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      Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives

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          Abstract

          ABSTRACT Considering the reported activity of carvone in the literature, this study aimed to evaluate the antimicrobial, cytotoxic and chemopreventive activities of (+)- and (-)-carvone, (+)- and (-)- hydroxydihydrocarvone and α,β-epoxycarvone. (+)-Hydroxydihydrocarvone (HC+), (-)-hydroxydihydrocarvone (HC-) and α,β-epoxycarvone (EP) were obtained by synthesis using (+)-carvone (C+) or (-)-carvone (C-) as precursors. The antifungal activity (MIC and MFC) were evaluated against Candida parapsilosis, C. tropicalis, C. krusei and C. albicans and the antibacterial activity (MIC and MBC) against Escherichia coli and Staphylococcus aureus. The cytotoxicity assays were performed with human cancer cell lines HepG-2 and SiHa and the normal strain MRC-5 through sulphorrodamine B assay. Chemoprevention was evaluated through quinone reductase assay. Our results showed no cytotoxicity on tumor and normal cell lines and no induction of the quinone reductase enzyme. C- and HC- presented activity against E. coli. All compounds presented weak antifungal activity against C. tropicalis and C. parapsilosis. EP and C+ showed moderate activity against C. krusei. Results suggest the potential use of carvones and its derivatives as antifungal agents against Candida yeasts. The absence of cytotoxicity in cell lines indicates safety in the use of these compounds.

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          New colorimetric cytotoxicity assay for anticancer-drug screening.

          We have developed a rapid, sensitive, and inexpensive method for measuring the cellular protein content of adherent and suspension cultures in 96-well microtiter plates. The method is suitable for ordinary laboratory purposes and for very large-scale applications, such as the National Cancer Institute's disease-oriented in vitro anticancer-drug discovery screen, which requires the use of several million culture wells per year. Cultures fixed with trichloroacetic acid were stained for 30 minutes with 0.4% (wt/vol) sulforhodamine B (SRB) dissolved in 1% acetic acid. Unbound dye was removed by four washes with 1% acetic acid, and protein-bound dye was extracted with 10 mM unbuffered Tris base [tris (hydroxymethyl)aminomethane] for determination of optical density in a computer-interfaced, 96-well microtiter plate reader. The SRB assay results were linear with the number of cells and with values for cellular protein measured by both the Lowry and Bradford assays at densities ranging from sparse subconfluence to multilayered supraconfluence. The signal-to-noise ratio at 564 nm was approximately 1.5 with 1,000 cells per well. The sensitivity of the SRB assay compared favorably with sensitivities of several fluorescence assays and was superior to those of both the Lowry and Bradford assays and to those of 20 other visible dyes. The SRB assay provides a colorimetric end point that is nondestructive, indefinitely stable, and visible to the naked eye. It provides a sensitive measure of drug-induced cytotoxicity, is useful in quantitating clonogenicity, and is well suited to high-volume, automated drug screening. SRB fluoresces strongly with laser excitation at 488 nm and can be measured quantitatively at the single-cell level by static fluorescence cytometry.
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            Characterization of the Action of Selected Essential Oil Components on Gram-Negative Bacteria

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              Antibacterial activity of Cuminum cyminum L. and Carum carvi L. essential oils.

              Essential oils extracted by hydrodistillation from fruits of Cuminum cyminum L. and Carum carvi L. were analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). The main components of C. cyminum oil were p-mentha-1,4-dien-7-al, cumin aldehyde, gamma-terpinene, and beta-pinene, while those of the C. carvi oil were carvone, limonene, germacrene D, and trans-dihydrocarvone. Antibacterial activity, determined with the agar diffusion method, was observed against Gram-positive and Gram-negative bacterial species in this study. The activity was particularly high against the genera Clavibacter, Curtobacterium, Rhodococcus, Erwinia, Xanthomonas, Ralstonia, and Agrobacterium, which are responsible for plant or cultivated mushroom diseases worldwide. In general, a lower activity was observed against bacteria belonging to the genus Pseudomonas. These results suggest the potential use of the above essential oils for the control of bacterial diseases.
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                Author and article information

                Journal
                bjps
                Brazilian Journal of Pharmaceutical Sciences
                Braz. J. Pharm. Sci.
                Universidade de São Paulo, Faculdade de Ciências Farmacêuticas (São Paulo, SP, Brazil )
                2175-9790
                2017
                : 53
                : 4
                : e00076
                Affiliations
                [4] orgnameUniversidade Federal da Paraíba orgdiv1Health Sciences Center orgdiv2Departament of Pharmaceutical Sciences Brazil
                [2] Araraquara São Paulo orgnameUniversidade Estadual Paulista orgdiv1School of Pharmaceutical Sciences orgdiv2Laboratory of Biotechnology Brazil
                [3] Araraquara São Paulo orgnameUniversidade Estadual Paulista orgdiv1School of Pharmaceutical Sciences orgdiv2Laboratory of Cell Biology Brazil
                [1] Araraquara São Paulo orgnameUniversidade Estadual Paulista orgdiv1School of Pharmaceutical Sciences orgdiv2Laboratory of Pharmacognosy Brazil
                Article
                S1984-82502017000400602 S1984-8250(17)05300400602
                10.1590/s2175-97902017000400076
                2df04991-12ab-4b9d-bc18-cc7a27ecce00

                This work is licensed under a Creative Commons Attribution 4.0 International License.

                History
                : 27 September 2016
                : 19 April 2017
                Page count
                Figures: 0, Tables: 0, Equations: 0, References: 37, Pages: 0
                Product

                SciELO Brazil

                Categories
                Article

                Carvone/antimicrobial activity,Carvone/chemoprevention,Carvone /cytotoxicity,Carvone/antifungal activity

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