Synergistic Antifungal Effect and In Vivo Toxicity of a Monoterpene Isoespintanol Obtained from Oxandra xylopioides Diels.

Candida sp. infections are a threat to global health, with high morbidity and mortality rates due to drug resistance, especially in immunocompromised people. For this reason, the search for new alternatives is urgent, and in recent years, a combined therapy with natural compounds has been proposed. Considering the biological potential of isoespintanol (ISO) and continuing its study, the objective of this research was to assess the effect of ISO in combination with the antifungals fluconazole (FLZ), amphotericin B (AFB) and caspofungin (CASP) against clinical isolates of C. tropicalis and to evaluate the cytotoxic effect of this compound in the acute phase (days 0 and 14) and chronic phase (days 0, 14, 28, 42, 56, 70 and 84) in female mice (Mus musculus) of the Balb/c lineage. The results show that ISO can potentiate the effect of FLZ, AFB and CASP, showing synergism with these antifungals. An evaluation of the mice via direct observation showed no behavioral changes or variations in weight during treatment; furthermore, an analysis of the cytokines IFN-γ and TNF in plasma, peritoneal cavity lavage (PCL) and bronchoalveolar lavage (BAL) indicated that there was no inflammation process. In addition, histopathological studies of the lungs, liver and kidneys showed no signs of toxicity caused by ISO. This was consistent with an analysis of oxaloacetic transaminases (GOT) and pyruvic transaminases (GPT), which remained in the standard range. These findings indicate that ISO does not have a cytotoxic effect at the doses evaluated, placing it as a monoterpene of interest in the search for compounds with pharmacological potential.

Cytotoxic Potential of the Monoterpene Isoespintanol against Human Tumor Cell Lines.

Cancer is a disease that encompasses multiple and different malignant conditions and is among the leading causes of death in the world. Therefore, the search for new pharmacotherapeutic options and potential candidates that can be used as treatments or adjuvants to control this disease is urgent. Natural products, especially those obtained from plants, have played an important role as a source of specialized metabolites with recognized pharmacological properties against cancer, therefore, they are an excellent alternative to be used. The objective of this research was to evaluate the action of the monoterpene isoespintanol (ISO) against the human tumor cell lines MDA-MB-231, A549, DU145, A2780, A2780-cis and the non-tumor line MRC-5. Experiments with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and fluorescence with propidium iodide (PI), 4',6-diamidino-2-phenylindole dilactate (DAPI) and green plasma revealed the cytotoxicity of ISO against these cells; furthermore, morphological and chromogenic studies revealed the action of ISO on cell morphology and the inhibitory capacity on reproductive viability to form colonies in MDA-MB-231 cells. Likewise, 3D experiments validated the damage in these cells caused by this monoterpene. These results serve as a basis for progress in studies of the mechanisms of action of these compounds and the development of derivatives or synthetic analogues with a better antitumor profile.

Transcriptional Reprogramming of Candida tropicalis in Response to Isoespintanol Treatment.

Candida tropicalis, an opportunistic pathogen, ranks among the primary culprits of invasive candidiasis, a condition notorious for its resistance to conventional antifungal drugs. The urgency to combat these drug-resistant infections has spurred the quest for novel therapeutic compounds, with a particular focus on those of natural origin. In this study, we set out to evaluate the impact of isoespintanol (ISO), a monoterpene derived from Oxandra xylopioides, on the transcriptome of C. tropicalis. Leveraging transcriptomics, our research aimed to unravel the intricate transcriptional changes induced by ISO within this pathogen. Our differential gene expression analysis unveiled 186 differentially expressed genes (DEGs) in response to ISO, with a striking 85% of these genes experiencing upregulation. These findings shed light on the multifaceted nature of ISO's influence on C. tropicalis, spanning a spectrum of physiological, structural, and metabolic adaptations. The upregulated DEGs predominantly pertained to crucial processes, including ergosterol biosynthesis, protein folding, response to DNA damage, cell wall integrity, mitochondrial activity modulation, and cellular responses to organic compounds. Simultaneously, 27 genes were observed to be repressed, affecting functions such as cytoplasmic translation, DNA damage checkpoints, membrane proteins, and metabolic pathways like trans-methylation, trans-sulfuration, and trans-propylamine. These results underscore the complexity of ISO's antifungal mechanism, suggesting that it targets multiple vital pathways within C. tropicalis. Such complexity potentially reduces the likelihood of the pathogen developing rapid resistance to ISO, making it an attractive candidate for further exploration as a therapeutic agent. In conclusion, our study provides a comprehensive overview of the transcriptional responses of C. tropicalis to ISO exposure. The identified molecular targets and pathways offer promising avenues for future research and the development of innovative antifungal therapies to combat infections caused by this pathogenic yeast.

Isoespintanol Antifungal Activity Involves Mitochondrial Dysfunction, Inhibition of Biofilm Formation, and Damage to Cell Wall Integrity in Candida tropicalis.

The growing increase in infections caused by C. tropicalis, associated with its drug resistance and consequent high mortality, especially in immunosuppressed people, today generates a serious global public health problem. In the search for new potential drug candidates that can be used as treatments or adjuvants in the control of infections by these pathogenic yeasts, the objective of this research was to evaluate the action of isoespintanol (ISO) against the formation of fungal biofilms, the mitochondrial membrane potential (ΔΨm), and its effect on the integrity of the cell wall. We report the ability of ISO to inhibit the formation of biofilms by up to 89.35%, in all cases higher than the values expressed by amphotericin B (AFB). Flow cytometric experiments using rhodamine 123 (Rh123) showed the ability of ISO to cause mitochondrial dysfunction in these cells. Likewise, experiments using calcofluor white (CFW) and analyzed by flow cytometry showed the ability of ISO to affect the integrity of the cell wall by stimulating chitin synthesis; these changes in the integrity of the wall were also observed through transmission electron microscopy (TEM). These mechanisms are involved in the antifungal action of this monoterpene.

Bioactividad e identificación de los ácidos grasos de la esponja marina Tetilla rodriguesi (Tetractinellida: Tetillidae) en el Caribe colombiano / Bioactivity and identification of fatty acids of the marine sponge Tetilla rodriguesi (Tetractinellida: Tetillidae) in the Colombian Caribbean

Resumen Introducción: Durante millones de años, los organismos marinos han venido desarrollando estrategias para adaptarse a los cambios ambientales y con esto, sintetizando una gran variedad de metabolitos secundarios con actividades biológicas. Objetivo: Evaluar las actividades antimicrobiana y antioxidante e identificar los ácidos grasos del extracto metanólico de la esponja marina Tetilla rodriguesi recolectada en la bahía de Cispatá. Métodos: Los especímenes de T. rodriguesi se sometieron a extracción para obtener el extracto metanólico, del cual se obtuvieron los ácidos grasos que fueron esterificados e identificados haciendo uso de técnicas cromatográficas. Con el extracto metanólico se realizó la actividad antioxidante frente a los radicales ABTS+• y DPPH• y la actividad antimicrobiana por el método de microdilución frente a cepas de referencia de Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Enterococcus faecalis y Candida albicans; además de aislados clínicos de Candida albicans (obtenida en sangre) y Candida krusei (obtenida en catéter). Resultados: Los resultados arrojaron la identificación de 19 ácidos grasos de diferente naturaleza. En el análisis de la actividad antioxidante se pudo encontrar, que la inhibición de los radicales evaluados fue moderada (296.98 ppm para ABTS+• y 3 523.62 ppm para DPPH•). La evaluación de la actividad antimicrobiana mostró, que el extracto metanólico de T. rodriguesi logró reducir en gran medida el crecimiento de todos los microorganismos evaluados. Conclusión: A pesar de que los poríferos tienden a poseer ácidos grasos de gran tamaño, en este trabajó no se encontró la presencia de ácidos grasos de cadena carbonada mayor a 20 miembros. Los resultados de la actividad antioxidante, se asemejan en gran medida al encontrado en otras especies del mismo phylum. En esta investigación, se pudo establecer que el extracto metanólico de T. rodriguesi logró disminuir en gran medida el crecimiento de todas las cepas bacterianas y fúngicas utilizadas.

Abstract Introduction: For millions of years, organisms that inhabit the marine environment have been developing strategies to adapt to environmental changes and with this, synthesizing a great variety of secondary metabolites with biological activities. Objective: Evaluate the antimicrobial and antioxidant activities and identify the fatty acids of the methanolic extract of the marine sponge Tetilla rodriguesi collected in Cispatá bay, Colombian Caribbean. Methods: T. rodriguesi specimens were subjected to extraction to obtain the methanolic extract, of which the fatty acids were obtained, esterified and identified it using chromatographic techniques. With the methanolic extract, the antioxidant activity was carried out against the radicals ABTS+• and DPPH•, and the antimicrobial activity by the microdilution method against reference strains of Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Enterococcus faecalis and Candida albicans; in addition to clinical isolates of Candida albicans (obtained in blood) and Candida krusei (obtained in catheter). Result: The results yielded the identification of 19 fatty acids of different nature. In the analysis of the antioxidant activity could be found that inhibition of radical evaluated was moderate (296.98 ppm for ABTS+• and 3 523.62 ppm for DPPH•). The evaluation of antimicrobial activity showed that the methanol extract of T. rodriguesi managed to greatly reduce the growth of all microorganisms tested. Conclusions: Despite the fact that porifers tend to have large fatty acids, in this study the presence of fatty acids with a carbon chain greater than 20 members was not found. The result of antioxidant activity is largely resembled that found in other species of the same phylum. In this research, it was established that the methanolic extract of T. rodriguesi managed to greatly reduce the growth of all the bacterial and fungal strains used.

Antibacterial Screening of Isoespintanol, an Aromatic Monoterpene Isolated from Oxandra xylopioides Diels.

The incidence of nosocomial infections, as well as the high mortality and drug resistance expressed by nosocomial pathogens, especially in immunocompromised patients, poses significant medical challenges. Currently, the efficacy of plant compounds with antimicrobial potential has been reported as a promising alternative therapy to traditional methods. Isoespintanol (ISO) is a monoterpene with high biological activity. Using the broth microdilution method, the antibacterial activity of ISO was examined in 90 clinical isolates, which included 14 different species: (Escherichia coli (38), Pseudomonas aeruginosa (12), Klebsiella pneumoniae (13), Acinetobacter baumannii (3), Proteus mirabilis (7), Staphylococcus epidermidis (3), Staphylococcus aureus (5), Enterococcus faecium (1), Enterococcus faecalis (1), Stenotrophomonas maltophilia (2), Citrobacter koseri (2), Serratia marcescens (1), Aeromonas hydrophila (1), and Providencia rettgeri (1). MIC90 minimum inhibitory concentration values ranged from 694.3 to 916.5 µg/mL and MIC50 values from 154.2 to 457.3 µg/mL. The eradication of mature biofilms in P. aeruginosa after 1 h of exposure to ISO was between 6.6 and 77.4%, being higher in all cases than the percentage of biofilm eradication in cells treated with ciprofloxacin, which was between 4.3 and 67.5%. ISO has antibacterial and antibiofilm potential against nosocomial bacteria and could serve as an adjuvant in the control of these pathogens.

Mechanism of Antifungal Action of Monoterpene Isoespintanol against Clinical Isolates of Candida tropicalis.

The growing increase in infections by Candida spp., non-albicans, coupled with expressed drug resistance and high mortality, especially in immunocompromised patients, have made candidemia a great challenge. The efficacy of compounds of plant origin with antifungal potential has recently been reported as an alternative to be used. Our objective was to evaluate the mechanism of the antifungal action of isoespintanol (ISO) against clinical isolates of Candida tropicalis. Microdilution assays revealed fungal growth inhibition, showing minimum inhibitory concentration (MIC) values between 326.6 and 500 µg/mL. The eradication of mature biofilms by ISO was between 20.3 and 25.8% after 1 h of exposure, being in all cases higher than the effect caused by amphotericin B (AFB), with values between 7.2 and 12.4%. Flow cytometry showed changes in the permeability of the plasma membrane, causing loss of intracellular material and osmotic balance; transmission electron microscopy (TEM) confirmed the damage to the integrity of the plasma membrane. Furthermore, ISO induced the production of intracellular reactive oxygen species (iROS). This indicates that the antifungal action of ISO is associated with damage to membrane integrity and the induction of iROS production, causing cell death.

Caracterización de los ácidos grasos y actividad antimicrobiana del extracto en metanol de Holothuria princeps (Holothuriida: Holothuriidae) / Characterization of fatty acids and antimicrobial activity of the methanol extract of Holothuria princeps (Holothuriida: Holothuriidae)

Introduction: In recent decades, studies related to the search and characterization of bioactive molecules in marine organisms have increased exponentially, demonstrating the enormous wealth of secondary metabolites of diverse structural composition that cannot be found in organisms present in the terrestrial environment. A significant number of the new marine natural compounds discovered have contributed to solving some of the problems of humanity, mainly those related to human health. Objective: The purpose of this research is to evaluate the bactericidal and fungicidal activities of the methanolic extract of sea cucumber Holothuria princeps collect from the bay of Cispatá in the Colombian Caribbean, in addition to chemically identifying its fatty acids. Methods: A methanolic extraction was performed from the collected biological material, by the cold maceration method. The extract obtained was fractionated using chromatographic techniques and the fatty acids were obtained, which were derivatized and identified by means of gas chromatography in coupling with mass spectrometry. The antibacterial and antifungal activities of the methanolic extract of Holothuria princeps was performed through the microdilution method against reference strains and clinical isolates. Results: We found 16 fatty acids present in Holothuria princeps according to the analysis of their mass spectra. Antibacterial activity showed that Enterococcus faecalis was the most susceptible to the extract at low concentrations, while Pseudomonas aeruginosa was the highest at the higher concentrations. In antifungal treatment, the fungus with the highest inhibition was the clinical isolate of Candida albicans (blood sample). Conclusions: Taking into account previous studies in the genus Holothuria, it is considered that the environment plays a fundamental role in the presence and diversity of fatty acids. The evaluation of the antibacterial activity against reference strains of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae and Enterococcus faecalis demonstrated the existence of a considerable effect in the reduction of bacterial growth by the extracts applied, mainly at low concentrations (less than 1 000 ppm). On the other hand, the antifungal activity against the reference strain of Candida albicans and the clinical isolates of Candida albicans (blood sample) and Candida krusei (catheter sample), the extract showed that the best results were presented at higher concentrations (above 1 500 ppm).

Introducción: En las últimas décadas los estudios relacionados con la búsqueda y caracterización de moléculas bioactivas en organismos marinos han aumentado de una manera exponencial, lo que demuestra la enorme riqueza de metabolitos secundarios de diversa composición estructural que no pueden ser encontrados en organismos presentes en el medio terrestre. Estas nuevas moléculas halladas poseen numerosas actividades biológicas que ayudan a resolver muchos problemas que ha tenido el hombre a lo largo de su existencia, lo que las convierte en productos de gran importancia para la humanidad. Objetivo: El propósito de este estudio es la identificación de los ácidos grasos presentes en el pepino de mar Holothuria princeps recolectado en costas del Caribe colombiano, además del análisis de las actividades antibacterianas y antifúngicas de su extracto metanólico frente a cepas de referencia y aislados clínicos. Métodos: Del material biológico recolectado se realizó una extracción metanólica usando el método de maceración en frío. El extracto obtenido se fraccionó usando cromatografía en columna y se lograron obtener los ácidos grasos, los cuales fueron derivatizados e identificados por medio de cromatografía de gases en acople con espectrometría de masas. La actividad antibacteriana y antifúngica del extracto metanólico de Holothuria princeps se realizó a través del método de microdilución. Resultados: Los resultados arrojaron la identificación de 16 ácidos grasos presentes en Holothuria princeps de acuerdo con el análisis de sus espectros de masas. La actividad antibacteriana mostró que Enterococcus faecalis fue la bacteria más susceptible al efecto del extracto a bajas concentraciones, mientras que a las más altas lo fue Pseudomonas aeruginosa. A nivel general en el tratamiento antifúngico, el hongo que presentó una mayor inhibición fue el aislado clínico de Candida albicans (muestra de sangre). Conclusiones: Teniendo en cuenta estudios previos en organismos del mismo género, se puede considerar en cuanto a los ácidos grasos identificados, que el entorno juega un papel fundamental en la presencia y composición de estos compuestos. La evaluación de la actividad antibacteriana contra cepas de referencia de Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae y Enterococcus faecalis, demostró la existencia de un efecto considerable en la reducción del crecimiento bacteriano por parte de los extractos utilizados, principalmente a bajas concentraciones (menos de 1 000 ppm). En cuanto

Perfil lipídico y ensayos de las actividades antioxidante, insecticida y antialimentaria de la esponja marina Iotrochota birotulata (Iotrochotidae: Demospongiae) / Lipid profile and assays of the antioxidant, insecticide and antifeedant activities of the marine sponge Iotrochota birotulata (Iotrochotidae: Demospongiae)

Resumen Los mares ocupan aproximadamente tres cuartas partes de la tierra constituyendo el hábitat de una gran cantidad de especies de flora y fauna. Como parte de los organismos marinos, los phylum bioquímicamente más estudiados son Porífera, Cnidaria y más recientemente Ascomycota, de todos ellos se han aislado e identificado un gran número de compuestos químicos, los cuales han mostrado diferentes tipos de actividades biológicas, principalmente citotóxica, bactericida y antioxidante, entre otras. En esta investigación se estudió la esponja marina Iotrochota birotulata recolectada en Punta Bello-Córdoba en el Caribe colombiano lográndose determinar su perfil lipídico a partir del análisis de los correspondientes espectros de masas de sus compuestos constituyentes, fueron identificados 19 ácidos grasos, los cuales son reportados por primera vez para esta especie. Además fueron identificados 10 esteroles. Se encontraron ácidos grasos con cadenas carbonadas entre C15 y C27, mostrando una amplia diversidad estructural lo cual es característico del phylum porífera. En cuanto a los esteroles se encontraron estructuras principalmente con núcleos Δ5 y Δ7 que son los más abundantes en las esponjas. Se encontró moderada actividad antioxidante en la estabilización del catión radical ABTS+• y baja actividad en la estabilización del radical DPPH•, el mayor valor de inhibición se encontró en el extracto acuoso con un valor de IC50 de 43.9 µg/ml frente al catión radical ABTS+•, mostrando que I. birotulata puede producir compuestos con moderada actividad antioxidante. En el ensayo de actividad insecticida, se encontró afectación larval en los extractos metanólico y acuoso en todas las concentraciones y en todos los tiempos de exposición evaluados frente a Spodoptera frugiperda, también se determinó que estos extractos inducen un efecto antialimentario en las larvas como parte del mecanismo insecticida. Se determinaron las condiciones y los tiempos de exposición óptimos para la mejor eficiencia del ensayo, las cuales fueron de 3 000 µg/ml y 48 h para el extracto metanólico y 2 000 µg/ml y 24 h para el extracto acuoso, respectivamente. En conclusión, los extractos evaluados de I. birotulata mostraron moderada actividad antioxidante y buenas e interesantes actividades insecticida y antialimentaria.(AU)

Abstract It is estimated that three quarters of earth´s surface is occupied by the oceans. This constitutes the habitat of a large number of species of flora and fauna. As part of the marine organisms, the most studied biochemical phylum are Porifera, Cnidaria and more recently Ascomycota, from which a large number of chemical compounds have been isolated and identified. These have shown different types of biological activities, mainly cytotoxic, bactericidal and antioxidant. In this research the marine sponge Iotrochota birotulata collected in Punta Bello-Córdoba in the Colombian Caribbean was studied, and its lipid profile from the analysis of the corresponding mass spectra of its constituent compounds was determined, 19 fatty acids were identified, which are reported for the first time for this specie, besides 10 sterols were identified. Fatty acids with carbon chains between C15 and C27 were found, showing a wide structural diversity, which is characteristic of the porifera phylum. The sterols showed structures mainly with nucleus Δ5 and Δ7, which are the most abundant in sponges. Moderate antioxidant activity was found in the stabilization of the radical cation ABTS+• and low activity in the stabilization of the radical DPPH•, the highest inhibition value was found in the aqueous extract with an IC50 de 43.9 µg/ml against the radical cation ABTS+•, showing that I. birotulata can produce compounds with moderate antioxidant activity. In the insecticidal activity test, larval affectation was found in methanolic and aqueous extracts at all concentrations and at all times of exposure evaluated against Spodoptera frugiperda, it was also determined that these extracts induce an antifeedant effect on the larvae as part of the mechanism insecticide. The optimal conditions and exposure times were determined for the best efficiency of the assay, which were 3 000 µg/ml and 48 h for the methanolic extract and 2 000 µg/ml and 24 h for the aqueous extract, respectively. In conclusion, the evaluated extracts of the I. birotulata showed moderate antioxidant activity and good and interesting insecticidal and antifeedant activities.(AU)

Estudio fitoquímico y evaluación de la actividad antioxidante de Esenbeckia litoralis Donn.Sm. (Loro grande) / Phytochemical study and evaluation of the antioxidant activity of Esenbeckia litoralis Donn. Sm. (loro)

Introducción: la especie Esenbeckia litoralis Donn.Sm. (Rutaceae) es también conocida como Loro o Loro grande, ha sido empleado en la medicina tradicional para el tratamiento de mordeduras de serpientes, dolor de garganta y lesiones ocasionadas por picaduras de insectos. Esta variedad de actividades son causadas por acción de los compuestos que la constituyen, como lignanos, terpenos, alcaloides, cumarinas y polifenoles que representan un alto potencial farmacológico para esta especie. Objetivo: realizar el estudio fitoquímico y evaluación de la actividad antioxidante de la especie E. litoralis. Métodos: los extractos vegetales de hojas corteza y madera se obtuvieron empleando etanol al 96 por ciento, y posteriormente fueron fraccionados usando técnicas cromatográficas como Cromatografía en Capa Delgada (CCD), Cromatografía en Columna (CC) y Cromatografía en Capa Delgada Preparativa (CCDP). Los compuestos se identificaron mediante el análisis de datos espectroscópicos con el empleo de técnicas instrumentales como: Infrarrojo (IR), Resonancia Magnética Nuclear Protónica y de Carbono trece (RMN-1H y 13C), Espectrometría de Masas (EM) y difracción de rayos x (DRX). La actividad antioxidante se evaluó a través de los métodos radical catiónico ABTS•+, radical libre DPPH• y Potencial de Actividad de Reducción Férrica (FRAP). Resultados: de esta especie se aislaron e identificaron cinco compuestos: cuatro alcaloides y un flavonoide. Los extractos en acetato de etilo de hojas y corteza mostraron una significativa actividad frente a los radicales ABTS•+ con un IC50 de 5,65 y 7,65 µg/mL respectivamente. Conclusiones: de los distintos extractos se aislaron cinco compuestos: 1-hidroxi-3-metoxi-N-metilacridona (1), maculosidina (2) maculina (3), dictamina (4) y gardenina B (5). El extracto en acetato de etilo de hojas y corteza presentaron una significativa actividad antioxidante frente al radical ABTS con un IC50 de 5,65 y 7,65 mg/L, respectivamente(AU)

Introduction: The species Esenbeckia litoralis Donn. Sm. (Rutaceae), also known as loro or loro grande, has been used in traditional medicine to treat snakebites, sore throats and lesions caused by insect bites. The compounds contained in the plant, among them lignans, terpenes, alkaloids, coumarins and polyphenols, are responsible for such a broad variety of activities, granting it great pharmacological potential. Objective: Conduct a phytochemical study and evaluation of the antioxidant activity of the species E. litoralis. Methods: Plant extracts from leaves, stem and wood were obtained using 96 percent ethanol, and then fractioned with chromatographic techniques such as thin-layer chromatography (TLC), column chromatography (CC) and preparative thin-layer chromatography (PTLC). The compounds were identified by spectroscopic data analysis using instrumental techniques such as infrared (IR) spectroscopy, proton and Carbon-13 nuclear magnetic resonance (NMR-1H and 13C), mass spectrometry (MS) and X-ray diffraction (XRD). Antioxidant activity was evaluated with the methods ABTSo+ radical cation, DPPHo free radical and ferric reducing ability power (FRAP). Results: Five compounds were isolated from the species: four alkaloids and one flavonoid. Ethyl acetate extracts from leaves and stem displayed significant activity against ABTSo+ radicals, with a CI50 of 5.65 and 7.65 µg/ml, respectively. Conclusions: Five compounds were isolated from the various extracts: 1-hydroxy-3-methoxy-N-methylacridone (1), maculosidin (2), maculin (3), dictamin (4) and gardenin B (5). The leaf and stem extract in ethyl acetate displayed significant antioxidant activity against the ABTS radical, with a CI50 of 5.65 and 7.65 mg/l, respectively(AU)

Estudio fitoquímico y evaluación de la actividad antioxidante de Esenbeckia litoralis Donn.Sm. (Loro grande) / Phytochemical study and evaluation of the antioxidant activity of Esenbeckia litoralis Donn. Sm. (loro)

Introducción: la especie Esenbeckia litoralis Donn.Sm. (Rutaceae) es también conocida como Loro o Loro grande, ha sido empleado en la medicina tradicional para el tratamiento de mordeduras de serpientes, dolor de garganta y lesiones ocasionadas por picaduras de insectos. Esta variedad de actividades son causadas por acción de los compuestos que la constituyen, como lignanos, terpenos, alcaloides, cumarinas y polifenoles que representan un alto potencial farmacológico para esta especie. Objetivo: realizar el estudio fitoquímico y evaluación de la actividad antioxidante de la especie E. litoralis. Métodos: los extractos vegetales de hojas corteza y madera se obtuvieron empleando etanol al 96 por ciento, y posteriormente fueron fraccionados usando técnicas cromatográficas como Cromatografía en Capa Delgada (CCD), Cromatografía en Columna (CC) y Cromatografía en Capa Delgada Preparativa (CCDP). Los compuestos se identificaron mediante el análisis de datos espectroscópicos con el empleo de técnicas instrumentales como: Infrarrojo (IR), Resonancia Magnética Nuclear Protónica y de Carbono trece (RMN-1H y 13C), Espectrometría de Masas (EM) y difracción de rayos x (DRX). La actividad antioxidante se evaluó a través de los métodos radical catiónico ABTS•+, radical libre DPPH• y Potencial de Actividad de Reducción Férrica (FRAP). Resultados: de esta especie se aislaron e identificaron cinco compuestos: cuatro alcaloides y un flavonoide. Los extractos en acetato de etilo de hojas y corteza mostraron una significativa actividad frente a los radicales ABTS•+ con un IC50 de 5,65 y 7,65 µg/mL respectivamente. Conclusiones: de los distintos extractos se aislaron cinco compuestos: 1-hidroxi-3-metoxi-N-metilacridona (1), maculosidina (2) maculina (3), dictamina (4) y gardenina B (5). El extracto en acetato de etilo de hojas y corteza presentaron una significativa actividad antioxidante frente al radical ABTS con un IC50 de 5,65 y 7,65 mg/L, respectivamente(AU)

Introduction: The species Esenbeckia litoralis Donn. Sm. (Rutaceae), also known as loro or loro grande, has been used in traditional medicine to treat snakebites, sore throats and lesions caused by insect bites. The compounds contained in the plant, among them lignans, terpenes, alkaloids, coumarins and polyphenols, are responsible for such a broad variety of activities, granting it great pharmacological potential. Objective: Conduct a phytochemical study and evaluation of the antioxidant activity of the species E. litoralis. Methods: Plant extracts from leaves, stem and wood were obtained using 96 percent ethanol, and then fractioned with chromatographic techniques such as thin-layer chromatography (TLC), column chromatography (CC) and preparative thin-layer chromatography (PTLC). The compounds were identified by spectroscopic data analysis using instrumental techniques such as infrared (IR) spectroscopy, proton and Carbon-13 nuclear magnetic resonance (NMR-1H and 13C), mass spectrometry (MS) and X-ray diffraction (XRD). Antioxidant activity was evaluated with the methods ABTSo+ radical cation, DPPHo free radical and ferric reducing ability power (FRAP). Results: Five compounds were isolated from the species: four alkaloids and one flavonoid. Ethyl acetate extracts from leaves and stem displayed significant activity against ABTSo+ radicals, with a CI50 of 5.65 and 7.65 µg/ml, respectively. Conclusions: Five compounds were isolated from the various extracts: 1-hydroxy-3-methoxy-N-methylacridone (1), maculosidin (2), maculin (3), dictamin (4) and gardenin B (5). The leaf and stem extract in ethyl acetate displayed significant antioxidant activity against the ABTS radical, with a CI50 of 5.65 and 7.65 mg/l, respectively(AU)

Actividad antibacteriana y antifúngica de la estrella de mar Oreaster reticulatus (Valvatida: Oreasteridae) y de los erizos de mar Mellita quinquiesperforata (Clypeasteroida: Mellitidae) y Diadema antillarum (Diadematoida: Diadematidae) del Caribe Colombiano / Antibacterial and antifungal activity of the starfish Oreaster reticulatus (Valvatida: Oreasteridae) and the sea urchins Mellita quinquiesperforata (Clypeasteroida: Mellitidae) and Diadema antillarum (Diadematoida: Diadematidae) from the Colombian Caribbean

Resumen Como organismos bentónicos, estrellas de mar y erizos de mar están constantemente expuestos a un gran número de bacterias, hongos y virus, algunos de ellos potencialmente dañinos. Para sobrevivir, estos equinodermos dependen de su sistema inmunológico, que ha desarrollado una serie de compuestos que actúan como estrategias de defensa antimicrobianos. En este trabajo se evaluaron las actividades antibacteriana y antifúngica de los extractos metanólicos de la estrella de mar Oreaster reticulatus y de los erizos de mar Mellita quinquiesperforata y Diadema antillarum recolectados en el Caribe Cordobés, frente a las bacterias Escherichia coli, Staphylococcus aureus y Klebsiella pneumoniae, y frente a los hongos fitopatógenos Fusarium sp., Scleortium sp., y Rhizoctonia sp. Los resultados obtenidos mostraron que O. reticulatus y D. antillarum, son organismos capaces de producir compuestos con capacidad antibiótica generando inhibición bacteriana a bajas concentraciones (< 100 µg / ml), mientras que M. quinquiesperforata no presentó inhibición a ninguna de la concentraciones evaluadas. Específicamente, la cepa de S. aureus fue la que presentó mayor susceptibilidad frente a los extractos evaluados, es decir, los metabolitos producidos por los equinodermos inhiben con mayor facilidad las bacterias Gram +. Por su parte, solo el extracto de diclorometano de D. antillarum presentó inhibición frente a Fusarium sp., con porcentajes de inhibición de 78.2 % y 56.5 % a concentraciones de 2 000 y 100 µg / ml. Se encontró que las cepas de los hongos Sclerotium sp. y Rhizoctonia sp., presentaron resistencia frente a todos los.extractos de los organismos estudiados, con excepción del extracto de diclorometano de D. antillarum.

Abstract As benthic organisms, sea stars and sea urchins are constantly exposed to a large number of bacteria, fungi and viruses, some of them potentially harmful. To survive, these echinoderms depend on their immune system, which has developed a number of compounds which act as antimicrobial defense strategies. In this work, the antibacterial and antifungal activities of the extracts of the starfish Oreaster reticulatus and sea urchins Diadema antillarum and Mellita quinquiesperforata collected in the Caribbean Cordobés were evaluated against the bacteria Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae and against the phytopathogenic fungi Fusarium sp., Scleortium sp., and Rhizoctonia sp. Our results show that O. reticulatus and D. antillarum produce compounds producing bacterial inhibition at low concentrations (< 100 μg / ml), while, M. quinquiesperforata extracts showed no inhibition at any of the concentrations tested. Specifically, the strain of S. aureus was the one with greater susceptibility to the extracts evaluated, i.e. the metabolites produced by echinoderms inhibit more easily gram + bacteria. Only the D. antillarum dichloromethane affected Fusarium sp. with inhibition of 78.2 % and 56.5 % at concentrations of 2 000 and 100 μg / ml. Strains of the fungi Sclerotium sp. and Rhizoctonia sp. had resistance to all extracts. Rev. Biol. Trop. 63 (Suppl. 2): 329-337. Epub 2015 June 01.

Relación entre la composición química y la actividad antioxidante del aceite esencial de Ocimum basilicum L. cultivado bajo diferentes tratamientos de fertilizante / Relationship between the chemical composition and the antioxidant activity of essential oil of Ocimum basilicum L. grown under different fertilizer treatments

Introducción: la albahaca, Ocimum basilicum L. (Lamiaceae), es originaria del Asia meridional, principalmente de la India. Esta planta es conocida por sus propiedades medicinales. El aceite esencial es utilizado para el tratamiento de la depresión y otros problemas neurológicos, es considerada como una especie promisoria en cuanto al aprovechamiento industrial de su aceite esencial. Objetivos: determinar las variaciones en el rendimiento, la composición química y actividad antioxidante del aceite esencial de Ocimum basilicum L., cultivada bajo distintos tratamientos de fertilizante. Métodos: plantas de Ocimum basilicum L. se cultivaron bajo 3 tratamientos de fertilización diferentes. Un grupo control sin fuente orgánica o inorgánica, y 2 con diferentes concentraciones de fuente orgánica pero con la misma de inorgánica. El aceite esencial de las plantas adultas se obtuvo mediante destilación por arrastre con vapor y su composición química se determinó por cromatografía de gases acoplada a espectrometría de masas. La actividad antioxidante del aceite se midió usando el ensayo de 1,1-difenil-2-picrilhidrazilo. Las comparaciones entre medias de diferentes grupos se hicieron utilizando ANOVA. Resultados: el rendimiento del aceite esencial no fue influenciado por el tratamiento con fertilizantes, este presentó alta proporción de compuestos aromáticos (estragol y eugenol) y monoterpenos oxigenados (linalool y eucaliptol). Hubo variación significativa en el contenido de eugenol y en la actividad antioxidante del aceite esencial de acuerdo con el tratamiento de fertilización. Conclusiones: de acuerdo con la composición química, el aceite esencial de Ocimum basilicum es clasificado como de quimiotipo egipcio. Su actividad antioxidante in vitro hace de esta planta una fuente interesante para su aplicación como antioxidante natural, en particular, cuando es cultivada sin aplicación de fertilizante.

Introduction: Ocimum basilicum L. (Lamiaceae) known as albahace, is native from southern Asia, mainly from India.This plant is known for its medicinal properties. The essential oil is used to treat depression and other neurological problems, being considered as a promising species in terms of the industrial utilization of that oil. Objectives: to determine variations in yield, chemical composition and antioxidant activity of the essential oil of Ocimum basilicum L., grown under distinct fertilizer treatments. Methods: Ocimum basilicumL. plants were grown under three different fertilizer treatments. A control group without organic or inorganic source, and two groups with different concentrations of organic sources but with the same concentration of inorganic source. The essential oil of adult plants was obtained The steam distillation served to obtain the adult plant's essential oil and the gas chromatography coupled to mass spectrometry method determined its chemical composition. The antioxidant activity was measured using the 1,1-diphenyl-2-pycrilhydrazil assay. The comparisons of the means of the three groups were made with ANOVA. Results: the yield of the essential oil was not influenced by the fertilizer treatment. It showed high proportion of aromatic compounds (estragole and eugenol) and oxygenated monoterpenes (linalool and eucalyptol). There was significant variation in the content of eugenol and in the antioxidant activity according to the fertilizer treatment. Conclusions: according to the chemical composition, the essential oil of Ocimum basilicum is classified as the Egyptian chemotype. The in vitro antioxidant activity of the essential oil makes this plant an interesting natural antioxidant, in particular, when it is grown without fertilizer.