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Interest in the study of bioactive molecules present in plant organs such as root, leaves, stems or flowers, has increased significantly in search of applications in fields such as medicine and agriculture, mainly due to the bactericidal, antifungal and insecticides properties found in different plant species. In this study, leaf and bark extracts obtained at reduced pressure of Z. caribaeum were evaluated for their antibacterial and antifungal activity using the Kirby-Bauer agar disk diffusion technique. We found that extracts from the bark of this tree show a greater biological activity compared to extracts obtained from leaf, mainly against Grampositive bacteria such as S. aureus and S. mutans. However, there was no significant biological activity against gram-negative bacteria such as E. coli or Morganella sp. The composition of the extract determined by gas chromatography coupled to mass spectrophotometry (GC-MS), reveal the presence of the compound 3.5-dihydroxy-6-methyl-2.3-dihydro-4H-piran-one (32.8%) as a majority compound, which has been reported with antibacterial properties. The biological activity of the extracts of Z. caribeaum represents a potential source for the development of drugs for the control of microbial diseases.

En el presente trabajo se aislaron tres compuestos puros, Cantin-6-ona (A01), dihidrosanguinarina (A03) y dihidrogliciteína (A04), dos alcaloides con m/z=221.0729, m/z=341.1091, y el isoflavonoide con masa m/z=287.0939 respectivamente, se identificaron mediante técnicas de UHPLC acoplado a espectrometría de masas y para cantin-6-ona se corroboro la estructura mediante RMN protónica. Además se identificaron 40 compuestos del extracto etanólico de corteza entre los que se destacan: 3,4-dimetilcatinona, (R, Z)-alfa-bisaboleno, 2- feniletil beta-D-glucopiranosido, 6-piperazin-1-il-Isoquinolina y 29 compuestos de extracto acuoso de hoja, estos son algunos 1-(2,3-dihidro-6-metil-1H-pirrolizin-5-il)- 1,4-pentanediona, N-(3-oxododecanoil)homoserina lactona, Ciclopirox, 9- Nitroantraceno, Isofenoxazina, Dietiltoluamida, Granisetron, Sesquicineol, Oleoil sarcosina, Tridodecilamina. Los subextractos de hojas en bencina de petróleo y diclorometano, presentaron la mejor actividad antioxidante por el método ABTS+•, con valores de IC50 136,2 ppm y 41,15 ppm respectivamente, este último también mostró actividad antioxidante frente al radical DPPH• con IC50 72,5 ppm, así como también el subextracto en acetato de etilo de corteza que presentó un valor IC50 de 70,45 ppm, mientras que por el método de Potencial Antioxidante de Reducción Férrica (FRAP) a todas las concentraciones evaluadas los extractos que presentaron poder de reducción del Fe+3 a Fe+2 fueron los subextractos en diclorometano hojas y bencénico de la corteza. El extracto acuoso de hojas presento mayor actividad inhibitoria de crecimiento expresada en porcentaje de reducción de crecimiento fúngico, con IC50 entre 900 y 1200 mg/mL, C90 y IC99 con valores entre 1000 y 2100 mg/mL. TABLA DE CONTENIDO 1. INTRODUCCIÓN ................................................18 2. OBJETIVOS...........................................20 2.1 OBJETIVO GENERAL................................................20 2.2 OBJETIVOS ESPECIFICO........................................20 3. MARCO TEÓRICO...............................................21 3.1 Generalidades de la familia Rutáceas.........................................21 3.2 Características morfológicas del género Zanthoxylum...............21 3.3 Distribución mundial del género Zanthoxylum....................22 4. SECCIÓN EXPERIMENTAL..............................................38 4.1 MATERIAL VEGETAL:......................................38 4.2 MATERIALES, REACTIVOS Y EQUIPOS...........................39 4.2.1. Materiales y reactivos.............................................39 4.2.2 Equipos........................................................39 4.3 TRATAMIENTO DE LA MUESTRA................................................40 4.3.1 Tratamiento del material vegetal.........................................40 4.4 Aislamiento y purificación de componentes químicos de Zanthoxylum caribaeum......................40 4.4.1 Preparación de la muestra para análisis cromatográficos.........................41 4.5 EVALUACIÓN DE LA ACTIVIDAD ANTIOXIDANTE...................................41 4.5.2 Protocolo del ensayo DPPH●.........................43 5. ENSAYOS DE LA ACTIVIDAD ANTIMICROBIANA...................................44 6. ANÁLISIS CROMATOGRÁFICOS.......................................45 6.1 Condiciones cromatográficas.................................45 6.1.2 Espectrometría de masas.....................................45 6.1.3 Software..........................................46 6.1.4 Extracción de características moleculares...............................................46 7. RESULTADOS Y ANÁLISIS....................................48 7.1 Marcha fitoquímica...............................48 7.1.1 Imágenes del resultado.....................................48 7.1.2 CCD del extracto etanólico de las hojas de Z. caribaeum......................................49 7.1.3 Extracto etanólico de hojas de Z. caribaeum..................................50 7.2 Análisis de los metabolitos del extracto de corteza Zanthoxylum caribaeum utilizando la base de datos METLIN..........60 7.3 Evidencia espectros energía Media MS-FINDER..........................72 7.4 EVALUACIÓN DE LA ACTIVIDAD ANTIOXIDANTE......................................92 7.4.1 Evaluación de actividad antioxidante por el Método DPPH•.................................92 7.4.2 Evaluación de actividad antioxidante por el método ABTS+•..............................101 7.4.3 EVALUACIÓN DE ACTIVIDAD ANTIOXIDANTE POR EL MÉTODO FRAP.......................110 8 RESULTADOS DE LA ACTIVIDAD ANTIMICROBIANA..................................112 9. CONCLUSIÓN..............................................116 10. BIBLIOGRAFÍA...........................................................117 Maestría Magíster en Ciencias Químicas Trabajos de Investigación y/o Extensión

The pollen morphology of 13 native taxa of the Rutaceae from Argentina was studied under optical and scanning electron microscopy to provide new data that would allow delimiting these taxa. The species considered were Balfourodendron riedelianum, Esenbeckia densiflora, E. febrifuga, E grandiflora, Helietta apiculata, Pilocarpus pennatifolius, Zanthoxylum caribaeum, Z. coco, Z. fagara, Z. petiolare, Z. rhoifolium, Z. riedelianum and Zanthoxylum rigidum ssp. hasslerianum. The general morphological characteristics of the pollen grain of these species are: radiosymmetric, isopolar; small, medium or large size; 3-colporate or 4-colporate; colpus with costa colpi; semitectate (reticulate, striate reticulate or striate). Sculpture, shape and size are the main characters that allow differentiating the studied taxa. Morphological characters among the species are discussed and a species key is presented.

Rutaceae species, especially of the genus Zanthoxylum L., are known for possessing a well-diversified chemical composition with high potential for pharmacological activity. A variety of Zanthoxylum species are distributed throughout Brazil. This study aimed to characterize the leaf anatomy and identify the histochemical composition of the secretory material from the secretory structures of Z. caribaeum leaves. Leaves of Z. caribaeum were collected and processed for anatomical, histochemical and micromorphological characterization following standard methodologies. The leaves have an unstratified epidermis and glandular trichomes in epidermal depressions on the abaxial surface. Extrafloral nectaries were also observed on the abaxial surface. The leaf is hypostomatic and the stomata are anomocytic. The mesophyll is dorsiventral and has secretory cavities. The mesophyll cavities produce a secretion of lipidic nature and the cavities on the leaf margin produce a secretion of mixed nature, with neutral lipids and essences. In summary, our findings show that the leaves of Z. caribaeum have secretory structures like glandular trichomes that can function as extrafloral nectaries and cavities. The characterization of the leaf anatomy of Z. caribaeum can provide relevant data for future taxonomic studies of the genus.

ilustraciones, fotografías, gráficas, tablas La Enfermedad de Alzheimer (EA) es la demencia más común, un desorden neurodegenerativo de carácter multifactorial caracterizado por la presencia de placas amiloides, ovillos neurofibrilares, reducción de la actividad colinesterasa, estrés oxidativo, entre otros mecanismos. A pesar de la inversión en investigación durante las últimas décadas, se considera que la investigación debe tomar nuevos enfoques, buscar nuevas dianas biológicas y desarrollar nuevos fármacos, es por ello que en este trabajo se realiza la búsqueda y caracterización de compuestos con actividad multi-diana a partir de productos naturales, teniendo en cuenta que estudios previos de los grupos de investigación demostraron la actividad biológica y el potencial neuroprotector de especies de la familia Rutaceae y particularmente las pertenecientes al género Zanthoxylum de la flora colombiana, las cuales poseen efectos antioxidantes, agonista de LXR e inhibidores de colinesterasas. El objetivo de este trabajo fue realizar una búsqueda de agentes neuroprotectores a partir de la especie Z. caribaeum. Inicialmente se obtuvo un extracto mediante maceración etanólica en frio de la raíz, posteriormente se determinaron el tipo de metabolitos presentes usando técnicas de coloración, se fraccionó el extracto usando cromatografía liquida al vacío (CLV), los compuestos se purificaron usando técnicas cromatográficas, se identificó la estructura química de los compuestos mediante técnicas espectroscópicas y espectrométricas, se evaluó la capacidad antioxidante mediante el método DPPH, y protección del foto-blanqueo del β-caroteno, se evaluó la actividad inhibitoria de acetil y butiril colinestearasas mediante el método Ellman, se realizaron ensayos de viabilidad celular y neuro-protección por MTT, se evaluó la actividad agonista de LXR mediante el ensayo del gen reportero y se determinó la capacidad antiagregante de Aβ de los compuestos mediante un modelo in vitro de cinética de agregación del péptido amiloide. Dentro de los resultados, se logró determinar en el extracto la presencia de metabolitos de tipo alcaloidal, fenólicos, aminas, entre otros. Tanto el extracto como algunas fracciones obtenidas, presentaron actividad agonista de LXR, actividad captadora de radicales libres, protección frente a la peroxidación lipídica y actividad inhibitoria de la butiril colinesterasa; de estas fracciones y mediante el aislamiento químico dirigido, se obtuvo el compuesto 10H-furano [3,2-a] carbazol, el compuesto 5,7 -dimetoxi-4H-cromen-4-ona, y una mezcla de esteroles que contiene estigmasterol y β-sitosterol. El compuesto 10H-furano [3,2-a] carbazol presentó actividad agonista de LXR, se observó efecto neuroprotector y actividad antiagregante de Aβ; el compuesto 5,7 -dimetoxi-4H-cromen-4-ona se reporta por primera vez en esta especie, presenta efecto neuroprotector y actividad antiagregante de Aβ; por su parte, la mezcla de esteroles estigmasterol y β-sitosterol presentó actividad agonista de LXR, efecto neuroprotector y actividad antiagregante de Aβ. Nuestros resultados nos permiten concluir que tanto las fracciones y compuestos aislados de Z. caribaeum presentan un potencial multifuncional para la terapéutica de la EA. (Texto tomado de la fuente). Alzheimer's Disease (AD) is the most common dementia, a multifactorial neurodegenerative disorder characterized by the accumulation of amyloid plaques, neurofibrillary tangles, reduced cholinesterase activity, oxidative stress, among other mechanisms. Despite the investment in research during the last decades, it is considered that research must take new approaches, search for new biological targets and develop new drugs. Here we carry out the search and characterization of compounds with multi-functional activity from Ethanolic extract of Z.caribaeum roots. Previous studies of our research groups demonstrated the biological activity and neuroprotective potential of species of the Rutaceae family and particularly those belonging to the Zanthoxylum genus, which have antioxidant effects, LXR agonist activity and cholinesterase inhibitors. The aim of this work was the search for neuroprotective agents from Zanthoxylum caribaeum. Ethanolic extract of Z.caribaeum roots, was obtained by maceration. The kind of metabolites presents in the extract were determined using coloration assays, the fractionation was carried out using vacuum liquid chromatography (VLC). The compounds were purified by chromatographic techniques, the chemical structures were identified by spectroscopic and spectrometric techniques. The multifunctional potential of ethanolic extract roots, and fractions was determined by antioxidant capacity (DPPH method, and protection from photo-bleaching of β-carotene), inhibitory activity of cholinesterases (acetyl and butyryl cholinesterases), and LXR agonist effect (the gene-reporter assay). In the extract was detected the presence of alkaloidal, phenolic, amines metabolites. The extract and some fractions have LXR agonist activity, free radical scavenging activity, protection against lipid peroxidation, and butyryl cholinesterase inhibitory activity. The compound 10H-furan[3,2-a]carbazole, 5,7-dimethoxy-4H-chromen-4-one, and a mixture of sterols containing stigmasterol and β-sitosterol were isolated and this multifuntional potential was determined by the LXR agonistic activity, Neuroprotective and the Aβ antiaggregating capacity in model in vitro of amyloid peptide aggregation kinetics The compound 10H-furan [3,2-a] carbazole showed LXR agonist activity, neuroprotective effect and antiaggregant activity of Aβ; the compound 5,7-dimethoxy-4H-chromen-4-one is reported for the first time in this species and has a neuroprotective effect and antiaggregant activity of Aβ. Stigmasterol and β-sitosterol presented LXR agonist activity, neuroprotective effect and Aβ antiaggregant activity. Our results allow us to conclude that both the fractions and compounds isolated from Z. caribaeum have multifunctional potential for therapeutics in AD. Maestría Magíster en Neurociencias Neurofarmacología

ilustraciones, fotografías a color, gráficas, tablas En el presente documento se presentan los resultados del estudio fitoquímico y de actividad biológica del extracto etanólico de raíz de Zanthoxylum caribaeum (Rutaceae) y la obtención de metabolitos secundarios con posible actividad neuroprotectora aplicable en el tratamiento de la enfermedad de Alzheimer. Para el estudio fitoquímico biodirigido se usaron métodos de extracción y purificación clásicos como la extracción liquido – liquido (usando solventes de polaridad creciente: hexano, acetato de etilo, butanol y agua), cromatografía en columna y seguimiento de pureza por cromatografía en capa delgada, mientras que los métodos de caracterización e identificación de metabolitos se aplicaron técnicas instrumentales como cromatografía liquida de alta eficiencia, espectrometría de masas y métodos espectroscópicos como la resonancia magnética nuclear de hidrogeno y carbono, en una y dos dimensiones. El estudio de actividad bilógica se planteó en dos etapas; la primera por bioatugrafía directa de seguimiento al proceso de extracción y purificación del extracto crudo, facciones y compuestos puros usando DPPH y -Caroteno para evaluar el potencial antioxidante y Acetilcolinesterasa para evaluar el potencial inhibitorio de la encima; de esta manera se pretendió orientar la purificación hacia la obtención de metabolitos secundarios con capacidad inhibitoria de la encima y/o actividad antioxidante o captadores de radicales libres ya que estas dos propiedades han sido asociadas a la pérdida de las capacidades cognitivas de las personas que padecen el síndrome de Alzheimer. Adicionalmente se incluyó el reactivo de Dragendorff, con el fin de establecer que fracciones contenían metabolitos tipo alcaloide, ya que se ha evidenciado que estas moléculas presentan actividad neuroprotectora. En la segunda etapa del estudio biológico permitió evaluó de forma cuantitativa la capacidad antioxidante y anticolinérgica de las fracciones principales procedentes de la partición con solventes y de los metabolitos aislados aplicando métodos colorimétricos en microdilución usando Fisostigmina como control positivo para la actividad acticolinergica y Quercetina para la actividad antioxidante; en los casos en los que fue posible, se calculó la IC50. Es así como la purificación bioguiada condujo al aislamiento y caracterización de los siguientes compuestos: 6,8-dimetoxi-2-H-1-quinolin-2-ona, 3-((1-metilciclopentil) amino) quinolin-2(1H)-ona, 104-ozaxol[3,2-a]quinolina y ácido antranilico y la evaluación de su posible actividad neuroprotectora, basada en los resultados de actividad antioxidante y anticolinérgica, demostró que los compuestos de manera individual presentan actividades antioxidantes medias a bajas y que la actividad anticolinérgica se pierde a medida que se avanza en la putificación, siendo más activas las fracciones que los compuestos puros. (Texto tomado de la fuente). The present document presents the results of the phytochemical and biological activity study of the ethanolic extract of the root of Zanthoxylum caribaeum (Rutaceae) and the obtaining of secondary metabolites with possible neuroprotective activity applicable in the treatment of Alzheimer's disease. For the bio-directed phytochemical study, classic extraction and purification methods were used such as liquid-liquid extraction (using solvents of increasing polarity: n-hexane, ethyl acetate, n-butanol and water), column chromatography and purity monitoring by thin layer chromatography. While the methods of characterization and identification of metabolites were applied instrumental techniques such as high efficiency liquid chromatography, mass spectrometry and spectroscopic methods such as nuclear magnetic resonance of hydrogen and carbon, in one and two dimensions. The study of biological activity was planned in two stages; the first by direct bioatugraphy of follow-up to the extraction and purification process of the crude extract, factions and pure compounds using DPPH and -Carotene to evaluate the antioxidant potential and Acetylcholinesterase to evaluate the inhibitory potential of the enzyme; In this way, it was intended to orient purification towards obtaining secondary metabolites with inhibitory capacity of the enzyme and / or antioxidant activity or free radical scavengers since these two properties have been associated with the loss of cognitive abilities of people who suffer from Alzheimer's syndrome. Additionally, the Dragendorff reagent was included, in order to establish which fractions contained alkaloid-like metabolites, since it has been shown that these molecules have neuroprotective activity. In the second stage of the biological study, it was possible to quantitatively evaluate the antioxidant and anticholinergic capacity of the main fractions from the partition with solvents and the isolated metabolites applying colorimetric methods in microdilution using Physostigmine as a positive control for acticholinergic activity and Quercetin for the antioxidant activity; In the cases where it was possible, the IC50 was calculated. Thus, the bioguided purification led to the isolation and characterization of the following compounds: 6,8-dimethoxy-2-H-1-quinolin-2-one, 3-((1-methylciclopentil) amino) quinolin-2(1H)-one, 104-ozaxol [3,2-a] quinoline and Anthranilic acid and the evaluation of its possible neuroprotective activity, based on the results of antioxidant and anticholinergic activity, showed that the compounds individually present medium to low antioxidant activities and that the anticholinergic activity is lost as the putification progresses, the fractions being more active than the pure compounds. Ministerio de Ciencias, Tecnología e Innovación Maestría Magíster en Ciencias - Química Productos Naturales

ilustraciones, gráficas La Enfermedad de Alzheimer (EA) es la principal causa de demencia en el mundo, se proyecta como el mayor problema de salud pública en el mundo para el año 2050. Su etiología es desconocida, se caracteriza por la pérdida progresiva de la memoria y patológicamente por la acumulación de péptidos beta-amiloide (Aβ) y la proteína Tau-hiperfosforilada. La hipótesis amiloide es la más aceptada, postula que el origen de la enfermedad comienza con la acumulación de Aβ, conlleva a procesos inflamatorios, desregulación de quinasas, incremento de especies reactivas de oxígeno, reducción de células madre neuronales, perdida de espinas dendríticas y muerte neuronal, explicando la demencia. Se ha evidenciado que la activación farmacológica de los receptores X hepáticos (LXR) en modelos animales de EA ha producido mejoría cognitiva asociada con incremento de expresión de las proteínas APOE y ABCA1, reducción de astrogliosis y microgliosis, protección de la plasticidad sináptica y espinas dendríticas. Los productos naturales vegetales han representado una fuente promisoria de moléculas bioactivas de características multimodales para el tratamiento de la EA, debido a sus altas cantidades de compuestos alcaloidales. Por su parte, Zanthoxylum caribaeum es una especie arbórea perteneciente a la familia Rutaceae que ha sido seleccionada luego de un amplio screening de plantas colombianas por su alto contenido de alcaloides, actividad agonista de LXRs, antiagregante de Aβ, antioxidante e inhibidora de acetilcolinesterasas in vitro. El objetivo de este trabajo fue de evaluar el efecto de un extracto etanolico de Zanthoxylum caribeum en un modelo in vivo de EA. Se realizó la administración oral a ratones triple-transgenicos de EA (3xTg-AD) y controles, encontrando mejoría de la memoria espacial en el laberinto acuático de Morris, incremento en la expresión de ABCA1 y ApoE, reducción del marcaje para marcadores moleculares de progresión de la EA. Adicionalmente, se observó un incremento en la expresión de proteínas asociadas con la función sináptica Sinapsina1, Shank 1/2/3 y PSD-95. En conclusión, se describió el efecto de un extracto etanólico crudo de Zanthoxylum caribaeum sobre los principales marcadores fisiopatológicos de la EA con potencial uso terapéutico en el modelo 3xTg-AD. (Texto tomado de la fuente). Alzheimer's disease (AD) is the main cause of dementia worldwide, it is projected as the largest public health problem in the world by the year 2050. Its etiology is unknown, it is characterized by progressive memory loss and pathologically by the accumulation of beta-amyloid peptides (Aβ) and the hyperphosphorylated Tau protein. The amyloid hypothesis is the most accepted, it postulates that the origin of the disease begins with the accumulation of Aβ, which leads to inflammatory processes, dysregulation of kinases, increase in reactive oxygen species, reduction of neuronal stem cells, loss of dendritic spines and death. neuronal, explaining dementia. It has been shown that the pharmacological activation of hepatic X receptors (LXR) in animal models of AD has produced cognitive improvement associated with increased expression of APOE and ABCA1 proteins, reduction of astrogliosis and microgliosis, protection of synaptic plasticity and dendritic spines. Natural products derived from plants have represented a promising source of bioactive molecules with multimodal characteristics for the treatment of AD, due to their high amounts of alkaloidal compounds. Zanthoxylum caribaeum is an arboreal species belonging to the Rutaceae family that has been selected after an extensive screening of Colombian plants for its high alkaloid content, LXRs agonist activity, Aβ antiaggregant, antioxidant and inhibitor of acetylcholinesterase in vitro. The objective of this work is to evaluate the effect of an ethanolic extract of Zanthoxylum caribaeum in the triple transgenic model of Alzheimer´s disease (3xTg-AD). Oral administration to triple-transgenic EA (3xTg-AD) mice and controls was performed, finding improvement in spatial memory in the Morris water maze, increased expression of ABCA1 and ApoE, reduction of expression for molecular markers of progression of the EA. Additionally, an increase in the expression of proteins associated with the synaptic function Synapsin1, Shank 1/2/3 and PSD-95 was observed. In conclusion, the effect of a crude ethanolic extract of Zanthoxylum caribaeum on the main pathophysiological markers of AD with potential therapeutic use in the 3xTg-AD model was described. proyecto: “Búsqueda racional de alcaloides isoquinolínicos del género Zanthoxylum (Rutaceae) como posibles agentes neuroprotectores para el tratamiento de la enfermedad de Alzheimer" Código 110177758004, convocatoria 777-2017" -RC-854 de 2017. Maestría Magíster en Ciencias - Bioquímica Enfermedades neurodegenerativas

Compounds extracted from essential oil of the species Zanthoxylum caribaeum were analysed by GC-MS and tested to measure the antimicrobial potential of this oil by microdilution method in broth against standard microorganisms, determine the oil antioxidant activity by the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) capture method and evaluate Dermanyssus gallinae (Panzer) (Acari: Dermanyssidae) mite repellency, tested in a Y-tube olfactometer. The GC-MS analysis identified 20 constituents, all terpenes representing 75.46 % of the essential oil total composition. The main compounds identified were α-panasinsene (12.75 %), viridiflorene (11.23 %), β-elemene (10.61 %) and β-selinene (8.72 %); all others were sesquiterpenes and a diterpene. Regarding antimicrobial activity, the essential oil was effective against all Gram-positive bacteria tested and Gram-negative strains of Salmonella enterica. The antioxidant activity values showed that there was no considerable difference between butylated hydroxytoluene (BHT) and essential oil, revealing its high antioxidant capacity of 90.22 %. In addition, the oil presented a repellent action of 79 % to the D. gallinae mite in the olfactometer tests. Finally, the study contributed to the chemical and biological characterization of the essential oil of Z. caribaeum, reporting for the first time repellent activity against D. gallinae.

As a part of our continuing search for insect and arthropod development regulators from Brazilian restinga vegetation of the Rio de Janeiro State, crude extracts, purified fractions and essential oils were submitted to screening tests seeking for biological activities on the development of the insects Rhodnius prolixus, Dysdercus peruvianus, Oncopeltus fasciatus and Rhipicephalus (Boophilus) microplus. Up to now, 102 secondary metabolites have been detected in the fractions, among them monoterpenes, sesquiterpenes and two triterpenes which were obtained from the species, Eugenia sulcata, Pilocarpus spicatus, Manilkara subsericea, Myrciaria floribunda and Zanthoxylum caribaeum. These secondary plant metabolites are considered of interest for the use of studies related to arthropod endocrinology, vector-parasite interaction system, and population control of vector insect and agricultural pest. The observed biological activities were surprisingly high, involving increased mortality, molting and metamorphosis inhibition, paralysis, corporeal deformities, apparition of permanent nymphs, of adultoids and juvenoids, partial or total inhibition of oviposition and egg hatching. These compounds are now being studied further to determine if they may or may not be useful in controlling insect populations and/or interfere with the life cycle and vector transmission of parasites to animal and human populations.

SUMMARY The present study aimed to identify and quantify the components of the essential oil of Zanthoxylum caribaeum and to evaluate the antimicrobial potential of different plant extracts and the essential oil of this plant against different serotypes of Salmonella enterica, which is of greater occurrence and isolated in the western region of Paraná, Brazil. The extraction of the essential oil was performed using Clevenger apparatus and the chemical composition was determined by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The extracts were obtained through different solvents (ethanol, methanol, hexane, acetone, dichloromethane, ethyl acetate and distilled water). The antibacterial activity was carried out according to the broth microdilution technique. The GC-MS analysis resulted in the identification of 15 main components, all terpenes, representing 63.88% of the total essential oil. The major compounds identified were Germacrene-D (20.77%), a-Panasinsene (14.40 %) and b-Selinene (11.68 %). The essential oil presented antibacterial activity against 5 serotypes of Salmonella enterica, with MIC and MBC ranging from 7000 to 437 μg.mL-1. While MIC and MBC from the range from 200 to 25 mg.mL-1, being effective to most serotypes of S. enterica, with the exception of the aqueous extract. The results suggest that the essential oil and leaf extracts of Z. caribaeum represent an alternative for the control of S. enterica in the poultry sector, in this way reflecting a new perspective for studies with natural products. RESUMO Objetivou-se com este estudo identificar e quantificar os constituintes do óleo essencial de Zanthoxylum caribaeum e avaliar o potencial antimicrobiano de diferentes extratos vegetais e do óleo essencial desta planta frente a diferentes sorotipos de Salmonella enterica, de maior ocorrência e isoladas na região oeste do Paraná, Brasil. A extração do óleo essencial foi realizada utilizando aparelho Clevenger e a composição química foi determinada por Cromatografia Gasosa acoplada a Espectrometria de Massas (CG-EM). Os extratos foram obtidos através de diferentes solventes (etanol, metanol, hexano, acetona, diclorometano, acetato de etila e água destilada). A atividade antibacteriana foi realizada segundo a técnica de microdiluição em caldo. As análises de CG-EM resultaram na identificação de 15 constituintes principais, todos terpenos, representando 63,88 % do total de óleo essencial. Os compostos majoritários identificados foram Germacreno-D (20,77 %), a-Panasinseno (14,40 %) e b-Selineno (11,68 %). O óleo essencial apresentou atividade antibacteriana frente a 5 sorotipos de Salmonella enterica, com CIM e CBM variando de 7000 a 437 µg.mL-1. Já os extratos variam a CIM e CBM de 200 a 25 mg.mL-1, sendo eficazes para a maioria dos sorotipos de S. enterica, com exceção do extrato aquoso. Os resultados sugerem que o óleo essencial e os extratos das folhas de Z. caribaeum representam uma alternativa para o controle de S. enterica, no setor avícola, refletindo uma nova perspectiva para estudos com produtos naturais.

Zanthoxylum caribaeum Lamarck (Rutaceae) is plant species with a variety of medical applications, including insecticidal activity. This study determined the bioacaricidal activity of the essential oil from Z. caribaeum leaves against engorged Rhipicephalus (Boophilus) microplus (Canestrini, 1887) females using the adult immersion test. For this purpose, three serial concentrations (5.0, 2.5, and 1.25%, vol:vol, in 1% dimetilsulfoxide) of the essential oil were used. Essential oil 5% caused 65% mortality on the first day after treatment, 85% on the second day, and 100% mortality by the fifth day. To our knowledge, this is the first demonstration of the acaricidal activity of the essential oil from Z. caribaeum leaves against cattle ticks.

"Este estudio presenta la caracterización ?toquímica y la evaluación antibacteriana y mutagénica de Erythrina herbacea, Zanthoxylum caribaeum y Dendropanax arboreus , que se utilizan en la medicina tradicional mexicana para el tratamiento de infecciones gastrointestinales y de la piel. Los extractos contienen aminas, fenoles y alcaloides principalmente al ser caracterizados por cromatografía en capa ?na. El extracto acuoso de D. arboreus y los extractos hexánicos de Z. caribaeum y E. herbacea fueron los más activos presentando CMIs de < 0.78, 0.78 y 1.56 μg/mL, respectivamente. Ninguno de los extractos tiene propiedades mutagénicas al ser evaluados con la prueba de Ames. Estos resultados sugieren que los extractos de estas plantas tienen un buen potencial para ser usados como agentes antibacterianos."

Berberis hartwegii Benth., Berberidaceae, Hamelia patens Jacq., Rubiaceae, Dendropanax arboreus (L.) Decne & Planch., Araliaceae, Erythrina herbacea L., Fabaceae, and Zanthoxylum caribaeum Lam., Rutaceae, acetone extracts were selected on the basis of their use in traditional Mexican medicine to treat scabies or skin diseases. Anti-dermatophyte activity in vitro was evaluated using the agar dilution assay, and the therapeutic efficacy of B. hartwegii and Z. caribaeum were tested against experimental tinea pedis. The infected animals were treated intragastrically daily for seven days with 2.5 and 5 mg/kg of acetone extracts. The acetone extract of H. patens exhibited 100% growth inhibition against T. mentagrophytes and E. floccosum at 100.0 and 50.0 μg/ml, respectively, and B. hartwegii inhibited growth of M. canis and T. mentagrophytes at 100.0 μg/ml. Effective treatments with 2.5 mg/kg of Z. caribaeum and B. hartwegii extract were comparable with 1 mg/kg of clotrimazole in mice. Liver profile tests and histological analyses did not exhibit any signs of toxicity and the Ames test indicated that both extracts were safe when evaluated in strains TA98, TA100 and TA102. Our results suggest the potential for the future development of new antifungal drugs from B. hartwegii or Z. caribaeum. Keywords: Antifungal activity, Berberis hartwegii, Hamelia patens, Zanthoxylum caribaeum

5-Methoxycanthin-6-one and N-methylisocorydine have been isolated from the bark of Zanthoxylum caribaeum.