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Bol. latinoam. Caribe plantas med. aromát ; 23(3): 437-447, mayo 2024. tab
Article in Spanish | LILACS | ID: biblio-1538171


The aim of this study was to optimize by response surface design, the extraction of the leaf essential oil (EO) from Minthostachys mollis [HBK] Griseb., grown in Ecuador, using steam distillation. The factors used were extraction time (XTIE) of 60, 105 and 150 min and plant material/water ratio (XRMA) of 1:3, 1:4 and 1:5. The optimal combination was reached with XRMA 1:5 and XTIE 150 min, obtaining a process yield of 0.67%. The chemical composition of the EO analyzed by GC - MS was determined, where the main compounds were carvacryl acetate (44.01%), carvacrol (16.51%) and menthone (8.20%). The anti oxidant capacity of EO was evaluated using the FRAP and ABTS methodologies, with an IC 50 243.21 µmol Fe 2+ /g and 0.12 mg/mL, respectively. In addition, the antimicrobial activity of EO was found against Pseudomonas aeruginosa , Salmonella enterica , Escherich ia coli and Staphylococcus aureus .

El objetivo del estudio fue optimizar, mediante un diseño de superficie respuesta, la extracción d el aceite esencial (AE) de hojas de Minthostachys mollis [HBK] Griseb. del Ecuador, mediante destilación por arrastre de vapor. Los factores fueron el tiempo de extracción (XTIE) de 60, 105 y 150 min, y relación de material vegetal/ agua destilada (XRMA) d e 1:3, 1:4 y 1:5. La combinación óptima se logró con XTIE 150 min y XRMA 1:5 para un rendimiento de 0,67%. Se determinó la composición química del AE por GC - MS donde los compuestos mayoritarios fueron acetato de carvacrilo (44,01%), carvacrol (16,51%) y me ntona (8,20%). Se evaluó la capacidad antioxidante del AE por las metodologías FRAP y ABTS, con CI 50 de 243,21 µmol Fe 2+ /g y 0,12 mg/mL, respectivamente. Además, se demostró la actividad antimicrobiana contra Pseudomonas aeruginosa , Salmonella enterica , Es cherichia coli y Staphylococcus aureus .

Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Anti-Infective Agents/chemistry , Plant Leaves/chemistry , Lamiaceae/metabolism , Lamiaceae/chemistry , Ecuador
Bol. latinoam. Caribe plantas med. aromát ; 22(6): 864-878, nov. 2023. tab, graf
Article in English | LILACS | ID: biblio-1554462


Triterpenes are very important secondary metabolites with wide structural diversity and significant role in pharmacy and medicine. In the present research, a comparative study of pharamacological activities of the triterpene fractions obtained from several plant species belonging to Lamiaceae family, was carried out. In - vitro anti - proliferative activity was performed using a standard proliferation assay based on tetrazolium salts. In vitro anti - inflammatory activity of triterpene fractions was determined by an assay of inhibition of albumin denaturation. In general, the triterpene fractions obtained from plant species belonging to Lam iaceae family showed a strong anti - proliferative activity and anti - inflammatory activity. The triterpene fraction of Rosmarini folium showed the strongest anti - proliferative activity (GI 50 range from 4 to 37 µg/ml) and the strongest anti - inflammatory activ ity in the range from 57.27% to 80.69%. This comparative study provides scientific evidence to support the traditional use of Lamiacae plant species for medical purposes as anti - inflammatory and anti - proliferative medicines.

Los triterpenos son metabolitos secundarios muy importantes, con una amplia diversidad estructural y un rol significativo en la farmacia y la medicina. En esta investiga ción, se realizó un estudio comparativo de las actividades farmacológicas de las fracciones de triterpenos obtenidas de varias especies de plantas pertenecientes a la familia Lamiaceae. La actividad antiproliferativa in vitro se realizó mediante un ensayo estándar de proliferación basado en sales de tetrazolio. Se determinó la actividad antinflamatoria de las fracciones de triterpeno s mediante un ensayo de inhibición de desnaturalización de la albúmina. En general, las fracciones de triterpeno s obtenidas de las plantas pertenecientes a la familia Lamiaceae mostraron una actividad antiproliferativa y antinflamatoria fuerte. La fracción de triterpeno de Folium Rosmarini mostró la actividad antiproliferativa más fuerte (rango GI 50 entre 4 y 37 µg/m L ) y la más f uerte actividad antinflamatoria en el rango de 57,27% a 80,69%. Este estudio comparativo provée evidencia científica para apoyar el uso tradicional de especies de plantas Lamiaceae para usos médicos como medicinas antinflamatorios y antiproliferativas.

Triterpenes/pharmacology , Plant Extracts/pharmacology , Lamiaceae/chemistry , Triterpenes/chemistry , Lamiaceae/metabolism , Anti-Inflammatory Agents
Bol. latinoam. Caribe plantas med. aromát ; 22(2): 255-267, mar. 2023. tab, ilus
Article in English | LILACS | ID: biblio-1555677


Food spoilage is a widely neglected problem and the constant use of synthetic fungicides could develop resistant fungi. The objective of this study was to evaluate the chemical composition and antimicrobial activity of Tetradenia riparialeaf essential oil against foodborne disease microorganisms. Leaf essential oil was obtained by hydrodistillation and identified by gas chromatography coupled to mass spectrometry. The antimicrobial activity was studied by broth microdilution. The major compounds identified were oxygenated sesquiterpenes (43.6%): 14-hydroxy-9-epi-(E)-cariophylene (20.8%) and τ-cadinol (18.4%); followed by oxygenated diterpenes (24.6%): 6,7-dehydroroyleanone (12.6%) and 9ß, 13ß-epoxy-7-abiethene (10.6%); sesquiterpenic hydrocarbons (17.1%) and oxygenated monoterpenes (7.4%): fenchone (5.6%). The essential oil had broad antibacterial and antifungal activity, mainly against A. versicolor and P. ochrochloron with fungistatic and fungicidal activities and B. cereus, L. monocytogenes, and S. aureuswith bacteriostatic and bactericidal activities. T. riparialeaf essential oil is a potential alternative to control microorganisms-

El deterioro de los alimentos es un problema ampliamente desatendido y el uso constante de fungicidas sintéticos podría desarrollar hongos resistentes. El objetivo de este estudio fue evaluar la composición química y la actividad antimicrobiana del aceite esencial de hoja de Tetradenia riparia contra microorganismos patógenos transmitidos por los alimentos. El aceite esencial de hoja se obtuvo por hidrodestilación y se identificó mediante cromatografía de gases acoplada a espectrometría de masas. La actividad antimicrobiana estudiada fue por microdilución en caldo. Los compuestos principales del aceite esencial se identificaron como sesquiterpenos oxigenados (43,6%): 14-hidroxi-9-epi-(E)-cariofileno (20,8%) y τ-cadinol (18,4%); seguido de diterpenos oxigenados (24,6%): 6-7-deshidroroileanona (12,6%) y 9ß, 13ß-epoxi-7-abieteno (10,6%); hidrocarburos sesquiterpénicos (17,1%) y monoterpenos oxigenados (7,4%): fenchona (5,6%). Tenía amplia actividad antibacteriana y antifúngica, principalmente contra A. versicolor y P. ochrochloron con actividades fungistáticas y fungicidas, y principalmente contra B. cereus, L. monocytogenes y S. aureus con actividades bacteriostáticas y bactericidas. El aceite esencial de hoja de T. riparia es una alternativa potencial para controlar microorganismos.

Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Lamiaceae/chemistry , Anti-Infective Agents/therapeutic use
Chinese Journal of Natural Medicines (English Ed.) ; (6): 927-937, 2023.
Article in English | WPRIM | ID: wpr-1011004


Six new abietane diterpenoids (1-6) and five undescribed iridoids (7-11) have been isolated from the aerial parts of Caryopteris mongolica. The intricate structural characterization of these compounds was meticulously undertaken using an array of advanced spectroscopic techniques. This process was further enhanced by the application of DP4+ probability analyses and electronic circular dichroism (ECD) calculations. Following isolation and structural elucidation, the cytotoxicity of these compounds was evaluated. Among them, compound 3 stood out, displaying significant cytotoxic activity against HeLa cells with an IC50 value of 7.83 ± 1.28 μmol·L-1. Additionally, compounds 1, 2, 4, 9, and 10 manifested moderate cytotoxic effects on specific cell lines, with IC50 values ranging from 11.7 to 20.9 μmol·L-1.

Humans , Abietanes/chemistry , HeLa Cells , Lamiaceae/chemistry , Circular Dichroism , Diterpenes/chemistry , Molecular Structure
Biosci. j. (Online) ; 39: e39026, 2023.
Article in English | LILACS | ID: biblio-1425189


Tetradenia riparia (Hochst.) Codd (Lamiaceae) is a shrub, commonly known as ginger bush or false myrrh, and several studies have shown that T. riparia exhibits a variety of biological properties. This study aimed to determine the chemical composition of T. riparia essential oil and its fractions, investigate their anticholinesterase activity, and assess their larvicidal activity against the cattle tick Rhipicephalus microplus and the mosquito Aedes aegypti. Eleven essential oil fractions were obtained by fractionation and analyzed by gas chromatography/mass spectrometry. Larvicidal activity against R. microplus and third-instar A. aegypti was assessed using a larval packet test and a larval immersion test, respectively. Anticholinesterase activity was determined by a bioautographic method. Forty-nine compounds were identified in the essential oil, of which the major classes were oxygenated sesquiterpenes (45.95%) and sesquiterpene hydrocarbons (35.20%) and the major components were isospathulenol (17.40%), ß-caryophyllene (15.61%), 14-hydroxy-9-epi-caryophyllene (10.07%), 14-hydroxy-α-muurolene (8.32%), and 9ß,13ß-epoxy-7-abietene (5.53%). Bioassays showed that T. riparia essential oil (LC50 = 1.56 µg/mL) and FR3 (LC50 = 0.30 µg/mL) were the most active against R. microplus and A. aegypti larvae, respectively. The essential oil and FR1, FR2, and FR3 exhibited acetylcholinesterase inhibitory activity. These results indicate that T. riparia essential oil and its fractions hold promise in the development of novel, environmentally safe agents for the control of R. microplus and A. aegypti larvae.

Ticks , Aedes , Lamiaceae/toxicity , Lamiaceae/chemistry , Larvicides
Bol. latinoam. Caribe plantas med. aromát ; 21(4): 446-454, jul. 2022. tab, graf
Article in English | LILACS | ID: biblio-1526668


Aromatic and medicinal plants are of great importance to determine the contents of the active compounds of plant origin and to evaluate them depending on variety and climate factors in order to determine the phenolic, antioxidant enzyme activity, vitamin contents in species belonging to the Lamiaceae family. Examination of the characteristics of different species, the highest peroxidase (POD) enzyme activity, ascorbate peroxidase (AxPOD), total antioxidant (TA), malondialdehyte (MDA), caffeic acids (CA), vitamin C contents,and chloric acid (ChA) were obtained in the M. longifoliaspecies. The highest vitamin E and catalase (CAT) were determined in the S. hortensisspecies but the highest total phenolic (TP), superoxide dismutase (SOD) enzyme, hydrogen peroxide (H2O2) and chlorogenic acid (ChgA) were determined in the S. spicigeraspecies. As a result of PCA analysis, it can be said that Mentha longifolia(L.) Hudson and Satureja spicigeraspecies have significant value in terms of biochemical and phenolic content.

Las plantas aromáticas y medicinales son de gran importancia para determinar el contenido de los compuestos activos de origen vegetal y evaluarlos en función de la variedad y factores climáticos con el fin de determinar la actividad enzimática fenólica, antioxidante, contenido vitamínico en especies pertenecientes a la familia Lamiaceae. El examen de las características de diferentes especies, la mayor actividad enzimática de peroxidasa (POD), ascorbato peroxidasa (AxPOD), antioxidante total (TA), malondialdehído (MDA), ácidos cafeicos (CA), contenido de vitamina C y ácido clorhídrico (ChA) se obtuvieron en la especie M. longifolia. La mayor cantidad de vitamina E y catalasa (CAT) se determinó en la especie S. hortensis, pero la mayor cantidad total de enzima fenólica (TP), superóxido dismutasa (SOD), peróxido de hidrógeno (H2O2) y ácido clorogénico (ChgA) se determinó en la especie S. spicigera. Como resultado del análisis de PCA, se puede decir que las especies Mentha longifolia(L.) Hudson y Satureja spicigeratienen un valor significativo en términos de contenido bioquímico y fenólico.

Plants, Medicinal/chemistry , Lamiaceae/chemistry , Phenols/analysis , Vitamins/analysis , Principal Component Analysis , Antioxidants/analysis
Braz. J. Pharm. Sci. (Online) ; 58: e19233, 2022. tab, graf
Article in English | LILACS | ID: biblio-1374569


Abstract In the present study, the metabolite profiling of methanolic extract from aerial parts of Satureja khuzistanica Jamzad, as an endemic medicinal plant from Iran, was evaluated using HPLC-PDA-ESI. Then, the main compound from the extract was isolated and purified by using extensive chromatographic techniques. In addition, the structure of the isolated compounds was elucidated using 1D, 2D NMR, and MS spectrometry, upon which 22 compounds were identified. The antibacterial activity of diosmetin 7-rutinoside (6) and linarin (13) in combination with carvacrol as a major compound of the essential oil was tested against Pseudomonas aeruginosa and Staphylococcus aureus through disc diffusion and minimum inhibitory concentration methods. The results indicated that the linarin, when mixed with carvacrol as the main compounds in the essential oil of the plant, has a satisfactory activity against both Pseudomonas aeruginosa and Staphylococcus aureus with MIC values of 0.16 and 0.18 µg/mL, respectively. Further, the fractional inhibitory concentration (FIC) index indicated that this compound had synergism with carvacrol.

Plants, Medicinal/anatomy & histology , Oils, Volatile/analysis , Lamiaceae/chemistry , Satureja/classification , Pseudomonas aeruginosa/isolation & purification , Spectrum Analysis/instrumentation , Microbial Sensitivity Tests/instrumentation , Chromatography, High Pressure Liquid/methods
Bol. latinoam. Caribe plantas med. aromát ; 19(2): 149-160, mar. 2020. ilus, tab
Article in English | LILACS | ID: biblio-1104061


Clinopodium mexicanum (Benth.) Govaerts (Lamiaceae) is a native plant of Mexico. This plant is used in traditional Mexican medicine for the treatment of cultural specific syndromes such as "susto", "nervios" or "espanto", conditions related to anxiety and depression. In addition, it has a high biocultural value for its medicinal and culinary use and for its exchange value in various indigenous areas of México. This review aims to compile updated information about the ethnobotanical, phytochemistry and commercialization aspects of Clinopodium mexicanum, and it focuses on the potential use of this species as a raw material in the phytopharmaceutical industry for the treatment of anxiety and pain. Moreover, it would be a viable productive alternative for many rural communities, which could not only produce the raw material but who could also add value to the sale of the plant.

Clinopodium mexicanum (Benth.) Govaerts, es una planta nativa de México. Es usada en la medicina tradicional mexicana para tratar síndromes de filiación cultural como "susto", "nervios" o "espanto", los cuales están asociados a la ansiedad y depresión. Además, la planta presenta un alto valor biocultural por sus usos: medicinal, culinario y por el valor de cambio que tiene en áreas indígenas de México. La revisión presentada tiene como objetivo compilar información actualizada sobre aspectos etnobotánicos, fitoquímicos y comercialización de Clinopodium mexicanum. Igualmente señalar el potencial uso de esta especie como materia prima para la elaboración de productos para la ansiedad y el dolor por parte de la industria fitofarmacéutica. Además de ser una alternativa productiva para muchas comunidades rurales, las cuales pueden venderla como materia prima o como producto derivado.

Plants, Medicinal , Ethnobotany , Lamiaceae/chemistry , Medicine, Traditional , Commerce , Phytochemicals/analysis , Indigenous Peoples , Mexico
China Journal of Chinese Materia Medica ; (24): 1357-1362, 2020.
Article in Chinese | WPRIM | ID: wpr-1008579


The aim of this paper was to evaluate the key production processes of Schizonepetae Herba formula granules based on the new model of combining characteristic chromatogram with quantitative transfer relationship. The rationality of production process design was evaluated by studying the intermediates in different processes of formula granules, analyzing the loss of index component pulegone in each step, and establishing the characteristic chromatogram. The content of pulegone in 10 batches of standard decoction ranged between 0.067% and 0.124%(70%-130% of the average value), and the transfer rate of pulegone was 44.58%-93.97%. After the improvement of the production process, the content of pulegone in Schizonepetae Herba formula granules was 0.093%, and the transfer rate of pulegone was 68.38%, which was consistent with the parameters range of standard decoction. This study emphasized the integrality of the research process of traditional Chinese medicine(TCM) formula granules, and provided a new idea for the quality control of TCM with content determination as the main evaluation index for a long time.

Chromatography, High Pressure Liquid , Drugs, Chinese Herbal/chemistry , Lamiaceae/chemistry , Medicine, Chinese Traditional , Quality Control
Braz. j. biol ; 79(1): 87-99, Jan.-Mar 2019. tab, graf
Article in English | LILACS | ID: biblio-983999


Abstract This study aimed to carry out an ethnobotanical survey of medicinal plants used by inhabitants of the Rodeadouro Island, Jatoba Island and Massangano Island, located in The Submedium São Francisco River Valley. Also phytochemicals and preliminary pharmacological tests were performed to species most cited by the community. Ethnobotanical data were collected through observation visits and semi-structured interviews with 12 key informants. We calculated the relative importance (RI), the percentage of agreement related to the main uses (cAMU) and use value (UV). The aerial parts of Rhaphiodon echinus (Ness & Mart.) Schauer were used to obtain the lyophilizate (LYO-Re), crude ethanol extract (CEE-Re) and their hexanic (HEX-Re), chloroform (CLO-Re) and ethyl acetate (EA-Re) fractions. The microdilution technique was used for determining Minimum inhibitory concentration (MIC) for selected microorganisms. Already the spasmolytic effect was evaluated in isolated uterus fragments of Wistar rats, pre contracted with KCl 60 mM. We found 34 species cited, belonging to 22 families. The most plants were grown by locals. There were 51 different diseases, but the main indication was infectious and parasitic diseases. The species R. echinus was the most reported and it was indicated for urinary tract infection and dysmenorrhea. The screening revealed a higher prevalence of flavonoids, tannins, lignans and saponins in LYO-Re and AE-Re. Already terpene compounds were more present in HEX-Re and CLO-Re. The RE-Re fraction stood out with strong effect against E. coli and S. aureus while CEE-Re has moderate effect against gram-negative bacteria. The evaluation of the spasmolytic activity showed that LYO-Re, CEE-Re and HEX-Re fractions have similar activity, with partial effect and concentration-dependent response. This work brought about knowledge and use of medicinal plants by the riparian of the São Francisco River. It also revealed the importance of other methodologies for scientific evidence for the popular use of R. echinus.

Resumo Objetivou-se realizar um levantamento etnobotânico de plantas medicinais utilizadas nas ilhas do Massangano, Jatobá II e Rodeadouro, localizadas entre Petrolina-PE e Juazeiro-BA, no submédio do rio São Francisco e posterior investigação fitoquímica e farmacológica da espécie mais citada, conforme a indicação da comunidade. Realizaram-se visitas de observação nas ilhas e os dados etnobotânicos foram coletados por entrevistas semiestruturadas com 12 informantes-chave. Calculou-se a Importância Relativa (IR), a Porcentagem Corrigida de Concordância quanto ao Uso Principal (CUPc) e o Valor de Uso (VU). Utilizaram-se as partes aéreas da espécie mais citada para obtenção do extrato etanólico bruto (EEB-Re), suas frações hexânica (HEX-Re), clorofórmica (CLO-Re) e acetato de etila (AE-Re); o produto liofilizado (LIO-Re) e o óleo essencial (OE-Re). A técnica de microdiluição foi usada para determinar a Concentração Inibitória Mínima (CIM) para microorganismos selecionados. A atividade espasmolítica foi avaliada em fragmentos isolados de útero de ratas Wistar pré-contraídos com KCl 60 mM. Foram relatadas 34 espécies, contidas em 22 famílias diferentes. A maioria das plantas era cultivada pelos moradores. Registraram-se 51 enfermidades diferentes, mas a principal indicação foi doenças parasitárias e infecciosas. A espécie Rhaphiodon echinus (Ness & Mart.) Schauer foi a mais citada, com principal indicação para tratar infecção do trato urinário e dismenorreia. O screening fitoquímico revelou prevalência de flavonoides, taninos, lignanas e saponinas em LIO-Re e AE-Re e compostos terpênicos em HEX-Re e CLO-Re. Os testes antibacterianos mostraram que AE-Re é mais atuante contra E. coli e S. aureus do que para P. aeruginosa. O EEB-Re tem efeito parcial contra bactérias gram-negativas e OE-Re possui moderada resposta para todos microorganismos testados. LIO-Re, EEB-Re e HEX-Re possuem atividade espasmolítica dependente da concentração, sem diferença significativa e sem relaxamento total. Este trabalho trouxe conhecimento sobre o uso de plantas medicinais pelos ribeirinhos do rio São Francisco e revela a importância de estudos mais aprofundados para a comprovação científica do uso popular da R. echinus.

Animals , Female , Rats , Plants, Medicinal/chemistry , Bacteria/drug effects , Lamiaceae/chemistry , Medicine, Traditional , Uterus/drug effects , Brazil , Microbial Sensitivity Tests , Rats, Wistar , Ethnobotany
China Journal of Chinese Materia Medica ; (24): 5465-5472, 2019.
Article in Chinese | WPRIM | ID: wpr-1008422


The aim of this paper was to screen the active targets of Schizonepetae Herba and Saposhnikoviae Radix in the treatment of ulcerative colitis by means of network pharmacology,and to investigate their mechanism of action. The effective components of Schizonepetae Herba and Saposhnikoviae Radix were screened out by traditional Chinese medicine systematic pharmacological( TCMSP)database,with oral bioavilability( OB) ≥30% and drug-like( DL) ≥18% selected as the thresholds. Target PPI network was built between the main components and their corresponding targets. One hundred and eighty-two human genes corresponding to the medicine target sites were obtained from Uniprot database; 3 874 genes corresponding to ulcerative colitis were obtained from Genecard database.A total of 115 intersection genes were screened from disease genes and medicine genes,and the PPI interaction analysis was conducted by using String tool. Disease-target PPI network was drawn by using Cytoscape software,and component-target-disease network was constructed. One hundred and eight nodes and 1 882 connections were found,and then Cytoscape software was used to merge the networks and filter the core network for gene GO function analysis and KEGG pathway enrichment analysis. The mechanism of Schizonepetae Herba and Saposhnikoviae Radix was then verified by animal experiment. Gene GO functional analysis suggested that biological process,molecular functions and cell components were involved,and it was found that ulcerative colitis might be related to transcription factor activity,and cytokine receptor binding,etc. Gene KEGG pathway enrichment analysis showed that the mechanism of ulcerative colitis might be associated with TNF and Toll-like receptors( TLRs) signaling pathway-mediated cytoinflammatory factors interleukin-1( IL-1) and interleukin-6( IL6). The possible mechanism of the effective components of Schizonepetae Herba and Saposhnikoviae Radix in treating ulcerative colitis might be related to intervening the cytokine receptor binding of TNF and TLRs signaling pathways,reducing the transcription of nuclear factor-kappaB( NF-κB),and inhibiting the secretion of intestinal inflammatory factors IL-1 and IL-6.

Animals , Humans , Apiaceae/chemistry , Colitis, Ulcerative/drug therapy , Databases, Genetic , Drugs, Chinese Herbal/therapeutic use , Interleukins/metabolism , Lamiaceae/chemistry , Medicine, Chinese Traditional , Phytotherapy , Plant Roots/chemistry , Protein Interaction Mapping , Signal Transduction , Software , Toll-Like Receptors/metabolism
Rev. Soc. Bras. Med. Trop ; 51(3): 291-296, Apr.-June 2018. tab
Article in English | LILACS | ID: biblio-957425


Abstract INTRODUCTION: In the present study, we determined the chemical composition of Clinopodium macrostemum essential oil obtained by microwave-assisted hydrodistillation and its effect on the growth and development of Culex quinquefasciatus mosquito larvae. METHODS: The essential oil compounds were identified by gas chromatography-mass spectrometry analysis, and bioassays were conducted to evaluate the influence on the developmental stages of early second instar larvae of Cx. quinquefasciatus until the emergence of adults, using essential oil concentrations of 50, 100, 200, 400, and 800mg/L. RESULTS: The gas chromatography-mass spectrometry analyses revealed that the leaf essential oil of C. macrostemum contained 32 compounds and the major chemical compounds identified were linalool (55.4%), nerol (6.4%), caryophyllene (6.25%), menthone (5.8%), geraniol acetate (4.1%), terpineol (3.7%), and pulegone (2.8%). The essential oil yield obtained by microwave-assisted hydrodistillation was 0.8% at 20 min. The treatments showed lethal concentrations (LC50 and LC90) of 22.49 and 833.35mg/L, respectively, after the final measurement of the total number of dead larvae (second, third, and fourth instars), and LC50 and LC90 of 6.62 and 693.35mg/L, respectively, at the end of the experimental period. The essential oil inhibited the growth and development of the mosquito larvae by 32% (relative growth index = 0.68) at 50mg/L, and up to 47% (relative growth index = 0.53) at 800mg/L. CONCLUSION: The present study demonstrated the larvicidal effect of C. macrostemum essential oil on Cx. quinquefasciatus, which can be attributed to the oxygenate compounds obtained by the extraction method.

Animals , Oils, Volatile/pharmacology , Lamiaceae/chemistry , Culex/drug effects , Larva/drug effects , Biological Assay , Oils, Volatile/isolation & purification , Oils, Volatile/chemistry , Lamiaceae/classification , Culex/classification , Lethal Dose 50 , Gas Chromatography-Mass Spectrometry , Microwaves
An. acad. bras. ciênc ; 89(4): 2825-2832, Oct.-Dec. 2017. tab, graf
Article in English | LILACS | ID: biblio-886866


ABSTRACT Abnormal multiplication of oral bacteria causes dental caries and dental plaque. These diseases continue to be major public health concerns worldwide, mainly in developing countries. In this study, the chemical composition and antimicrobial activity of the essential oil of Vitex agnus-castus leaves (VAC‒EO) collected in the North of Brazil against a representative panel of cariogenic bacteria were investigated. The antimicrobial activity of VAC-EO was evaluated in terms of its minimum inhibitory concentration (MIC) values by using the broth microdilution method in 96-well microplates. The chemical constituents of VAC-EO were identified by gas chromatography (GC‒FID) and gas chromatography‒mass spectrometry (GC‒MS). VAC‒EO displayed some activity against all the investigated oral pathogens; MIC values ranged from 15.6 to 200 μg/mL. VAC-EO had promising activity against Streptococcus mutans (MIC= 15.6 μg/mL), Lactobacillus casei (MIC= 15.6 μg/mL), and Streptococcus mitis (MIC= 31.2 μg/mL). The compounds 1,8-cineole (23.8%), (E)-β-farnesene (14.6%), (E)-caryophyllene (12.5%), sabinene (11.4%), and α-terpinyl acetate (7.7%) were the major chemical constituents of VAC‒EO. VAC-EO displays antimicrobial activity against cariogenic bacteria. The efficacy of VAC-EO against S. mutans is noteworthy and should be further investigated.

Sesquiterpenes/pharmacology , Plant Extracts/pharmacology , Lamiaceae/chemistry , Vitex/chemistry , Dental Caries/drug therapy , Lacticaseibacillus casei/drug effects , Anti-Bacterial Agents/pharmacology , Plants, Medicinal , Sesquiterpenes/classification , Streptococcus mutans , Brazil , Oils, Volatile/isolation & purification , Oils, Volatile/pharmacology , Polycyclic Sesquiterpenes , Gas Chromatography-Mass Spectrometry , Anti-Bacterial Agents/isolation & purification
An. acad. bras. ciênc ; 89(3): 1369-1379, July-Sept. 2017. tab, graf
Article in English | LILACS | ID: biblio-886755


ABSTRACT Natural steroids and triterpenes such as b-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.

Humans , Triterpenes/pharmacology , Lamiaceae/chemistry , Pentacyclic Triterpenes/pharmacology , Fabaceae/chemistry , Antineoplastic Agents/pharmacology , Triterpenes/isolation & purification , Triterpenes/chemistry , Drug Screening Assays, Antitumor , Lamiaceae/classification , Inhibitory Concentration 50 , Cell Line, Tumor , Esters , Pentacyclic Triterpenes/isolation & purification , Pentacyclic Triterpenes/chemistry , Fabaceae/classification , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/chemistry
Braz. j. biol ; 76(1): 176-184, Feb. 2016. tab, graf
Article in English | LILACS | ID: lil-774516


Abstract This study was developed to evaluate the effect of seasonality on the yield and chemical composition of the essential oil (EO) of Hesperozygis ringens (Benth.) Epling, a native species from the Brazilian Pampa. Leaves were collected from four specimens of a single population in each of the four seasons for a year and were extracted in triplicate by hydro-distillation for 2 hours. The yield of EO (% w/w) was calculated on fresh weight basis (FWB), and the 16 oil samples were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used as statistical tools to evaluate differences in chemical composition. The highest yields were obtained in autumn, spring and summer (2.32-4.38%), while the lowest yields were detected in winter, ranging from 1.15 to 1.91%. Oxygenated monoterpenoids were the predominant class of chemical constituents in the EO obtained in all seasons, showing the highest contents in autumn and summer, and pulegone was identified as a major compound, whose contents varied between 54.13 and 81.17%. The EO samples were divided into three chemical groups by HCA and PCA and were assigned to the same group, except for the three samples gathered in winter. The results showed a seasonal influence on the yield and chemical composition of the EO.

Resumo Este estudo foi desenvolvido a fim de avaliar o efeito da sazonalidade no rendimento e composição química do óleo essencial (OE) de Hesperozygis ringens (Benth.) Epling., uma espécie nativa do Pampa brasileiro. Folhas foram coletadas de quatro indivíduos de uma mesma população, em cada uma das quatro estações de um ano, e foram extraídas em triplicada por hidrodestilação durante 2 horas. O rendimento do OE (% m/m) foi calculado considerando a base fresca (BF) e as 16 amostras de óleo foram analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e cromatografia gasosa com detector de ionização de chamas (CG-DIC). Análise Hierárquica de Cluster (AHC) e Análise de Componentes Principais (ACP) foram utilizadas como ferramentas estatísticas para avaliar as diferenças na composição química. Os maiores rendimentos foram obtidos no outono, primavera e verão (2,32-4,38%), enquanto que os menores foram detectados no inverno, variando de 1,15 até 1,91%. Os monoterpenoides oxigenados foram a classe predominante dos constituintes do OE obtido em todas as estações, apresentando os maiores teores no outono e no verão, e a pulegona foi identificada como o constituinte majoritário, cujos teores variaram entre 54,13 e 81,17%. As amostras de OE foram divididas em três grupos químicos por AHC e ACP e foram classificadas no mesmo grupo, com exceção de três amostras coletadas no inverno. Os resultados demonstraram influência sazonal no rendimento e na composição química dos OE.

Lamiaceae/chemistry , Lamiaceae/metabolism , Oils, Volatile/chemistry , Oils, Volatile/metabolism , Cluster Analysis , Flame Ionization , Gas Chromatography-Mass Spectrometry , Principal Component Analysis , Plant Leaves/chemistry , Seasons
Mem. Inst. Oswaldo Cruz ; 110(8): 1024-1034, Dec. 2015. tab, graf
Article in English | LILACS | ID: lil-769826


The herbaceous shrub Tetradenia riparia has been traditionally used to treat inflammatory and infectious diseases. Recently, a study showed that T. riparia essential oil (TrEO) obtained in summer has antileishmanial effects, although these results could be influenced by seasonal variation. This study evaluated the activity of the TrEO obtained in different seasons against Leishmania (Leishmania) amazonensis, in vitro and in vivo. The compounds in the TrEO were analysed by gas chromatography-mass spectrometry; terpenoids were present and oxygenated sesquiterpenes were the majority compounds (55.28%). The cytotoxicity and nitric oxide (NO) production were also tested after TrEO treatment. The TrEO from all seasons showed a 50% growth inhibitory concentration for promastigotes of about 15 ng/mL; at 30 ng/mL and 3 ng/mL, the TrEO reduced intracellular amastigote infection, independently of season. The TrEO from plants harvested in summer had the highest 50% cytotoxic concentration, 1,476 ng/mL for J774.A1 macrophages, and in spring (90.94 ng/mL) for murine macrophages. NO production did not change in samples of the TrEO from different seasons. The antileishmanial effect in vivo consisted of a reduction of the parasite load in the spleen. These results suggest that the TrEO has potential effects on L. (L.) amazonensis, consonant with its traditional use to treat parasitic diseases.

Animals , Female , Antiprotozoal Agents/pharmacology , Lamiaceae/chemistry , Leishmania/drug effects , Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Antiprotozoal Agents/isolation & purification , Cytotoxins/pharmacology , Gas Chromatography-Mass Spectrometry , Growth Inhibitors/pharmacology , In Vitro Techniques , Leishmania/classification , Lymph Nodes/parasitology , Mice, Inbred BALB C , Macrophages, Peritoneal/drug effects , Macrophages, Peritoneal/parasitology , Nitric Oxide/analysis , Oils, Volatile/chemistry , Parasite Load , Plant Extracts/chemistry , Plant Leaves/chemistry , Seasons , Sesquiterpenes/analysis , Spleen/parasitology , Time Factors
Braz. j. microbiol ; 46(2): 519-525, Apr-Jun/2015. tab, graf
Article in English | LILACS | ID: lil-749743


In Brazilian folk medicine, Tetradenia riparia (Hochst.) Codd. (Lamiaceae) is used to treat toothaches and dental abscesses and diseases induced by worms, bacteria, or fungi. This paper aims to investigate the chemical composition and the antibacterial effects of the essential oil obtained from Tetradenia riparia leaves (TR-EO) grown in Southeastern Brazil against a representative panel of oral pathogens. We evaluated the antibacterial activity of TR-EO in terms of the minimal inhibitory concentration (MIC). We identified aromadendrene oxide (14.0%), (E,E)-farnesol (13.6%), dronabinol (12.5%), and fenchone (6.2%) as the major constituents of TR-EO. TR-EO displayed MIC values between 31.2 and 500 μg/mL, with the lowest MIC value being obtained against Streptococcus mitis (31.2 μg/mL), S. mutans (62.5 μg/mL), S. sobrinus (31.2 μg/mL), and Lactobacillus casei (62.5 μg/mL). In time-kill experiments, TR-EO demonstrated bactericidal activity against S. mutans within the first 12 h, resulting in a curve profile similar to that of chlorhexidine. These results revealed that the essential oil of Tetradenia riparia displays promising activity against most of the selected cariogenic bacteria, including Streptococcus mutans.

Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Lacticaseibacillus casei/drug effects , Lamiaceae/chemistry , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Streptococcus/drug effects , Anti-Bacterial Agents/isolation & purification , Brazil , Microbial Sensitivity Tests , Oils, Volatile/isolation & purification
Braz. j. microbiol ; 45(4): 1341-1347, Oct.-Dec. 2014. graf, tab
Article in English | LILACS | ID: lil-741285


Bacterial infections cause thousands of deaths in the world every year. In most cases, infections are more serious because the patient is already weakened, and often, the bacteria are already resistant to the antibiotics used. Counterparting this negative scenario, the interest in medicinal plants as an alternative to the synthetic antimicrobial drugs is blossoming worldwide. In the present work, we identified the volatile compounds of ethanol extracts of Melissa officinalis, Mentha sp., Ocimum basilicum, Plectranthus barbatus, and Rosmarinus officinalis by gas chromatography/mass spectrometry (GC/MS). Also was evaluated antimicrobial activity of ethanol extracts against 6 bacteria of clinical interest, and was tested the interaction of these extracts with a commercial antibiotic streptomycin. Phytol was a compound identified in all extracts by GC/MS, being majoritary component in Plectranthus barbatus and Rosmarinus officinalis. The Gram-positive bacteria were more sensitive to ethanol extracts, and Plectranthus barbatus and Rosmarinus officinalis were the most active extracts. Ethanol extracts exhibited a synergetic effect with streptomycin. These results encourage additional studies, in order to evaluate the possibilities of using ethanol extracts of Lamiaceae family as natural source for antibacterial activity.

Humans , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Drug Synergism , Lamiaceae/chemistry , Plant Extracts/pharmacology , Streptomycin/pharmacology , Volatile Organic Compounds/pharmacology , Anti-Bacterial Agents/isolation & purification , Gas Chromatography-Mass Spectrometry , Microbial Sensitivity Tests , Plant Extracts/isolation & purification , Volatile Organic Compounds/isolation & purification
Bol. latinoam. Caribe plantas med. aromát ; 13(3): 254-269, mayo 2014. ilus, tab
Article in Spanish | LILACS | ID: lil-768854


This work presents the analysis by GC-MS of volatile metabolites of six Lamiaceae from Arauca (Colombia). In stems and leaves of Eriope crassipes were determined as the most abundants: citronellic acid (53,8 percent and 66,2 percent), and methyl citronellate (15,7 percent and 14,5 percent). In the inflorescences of Hyptis conferta were identified: t-cadinol (49,4 percent), and caryophyllene oxide (13,0 percent). From leaves and flowers of Hyptis dilatata were found: delta-3-carene (11,0 percent and 0,5 por ciento), camphor (43,8 percent and 12,2 percent), bornyl acetate (3,2 percent and 25,5 percent), E-caryophyllene (12,8 percent and 22,3 percent), and palustrol (6,0 percent and 10,3 percent). In the leaves of Hyptis brachiata were recognized: E-caryophyllene (8,3 percent), alpha-humulene (19,8 percent), and germacrene D (13,0 percent). The principal compounds in leaves and flowers of Hyptis suaveolens were: alpha-phellandrene (9,4 percent and 0,4 percent), limonene (10,5 percent and 2,5 percent), 1,8-cineole (1,3 percent and 15,2 por ciento), fenchone (10,8 por ciento and tr), E-caryophyllene (26,3 por ciento and 8,0 por ciento), and germacrene D (6,7 por ciento and 14,0 por ciento). In the leaves of Hyptis mutabilis were determined: sabinene (6,6 percent) beta-elemene (6,8 percent), germacrene D (14,9 percent), beta-selinene (8,8 percent), alpha-selinene (9,1 percent), and bicyclogermacrene (6,1 percent), as the most abundants.

Este trabajo presenta el análisis por GC-MS de los metabolitos volátiles de seis Lamiaceae recolectadas en Arauca (Colombia). En tallos y hojas de Eriope crassipes se determinaron como mayoritarios: ácido citronélico (53,8 por ciento y 66,2 por ciento), y citronelato de metilo (15,7 por ciento y 14,5 por ciento). En las inflorescencias de Hyptis conferta se identificaron: t-cadinol (49,4 por ciento), y óxido de cariofileno (13,0 por ciento). En hojas y flores de Hyptis dilatata se encontraron: delta-3-careno (11,0 por ciento y 0,5 por ciento), alcanfor (43,8 por ciento y 12,2 por ciento), acetato de bornilo (3,2 por ciento y 25,5 por ciento), E-cariofileno (12,8 por ciento y 22,3 por ciento), y palustrol (6,0 por ciento y 10,3 por ciento). En las hojas de Hyptis brachiata se reconocieron: E-cariofileno (8,3 por ciento), alfa-humuleno (19,8 por ciento), y germacreno D (13,0 por ciento). Los compuestos principales en hojas y flores de Hyptis suaveolens fueron: alfa-felandreno (9,4 por ciento y 0,4 por ciento), limoneno (10,5 por ciento y 2,5 por ciento), 1,8-cineol (1,3 por ciento y 15,2 por ciento), fenchona (10,8 por ciento y tr), E-cariofileno (26,3 por ciento y 8,0 por ciento), y germacreno D (6,7 por ciento y 14,0 por ciento). En las hojas de Hyptis mutabilis se determinaron: sabineno (6,6 por ciento), beta-elemeno (6,8 por ciento), germacreno D (14,9 por ciento), beta-selineno (8,8 por ciento), alfa-selineno (9,1 por ciento), y biciclogermacreno (6,1 por ciento), como los más abundantes.

Oils, Volatile/chemistry , Plant Leaves/chemistry , Lamiaceae/chemistry , Camphor/analysis , Camphanes/analysis , Caprylates/analysis , Distillation , Gas Chromatography-Mass Spectrometry , Sesquiterpenes/analysis
Bol. latinoam. Caribe plantas med. aromát ; 13(3): 285-296, mayo 2014. ilus, tab, graf
Article in English | LILACS | ID: lil-768855


In the present work an analytical methodology to micro scale based on the use of the HS-SPME/GC-MS to determine volatile compounds present in Clinopodium odorum (Griseb.) Harley (Lamiaceae)was optimized and settled differences and similarities with itsessential oil. A systematic description of the volatile components of flowers, stems, leaves and combined aerial parts (whole plant) was constructed via GC-MS analyses of HS-SPME adsorbed compounds and of essential oils obtained through hydrodistillation of the same tissues. Pulegone was the main component of both the HS-SPME analysis and essential oil analysis. In addition, piperitenone oxide andpiperitone oxide were the other main components in the essential oil whereas in the HS-SPME analysis cis-isopulegone and menthone prevailed. The HS-SPME method can achieve comparable results to those obtained by essential oil analysis, by using very fewer samples, ashorter extraction time and a much simpler procedure.

En el presente trabajo se ha optimizado una metodología analítica a micro-escala basada en HS-SPME/GC-MS para determinar los compuestos volátiles presentes en Clinopodium odorum (Griseb.) Harley (Lamiaceae), y se establecieron diferencias y similitudes con su aceite esencial. Se realizó una descripción sistemática de los componentes volátiles de flores, tallos, hojas y partes aéreas combinadas(planta entera) a partir de los análisis por GC-MS a través del sistema HS-SPME y de los aceites esenciales. Pulegona fue el componenteprincipal tanto del análisis por HS-SPME, como del aceite esencial. Además, el óxido de piperitenona y el óxido de piperitona eran los otroscomponentes principales en el aceite esencial mientras que en el análisis por HS-SPME, prevalecieron cis-isopulegona y mentona. El método de HS-SPME puede lograr resultados comparables a los obtenidos por el análisis de aceite esencial, mediante el uso de muestras de menor tamaño, un tiempo de extracción más corto y un procedimiento más simple.

Oils, Volatile/chemistry , Gas Chromatography-Mass Spectrometry/methods , Distillation , Lamiaceae/chemistry , Menthol/analysis , Monoterpenes/analysis