOD SCIENCE & TECHNOLOGY

                Food science & Technology
                antioxidant,eugenol,wild basil,lipid oxidation,antioxidante,alfavaca,oxidação lipídica

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