Mayker Lazaro Dantas Miranda

Sesquiterpenos de Ocotea lancifolia (Lauraceae)

Six new eremophilane sesquiterpenes, (rel)-4β,5β,7β-eremophil-9-en-12-oic acid (1), (rel)-4β,5β,7β-eremophil-1(10)-en-12-oic acid (2), (rel)-4β,5β,7β-eremophil-1(10)-en-2-oxo-12-oic acid (3), (rel)-4β,5β,7β-eremophil-9-en-12,8α-olide (4), (rel)-4β,5β,7β-eremophil-9-en-12,8β-olide (5) and (rel)-4β,5β,7β-eremophil-9α,10α-epoxy-12-oic acid (6), were isolated from the leaves of a specimen of Ocotea lancifolia (Lauraceae). Two other known sesquiterpenes, 4β,5β,7β-eremophil-11-en- 10α-ol (7) reported for the first time in the genus Ocotea, and the aromadendrene sesquiterpene, spathulenol (8), were also isolated. Their structures were determined on the basis of spectral data (MS, IR, UV and NMR-1D and 2D) and subsequent comparisons with the literature.

Chemical Composition and Biological Activities of the Essential Oils from the Fresh Leaves of Citrus limonia Osbeck and Citrus latifolia Tanaka (Rutaceae)

This study aimed at determining, for the first time, the chemical composition of the essential oils from fresh leaves of Citrus limonia and Citrus latifolia and evaluating its in vitro antibacterial, trypanocidal, leishmanicidal and cytotoxic effects. The essential oils from fresh leaves of C. latifolia and C. limonia were extracted by hydro distillation and analyzed by GC-MS. The oil yield was 0.8% for C. latifolia and 0.5% for C. limonia, whereas 17 and 18 chemical components were identified for C. latifolia and for C. limonia, respectively. Major components were limonene (46.3 %), nerol (10.0 %) and 1,8-cineole (13.4 %). In vitro antibacterial activity was evaluated against the bacteria Streptococcus mitis, Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus and Bacteroides fragilis by the broth dilution method. Protozoa of the Trypanosomatidae family cause neglected tropical diseases, such as trypanosomiasis, whose treatment has depended on few available drugs. Therefore, the essential oils from fresh leaves of C. limonia and C. latifolia were also evaluated against the Y strain of Trypanosoma cruzi trypomastigotes, resulting in IC50 = 88.2 μg/mL and 51.7 μg/mL, respectively. Regarding the evaluation of the cytotoxic activity against fibroblasts LLCMK2 line, the essential oil from C. limonia (CC50 = 422.9 μg/mL) and C. latifolia (CC50 = 502.9 μg/mL) showed moderate cytotoxicity. The leishmanicidal activity of the essential oils from fresh leaves of C. limonia and C. latifolia were evaluated against promastigote forms of Leishmania amazonensis, resulting in IC50 = 2.63 μg/mL and 2.03 μg/mL, respectively. Thus, the essential oils from fresh leaves of Citrus limonia and Citrus latifolia had moderate antibacterial and trypanocidal activities and significant leishmanicidal activity.

Sesquiterpenos e outros constituintes das folhas de Pterodon pubescens Benth (Leguminosae)

In addition to β-sitosterol, stigmasterol, phaeophitin A, luteolin, kaempferol, quercetin, (+)-catechin, quercetin-3-O-α-L-rhamnopyranoside, rutin, and p-hydroxy-benzoic acid, six known sesquiterpenes, namely (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane, oplopanone, 1β,6α-dihydroxy-4(15)-eudesmene, caryophyllene oxide, α-cadinol, and spathulenol, were isolated from the leaves of Pterodon pubescens (Leguminosae) growing in the Cerrado of Mato Grosso do Sul, Brazil. The (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane corresponds to the correct structure of homalomenol D. The sesquiterpene oplopanone, which bears a modified cadinane skeleton, is being reported for the first time in this genus. The structures of the compounds were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparison with data reported in the literature.

Constituintes químicos das folhas de Riedeliella graciliflora Harms (Leguminosae)

A new salicylic acid derivative, pentacosanyl salicylate, was isolated from the leaves of the plant toxic to cattle, Riedeliella graciliflora, in addition to a digalactosyldiacylglycerol (DGDG), 1,2-di-O-α-linolenoyl-3-O-α-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-glycerol, kaempferol-3-O-β-D-glucopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, quercetin-3-O-α-L-rhamnopyranoside, rutin, (+)-catechin and the dimer (+)-catechin-(4β-8)-catechin, glutinol, squalene, β-sitosterol, stigmasterol, phytol, β-carotene, α-tocopherol and ficaprenol-12. Their structures were determined using spectral techniques (MS, IR, and NMR-1D and 2D) and based on literature data.

ÓLEO ESSENCIAL DAS FLORES DE Eugenia klotzschiana (MYRTACEAE): SUA COMPOSIÇÃO QUÍMICA E ATIVIDADES TRIPANOCIDA E CITOTÓXICA IN VITRO

A Doenca de Chagas e causada pelo Trypanosoma cruzi e os medicamentos mais utilizados em seu tratamento sao o nifurtimox e benzonidazol, que causam varios efeitos colaterais. O uso de produtos naturais no tratamento de doencas aumentou nos ultimos anos e as plantas tornaram-se uma alternativa promissora para o desenvolvimento de novos medicamentos. Portanto, este estudo teve como objetivo determinar a composicao quimica do oleo essencial das flores in natura de Eugenia klotzchiana e avaliar pela primeira vez seus potenciais tripanocida e citotoxico in vitro . O oleo essencial das flores in natura foi obtido por hidrodestilacao em aparato Clevenger e sua composicao quimica foi determinada por CG-EM. Os principais compostos encontrados no oleo essencial das flores foram: ?-cariofileno (21,1 %), biciclogermacreno (10,2 %) e espatulenol (20,9 %). Os resultados mostraram que o oleo essencial apresentou promissora atividade tripanocida contra formas tripomastigotas de Trypanosoma cruzi (IC 50 = 20,2 ?g/mL) e moderada citotoxicidade sobre fibroblastos na faixa de concentracao analisada (CC 50 = 250,5 ?g/mL). Em suma, o oleo essencial das flores in natura de Eugenia klotzchiana pode ser considerado uma excelente fonte de compostos bioativos para o desenvolvimento de novos medicamentos antiparasitarios. Palavras-chave: Eugenia klotzchiana , Myrtaceae, oleo essencial, flores, Trypanosoma cruzi , cytotoxic analysis.

In vitro antiparasitic activity and chemical composition of the essential oil from Protium ovatum leaves (Burceraceae)

Leishmaniasis and trypanosomiasis are globally widespread parasitic diseases which have been responsible for high mortality rates. Since drugs available for their treatment are highly hepatotoxic, nephrotoxic and cardiotoxic, adherence to therapy has been affected. Thus, the search for new, more effective and safer drugs for the treatment of these diseases is necessary. Natural products have stood out as an alternative to searching for new bioactive molecules with therapeutic potential. In this study, the chemical composition and antiparasitic activity of the essential oil from Protium ovatum leaves against trypomastigote forms of Trypanosoma cruzi and the promastigote forms of Leishmania amazonensis were evaluated. The essential oil was promising against trypomastigote forms of T. cruzi (IC50= 28.55 μg.mL-1) and L. amazonensis promastigotes (IC50 = 2.28 μg.mL-1). Eighteen chemical constituents were identified by Gas Chromatography coupled to Mass Spectrometry (GC-MS) in the essential oil, whose major constituents were spathulenol (17.6 %), caryophyllene oxide (16.4 %), β-caryophyllene (14.0 %) and myrcene (8.4 %). In addition, the essential oil from P. ovatum leaves had moderate cytotoxicity against LLCMK2 adherent epithelial cell at the concentration range under analysis (CC50 = 150.9 μg.mL-1). It should be highlighted that this is the first report of the chemical composition and anti-Trypanosoma cruzi and anti-Leishmania amazonensis activities of the essential oil from Protium ovatum leaves.

Chemical composition, anti-Trypanosoma cruzi and cytotoxic activities of the essential oil from green fruits of Protium ovatum (BURSERACEAE)

1MSc, Instituto Federal Goiano, Rio verde-GO, Brazil. E-mail: elisangelaborges49@hotmail.com 2PhD, Instituto Federal Goiano, Rio verde-GO, Brazil. E-mail: cassiacefetrv@gmail.com 3PhD, Universidade de Franca, Franca-SP, Brazil. E-mail: viviane.sampaio@unifran.edu.br 4PhD, Instituto Federal do Sudeste de Minas Gerais. Barbacena-MG, Brazil. E-mail: criscazal@yahoo.com.br 5MSc, Instituto Federal do Mato Grosso do Sul, Coxim-MS, Brazil. E-mail: allex_fonseca@yahoo.com.br 6 PhD, Instituto Federal do Sul de Minas Gerais, Pouso Alegre-MG, Brazil. E-mail: mayker.miranda@ifsuldeminas.edu.br Abstract Chagas disease is a major neglected tropical disease caused by Trypanosoma cruzi. It has been treated with the antiparasitic drugs nifurtimox and benzonidazole, which cause several side effects. The market for natural products has considerably grown lately and the use of plants has become an alternative to the development of novel drugs to cure the disease. Therefore, this study aimed at describing the chemical analysis of the essential oil from green fruits of Protium ovatum and evaluating their trypanocidal and cytotoxic potential. The essential oil was obtained by Clevenger hydrodistillation whereas its chemical composition was determined by gas chromatography coupled to mass spectrometry (GC-MS). The major compounds found in the essential oil from green fruits of P. ovatum were β-myrcene (62.0 %), α-pinene (11.3 %) and limonene (7.3 %). To the best of our knowledge, this was the first time that the chemical composition of the essential oil from green fruits of P. ovatum was described. Results showed that the essential oil had strong trypanocidal activity against trypomastigote forms of theY strain of Trypanosoma cruzi (IC50 = 1.2 μg/mL). In addition, the essential oil from green fruits of P. ovatum did not display cytotoxicity against LLCMK2 adherent epithelial cell at the concentration range under analysis (CC50 = 550.3 μg/mL). As a result, it is an excellent option for the development of novel antiparasitic drugs.

Chemical composition and in vitro antibacterial and antiproliferative activities of the essential oil from the leaves of Psidium myrtoides O. Berg (Myrtaceae)

Abstract In this study, the chemical composition and antibacterial and antiproliferative potential of the essential oil obtained from fresh leaves of Psidium myrtoides (PM-EO) against oral pathogens and human tumour cell lines were investigated for the first time. GC-FID and GC-MS analyses showed that trans-β-caryophyllene (30.9%), α-humulene (15.9%), α-copaene (7.8%), caryophyllene oxide (7.3%) and α-bisabolol (5.3%) are the major constituents of PM-EO. The antibacterial activity of PM-EO against a panel of oral pathogens was investigated in terms of their minimal inhibitory concentrations (MIC) using the broth microdilution method. PM-EO displayed moderate activity against Streptococcus mitis (MIC = 100 μg/mL), S. sanguinis (MIC = 100 μg/mL), S. sobrinus (MIC = 250 μg/mL), and S. salivarius (MIC = 250 μg/mL), and strong activity against S. mutans (MIC = 62.5 μg/mL). The antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumour cell lines (MCF-7, HeLa, and M059 J) was performed using the XTT assay. PM-EO showed 50% inhibition of normal cell growth at 359.8 ± 6.3 μg/mL. Antiproliferative activity was observed against human tumour cell lines, with IC50 values significantly lower than that obtained for the normal cell line, demonstrating IC50 values for MCF-7 cells (254.5 ± 1.6 μg/mL), HeLa cells (324.2 ± 41.4 μg/mL) and M059 J cells (289.3 ± 10.9 μg/mL). Therefore, the cytotoxicity of PM-EO had little influence on the antibacterial effect, since it showed antibacterial activity at lower concentrations. Our results suggest that PM-EO is a promising source of new antibacterial and antitumour agents.

Chemical composition and antibacterial activity of essential oils from Citrus aurantifolia leaves and fruit peel against oral pathogenic bacteria

Tooth decay is a major public health problem which affects a large number of people in several countries. Even though more than 700 bacterial species have been detected in the oral cavity, Streptococcus and Lactobacillus stand out as the genera that cause tooth decay and other periodontal diseases. In this study, essential oils from Citrus aurantifolia leaves (CL-EO) and fruit peel (CP-EO) were obtained by hydrodistillation by a Clevenger-type apparatus whereas their chemical composition was analyzed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Limonene (77.5 %), linalool (20.1 %), citronellal (14.5 %) and citronellol (14.2 %) were the main constituents found in the essential oils from C. aurantifolia leaves and fruit peel. Antibacterial activity of essential oils was evaluated in terms of its minimum inhibitory concentration (MIC) values by the broth microdilution method in 96-well microplates. Both CL-EO and CP-EO displayed some activity against all oral pathogens under investigation; MIC values ranged from 20 to 200 µg/mL. CL-EO and CP-EO not only had promising activity against Streptococcus mutans (MIC = 20 µg/mL) and Lactobacillus casei (31.25 µg/mL), but also displayed antibacterial activity against all studied cariogenic bacteria. Efficacy of essential oils against S. mutans and L. casei is noteworthy and should be further investigated.

Chemical composition and evaluation of antileishmanial and cytotoxic activities of the essential oil from leaves of Cryptocarya aschersoniana Mez. (Lauraceae Juss.)

Leishmaniasis is an endemic disease caused by protozoa of the genus Leishmania, which affects around two million people worldwide. One major drawback in the treatment of leishmaniasis is the emergence of resistance to current chemotherapeutics. Medicinal and aromatic plants constitute a major source of natural organic compounds. In this study, the leaf essential oil of Cryptocarya aschersoniana was obtained by hydrodistillation in a Clevenger-type apparatus, and the chemical composition was analyzed by GC-MS and GC-FID. The essential oil of these species was predominantly constituted by monoterpene hydrocarbons (48.8%). Limonene (42.3%), linalool (9.7%) and nerolidol (8.6%) were the main constituents in the oil of C. aschersoniana. The in vitro activity of the oil was evaluated against the promastigote forms of Leishmania amazonensis, the causative agent of cutaneous leishmaniasis in humans. The essential oil of C. aschersoniana showed high activity against L. amazonensis promastigote forms (IC50 = 4.46 µg/mL), however, it also demonstrated a relatively high cytotoxicity on mouse peritoneal macrophages (CC50 = 7.71 µg/mL). This is the first report of the chemical composition and the leishmanicidal and cytotoxic activities of the leaf essential oil of C. aschersoniana.