Contribuição ao conhecimento químico de plantas do nordeste - Lippia sidoides Cham

Um novo na ftoquinoide identificado como 6-oxo-3, 4, 4a, 5 -tetrahidro-3-hiroxi-2, 2-dimetilnafto-1, 2-pirano (6) foi isolado dos extratos metanólicos do caule e das folhas de Lippia sidoides Cham.. Ao lado da nova quinona (6) foram isoladas e identificadas outras substâncias conhecidas, tais como: ácido vanílico, carvacrol, 6, 7-dimetoxi-4', 5-dihidroxiflavona, lapachenol e isocatalponol. Foram ainda identificados os seguintes ácidos graxos: palmitico estéarico, araquidico, behênico e lignocérico.

Larvicidal activity of the essential oil from Lippia sidoides cham. against Aedes aegypti linn

The aim of this work was to study the larvicidal activity of Lippia sidoides essential oil against Aedes aegypti larvae. The essential oil and its hydrolate (saturated solution of essential oil in water) were obtained by vapor extraction and their chemical composition determined by GL-chromatography coupled to mass spectroscopy. Bioassays were run with the essential oil, pure and diluted hydrolate and with their main constituents thymol and carvacrol. The results obtained showed that L. sidoides essential oil and its hydrolate have larvicidal action against the mosquito A. aegypti, causing an almost instantaneous mortality. Thymol, an alkylated phenol derivative and one of the major components of L. sidoides essential oil, was identified as the active principle responsible for the larvicidal action, causing 100% larval mortality at the lowest tested concentration of 0.017% (w/v). These results suggest that the essential oil of L. sidoides is promising as larvicide against A. aegypti and could be useful in the search of newer, more selective, and biodegradable larvicidal natural compounds to be used in official combat programs and at home.

Anatomia comparada do lenho em raiz e caule de Lippia salviifolia Cham. (Verbenaceae)

O presente trabalho vem contribuir com informações sobre a anatomia estrutural da madeira de raiz e caule de L. salviifolia Cham. (Verbenaceae). O estudo foi conduzido em área de cerrado, no Município de Pratânia, Estado de São Paulo (23º02'55,5" S e 48º31'26,1" W). Três espécimes de Lippia salviifolia foram coletados. Amostras do caule foram coletadas à altura do peito (AP), isto é, a 1,30 m do solo e as amostras de raiz foram coletadas de 30 a 40 cm da base do tronco. Houve variação qualitativa e quantitativa entre o lenho de raiz e de caule. As características quantitativas mais relevantes que diferenciam o lenho da raiz do de caule em L. salviifolia foram comprimento e freqüência de vasos, comprimento, diâmetro e espessura da parede das fibras e largura e altura de raios. Camadas de crescimento bem definidas foram observadas no lenho de caule e raiz. Placas de perfuração simples e múltiplas foram observadas nos elementos de vaso tanto no lenho de caule quanto no de raiz, entretanto placas radiadas foram encontradas apenas no lenho de raiz. Foram observadas fibras septadas e raios mais largos no lenho de raiz.

Antimicrobial activity of the essential oil from Lippia sidoides, carvacrol and thymol against oral pathogens

Dental caries and periodontal disease are associated with oral pathogens. Several plant derivatives have been evaluated with respect to their antimicrobial effects against such pathogenic microorganisms. Lippia sidoides Cham (Verbenaceae), popularly known as "Alecrim-pimenta" is a typical shrub commonly found in the Northeast of Brazil. Many plant species belonging to the genus Lippia yield very fragrant essential oils of potential economic value which are used by the industry for the commercial production of perfumes, creams, lotions, and deodorants. Since the leaves of L. sidoides are also extensively used in popular medicine for the treatment of skin wounds and cuts, the objective of the present study was to evaluate the composition and antimicrobial activity of L. sidoides essential oil. The essential oil was obtained by hydro-distillation and analyzed by GC-MS. Twelve compounds were characterized, having as major constituents thymol (56.7%) and carvacrol (16.7%). The antimicrobial activity of the oil and the major components was tested against cariogenic bacterial species of the genus Streptococcus as well as Candida albicans using the broth dilution and disk diffusion assays. The essential oil and its major components thymol and carvacrol exhibited potent antimicrobial activity against the organisms tested with minimum inhibitory concentrations ranging from 0.625 to 10.0 mg/mL. The most sensitive microorganisms were C. albicans and Streptococcus mutans. The essential oil of L. sidoides and its major components exert promising antimicrobial effects against oral pathogens and suggest its likely usefulness to combat oral microbial growth.

Ação e caracterização química de óleos essenciais no manejo da antracnose do maracujá

Objetivou-se avaliar dois métodos de inoculação de Colletotrichum gloeosporioides em maracujá, testar a patogenicidade de diferentes isolados, o efeito fungitóxico e a composição química dos óleos essenciais das espécies medicinais alecrim-pimenta (Lippia sidoides Cham.), capim-santo [Cymbopogon citratus (D. C.) Stapf.], alfavaca-cravo (Ocimum gratissimum L.), no controle da antracnose [Colletotrichum gloeosporioides (Penz.)], associado ao estádio de maturação de frutos de maracujazeiro-amarelo. Avaliaram-se três experimentos, onde se testou a patogenicidade de seis isolados do fungo em delineamento inteiramente casualizado, com seis repetições, outro com o mesmo delineamento em esquema fatorial 2x2 (suspensão de conídios e disco de micélio) e frutos (verdes e maduros), com seis repetições. No tratamento com frutos, utilizou-se o delineamento inteiramente casualizado, em esquema fatorial 5x3+1, sendo cinco concentrações (0; 2; 4; 6 e 8µL mL-1) e três espécies medicinais, mais o tebuconazol, com cinco repetições. Fez-se a caracterização química dos óleos por cromatografia gasosa, com espectrometria de massas. Todos os isolados foram patogênicos. Os frutos maduros apresentaram maior diâmetro das lesões, quando inoculados com suspensão de conídios. O óleo de C. citratus proporcionou o menor diâmetro das lesões nos frutos, até a concentração de 6 µL mL-1. Na concentração de 8 µL mL-1, todos os óleos inibiram o desenvolvimento do fungo. O timol (30,24%), o citral (77,74%) e o eugenol (92,89%) foram componentes majoritários em L. sidoides, C. citratus e O. gratissimum, respectivamente.

In vitro antifungal activities of leaf extracts of Lippia alba (Verbenaceae) against clinically important yeast species

Introduction There are few studies reporting the antifungal activities of Lippia alba extracts. Methods A broth microdilution assay was used to evaluate the antifungal effects of Lippia alba extracts against seven yeast species of Candida and Cryptococcus. The butanol fraction was investigated by gas chromatography-mass spectrometry. Results The butanol fraction showed the highest activity against Candida glabrata. The fraction also acted synergistically with itraconazole and fluconazole against C. glabrata. The dominant compounds in the butanol fraction were 2,2,5-trimethyl-3,4-hexanedione, 3,5-dimethyl-4-octanone and hexadecane. Conclusions The butanol fraction may be a good candidate in the search for new drugs from natural products with antifungal activity.

Citral and carvone chemotypes from the essential oils of Colombian Lippia alba (Mill.) N.E. Brown: composition, cytotoxicity and antifungal activity

Two essential oils of Lippia alba (Mill.) N.E. Brown (Verbenacea), the carvone and citral chemotypes and 15 of their compounds were evaluated to determine cytotoxicity and antifungal activity. Cytotoxicity assays for both the citral and carvone chemotypes were carried out with tetrazolium-dye, which showed a dose-dependent cytotoxic effect against HeLa cells. Interestingly, this effect on the evaluated cells (HeLa and the non-tumoural cell line, Vero) was lower than that of commercial citral alone. Commercial citral showed the highest cytotoxic activity on HeLa cells. The antifungal activity was evaluated against Candida parapsilosis, Candida krusei, Aspergillus flavus and Aspergillus fumigatus strains following the standard protocols, Antifungal Susceptibility Testing Subcommittee of the European Committee on Antibiotic Susceptibility Testing and CLSI M38-A. Results demonstrated that the most active essential oil was the citral chemotype, with geometric means-minimal inhibitory concentration (GM-MIC) values of 78.7 and 270.8 μg/mL for A. fumigatus and C. krusei, respectively. Commercial citral showed an antifungal activity similar to that of the citral chemotype (GM-MIC values of 62.5 μg/mL for A. fumigatus and 39.7 μg/mL for C. krusei). Although the citronellal and geraniol were found in lower concentrations in the citral chemotype, they had significant antifungal activity, with GM-MIC values of 49.6 μg/mL for C. krusei and 176.8 μg/mL for A. fumigatus.

Chemical composition and antiprotozoal activities of Colombian Lippia spp essential oils and their major components

The chemical composition and biological activities of 19 essential oils and seven of their major components were tested against free and intracellular forms of Leishmania chagasi and Trypanosoma cruzi parasites as well as Vero and THP-1 mammalian cell lines. The essential oils were obtained from different species of Lippia, a widely distributed genus of Colombian plants. They were extracted by microwave radiation-assisted hydro-distillation and characterised by GC-FID and GC-MS. The major components were geranial, neral, limonene, nerol, carvacrol, p-cymene, γ-terpinene, carvone and thymol. The essential oil of Lippia alba exhibited the highest activity against T. cruzi epimastigotes and intracellular amastigotes with an IC50 of 5.5 μg/mL and 12.2 μg/mL, respectively. The essential oil of Lippia origanoides had an IC50 of 4.4 μg/mL in L. chagasi promastigotes and exhibited no toxicity in mammalian cells. Thymol (IC50 3.2 ± 0.4 μg/mL) and S-carvone (IC50 6.1 ± 2.2 μg/mL), two of the major components of the active essential oils, were active on intracellular amastigotes of T. cruziinfected Vero cells, with a selective index greater than 10. None of the essential oils or major components tested in this study was active on amastigotes of L. chagasi infected THP-1 cells.

Virucidal activity of Colombian Lippia essential oils on dengue virus replication in vitro

The inhibitory effect of Lippia alba and Lippia citriodora essential oils on dengue virus serotypes replication in vitro was investigated. The cytotoxicity (CC50) was evaluated by the MTT assay and the mode of viral inhibitory effect was investigated with a plaque reduction assay. The virus was treated with the essential oil for 2 h at 37ºC before cell adsorption and experiments were conducted to evaluate inhibition of untreated-virus replication in the presence of oil. Antiviral activity was defined as the concentration of essential oil that caused 50% reduction of the virus plaque number (IC50). L. alba oil resulted in less cytotoxicity than L. citriodora oil (CC50: 139.5 vs. 57.6 μg/mL). Virus plaque reduction for all four dengue serotypes was observed by treatment of the virus before adsorption on cell. The IC50 values for L. alba oil were between 0.4-32.6 μg/mL and between 1.9-33.7 μg/mL for L. citriodora oil. No viral inhibitory effect was observed by addition of the essential oil after virus adsorption. The inhibitory effect of the essential oil seems to cause direct virus inactivation before adsorption on host cell.

Influência da temperatura do ar de secagem sobre o teor e a composição química do óleo essencial de Lippia alba (Mill) N. E. Brown

Leaves of Lippia alba were submitted to six different drying treatments, using air at ambient temperature and heated up to 80 °C. The essential oil was extracted by steam distillation and analyzed by GC-MS. For the dried leaves, the oil content was reduced by 12 to 17% when compared with the fresh plant (0.66%). The major oil component was citral, representing 76% for the fresh plant, and varying from 82 to 84% for the dried material. These results showed that L. alba can be submitted to a drying process of up to 80 ºC without degradation and/or loss of the major, [LC1] active component.

Constituintes químicos e avaliação do potencial antiinflamatório e antioxidante de extratos das folhas de Chomelia obtusa Cham. & Schltdl. (Rubiaceae)

The phytochemical investigation of Chomelia obtusa leaves led to the isolation of four triterpenes (3-O-β-D-quinovopyranosyl-28-O-β-D-glycopyranosyl quinovic acid, 3-O-β-D-quinovopyranosyl-28-O-β-D-glycopyranosyl cincholic acid, and a mixture of ursolic and oleanolic acids), two flavonoids (3-O-β-D-glycopyranosyl quercetin, 3-O-[α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside] quercetin), besides bornesitol and a mixture of 3,5- and 4,5-O-dicaffeoyl quinic acids. The structures of the isolated compounds were assigned on the basis of spectroscopic data, including two-dimensional NMR methods. The anti-inflammatory and antioxidant activities of the crude methanolic extract and of its fractions were evaluated. This is the first report on the chemical and biological investigation of the Chomelia genus.

Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

The essential oil of the leaves of Lippia alba chemotype linalool-1,8-cineol was extracted by hidrodistillation at different seasons and analyzed by GC/MS. Qualitative and quantitative variations in regard to the period of harvesting have been performed and the results were correlated with meteorological data. The essential oil yield varied from 0.33 to 0.67%. The chemical diversity of the constituents increased throughout the year, being 1,8-cineol and linalool the major components. Possible biosynthetic routes of mono and sesquiterpenoids present in the essential oil are discussed.

Flavonoides e outras substâncias de Lippia sidoides e suas atividades antioxidantes

The chemical investigation of the ethanol extracts of stems, roots and leaves of Lippia sidoides led to the isolation of: steroid β-sitosterol, naphthoquinone tecomaquinone, monoterpene carvacrol, flavonoid 4',5,7-trihydroxyflavanone (naringenin), 3',4',5,7-tetrahydroxyflavanone and 4',5,7-trihydroxy-6-methoxyflavone flavonoids mixture, and 3,4,4',6'-tetrahydroxydihydrochalcone-2'-O-β-D-glucopyranoside and 4,4',6'-trihydroxydihydrochalcone-2'-O- β-D-glucopyranoside dihydrochalcones mixture. Their structures were characterized on the basis of spectral data, mainly ¹H and 13C NMR (1D and 2D) and mass spectra. The ethanol extract and isolated compounds were evaluated for their antioxidative properties using the method of inhibition of free radical DPPH (2,2-diphenyl-1-picrylhydrazyl).

Análise e discriminação de quimiotipos de Lippia graveolens H.B.K. da Guatemala por microextração em fase sólida, CG-EM e análise multivariada

SPME-GC-MS, PCA and HCA multivariate techniques were used in order to evaluate their applicability to discriminate the three chemotypes (thymol, carvacrol and mixed) described for L. graveolens of Guatemala. The leaves of L. graveolens are used for treatment of colds, bronchitis, and as seasoning for food preparations, yielding essential oil up to 4.34 %. Leaves of 35 individuals from eight populations, and eight composite samples were analyzed using a DVB/Carboxen/PDMS fiber and GC-MS. PCA and HCA were carried out using eight markers (p-cymene, cis-sabinene hydrate, linalool, terpinen-4-ol, thymol, carvacrol, (E)-caryophyllene and caryophyllene oxide). The three chemotypes of L. graveolens were satisfactorily discriminated.

Caracterização de chás de genótipos de Lippia gracilis schauer através de perfil cromatográfico por CLAE-DAD combinado com análises quimiométricas

In order to evaluate the effects of environmental factors on the content of secondary metabolites, the chemical profiles of infusions from leaves of seven genotypes of Lippia gracilis Schauer, sourced from two locations (Sergipe and Bahia state) and collected during different seasons: summer (with and without irrigation) and winter, were determined by HPLC-DAD. The fingerprint chromatograms were analyzed by PCA to evaluate similarities and differences among the samples. Results revealed differences among genotypes collected and cultivated under the same conditions, suggesting that three genotypes have greater resistance to drought conditions.