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X-linked inhibitor of apoptosis protein (XIAP) is an emerging crucial therapeutic target in cancer. We report on the discovery and characterisation of small organic molecules from Piper genus plants exhibiting XIAP antagonism, namely erioquinol, a quinol substituted in the 4-position with an alkenyl group and the alkenylphenols eriopodols A-C. Another isolated compound was originally identified as gibbilimbol B. Erioquinol was the most potent inhibitor of human cancer cell viability when compared with gibbilimbol B and eriopodol A was listed as intermediate. Gibbilimbol B and eriopodol A induced apoptosis through mitochondrial permeabilisation and caspase activation while erioquinol acted on cell fate via caspase-independent/non-apoptotic mechanisms, likely involving mitochondrial dysfunctions and aberrant generation of reactive oxygen species. In silico modelling and molecular approaches suggested that all molecules inhibit XIAP by binding to XIAP-baculoviral IAP repeat domain. This demonstrates a novel aspect of XIAP as a key determinant of tumour control, at the molecular crossroad of caspase-dependent/independent cell death pathway and indicates molecular aspects to develop tumour-effective XIAP antagonists.

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In this work, screening of Lauraceae species for their antifungal activity against Collectotrichum tamarilloi was carried out and the ethanol extract derived from the bark of Endlicheria arenosa was found to be the best candidate. From the ethanolic extract of the bark of E. arenosa, the hexane and chloroform fractions were found to be active, from these five fatty acids were identified and two lactones were isolated. The most active fatty acid was the dodecanoic acid with a minimal inhibitory concentration (MIC) of 78.0 µM. The butyrolactone 3R,4R-licunolide A, it has not previously reported, and licunolide B show both the lowest MIC (55.3 µM). This is the first report of compounds of natural origin as growth inhibitors of C. tamarilloi.

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Ocotea is a genus that belong to Lauraceae family, which has about 56 species, distributed in Asia, Africa and mainly in America. The aim of this work was to identify the chemical composition of the essential oil from leaves of Ocotea caudata collected from Colombia. The chemical composition of the oil was determined by gas chromatography-mass spectrometry (GC-MS), being described for the first time. Thirty nine compounds (corresponding to 92.7 percent of the oil) were identified. The major constituents were germacrene D (55.8 percent), bicyclogermacrene (8.0 percent), beta-caryophyllene (4.6 percent) and beta-bourbonene (2.3 percent). Also the antibacterial activity of the oil was evaluated against two Gram (+) and two Gram (-) bacteria showing that the oil exhibited moderated activity against Gram (+) bacteria.

Resumen: Ocotea es un género perteneciente a la familia Lauraceae, que contiene cerca de 56 especies, distribuidas en Asia, Africa yprincipalmente América. El objetivo de este trabajo fue identificar la composición química del aceite esencial de las hojas de Ocoteacaudata colectadas en Colombia. La composición química del aceite fue determinada por cromatografía de gases–espectrometría de masas(GC-MS), siendo descrita por primera vez. Se identificaron treinta y nueve compuestos (correspondientes al 92.7% del aceite). Loscomponentes mayoritarios fueron germacreno D (55.8%), biciclogermacreno (8.0%), β-cariofileno (4.6%) y β-bourboneno (2.3%). Tambiénse evaluó la actividad antibacteriana del aceite frente a dos bacterias Gram (+) y dos Gram (-) encontrándose que el aceite presentómoderada actividad contra las bacterias Gram (+).

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Se caracterizaron los extractos etanólicos de hojas y cortezas de 13 especies de la familia Lauraceae mediante cromatografía en capa fina de dos dimensiones (2D-CCD). Los datos posteriores se analizaron mediante técnicas de análisis estadístico multivariado (cluster y análisis de componentes principales (PCA)). Lo anterior permitió hacer una distinción entre los extractos obtenidos de diferentes partes de la planta (hojas y cortezas). Se observó, además, que la metodología usada es capaz de diferenciar entre extractos obtenidos a partir de especies de Lauraceae y los de otras familias de plantas.

Leaves and barks ethanolic extracts from 13 Lauraceae species were characterized through two-dimensional thin layer chromatography (2D-TLC). The subsequent data was analized through multivariate statistical analysis techniques (cluster analysis and principal components analysis (PCA)). This allowed to do a distinction between extracts obtained from different parts of the plant (leaves and bark). In addition, it was observed that the implemented methodology is able to differentiate between extracts obtained from Lauraceae species and some obtained from other plant families.

Caracterizaram-se os extratos etanólicos de folhas e casca obtidos a partir de espécies da família Lauraceae por cromatografia em camada fina em duas dimensões (2D-CCF). Os dados obtidos foram analisados utilizando técnicas de análise estatística multivariada tipo análise de cluster e análise de componentes principais (PCA). As técnicas estadísticas permitiram fazer uma distinção entre os extratos obtidos a partir de diferentes partes da planta (folhas e casca). Além disso, observou-se que o método utilização é capaz de diferenciar entre os extratos provenientes de espécies de Lauraceae daqueles obtidos a partir de outras famílias de plantas.

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Introducción: Ocimum micranthum Willd, es una planta herbácea, perteneciente a la familia de las Lamiáceas, originaria de las regiones tropicales y subtropicales de América, cultivada con fines medicinales y/o ornamentales. La infusión de esta planta es usada para enfermedades de tipo gastrointestinal como úlceras, gastritis, fiebre intestinal, inflamación; disentería, vómito, dolor de estómago y vermífugo. Objetivos: determinar la composición química volátil del aceite esencial de Ocimum micranthum Willd y evaluar in vitro las actividades antifúngica, repelente, insecticida y antioxidante. Métodos : el aceite esencial (AE) fue obtenido de hojas frescas de O. micranthum por hidrodestilación, la composición química volátil fue determinada mediante cromatografía de gases acoplada a detector de espectrometría de masas (GC-MS). El ensayo de actividad fumigante (insecticida) del AE se realizó sobre Sitophilus zeamais. La actividad antifúngica sobre el hongo fitopatógeno ( Fusarium oxysporumf. sp. Dianthi), la actividad repelente contra el Tribolium castaneum Herbst y la capacidad antioxidante se efectuóa través del ensayo de decoloración del radical DPPH. Resultados: el compuesto mayoritario encontrado en el AE de O. micranthum fue el eugenol (60,37 %), seguido de eucaliptol (12,09 %), cis b-terpineol (4,25 %) y a-terpineol (4,43 %), a-cadineno (1,27 %). El AE de O. micranthum fue activo contra F. oxysporum con un porcentaje de inhibición micelar de 98,8 % a 176,5 µL de AE/L aire, leído a las 72 horas; y un porcentaje de mortalidad contra S. zeamais de 66,7 % a 500 µL de AE/L de aire, después de 24 horas de exposición. La actividad repelente fue de 92,5 % y 93,3 % a las 2 y 4 horas de exposición, respectivamente. El porcentaje de inhibición del radical DPPH• fue de 93,92 %. Conclusiones: El aceite esencial de O. micranthum mostró una significativa actividad fungicida, repelente y fumigante, por lo cual puede llegar a ser una alternativa en reemplazo de fungicidas e insecticidas sintéticos.

Introduction: Ocimum micranthum Willd is a herbaceous plant of the family Lamiaceae native to tropical and subtropical regions of America and grown for medicinal and/or ornamental purposes. Infusion of this plant is used for gastrointestinal conditions such as ulcers, gastritis, intestinal fever, inflammation, dysentery, vomiting, stomach pain and as vermifuge. Objectives: determine the volatile chemical composition of essential oil from Ocimum micranthum Willd and evaluate its in vitro antifungal, repellent, insecticidal and antioxidant activities. Methods: essential oil (EO) from O. micranthum fresh leaves was obtained by hydrodistillation. Volatile chemical composition was determined by gas chromatography coupled to a mass spectrometric detector (GC-MS). The fumigant activity assay (insecticidal) was performed against Sitophilus zeamais . Antifungal activity was determined against pathogenic fungus Fusarium oxysporum f. sp. Dianthi, and repellent activity against Tribolium castaneum Herbst. Antioxidant capacity was analyzed with the DPPH radical decolorization assay. Results: the most abundant compound found in O. micranthum EO was eugenol (60.37 %), followed by eucalyptol (12.09 %), cis-terpineol (4.25 %), a-terpineol (4.43 %), and δ-cadinene (1.27 %). O. micranthum EO was active against F. oxysporum, with a mycelial inhibition of 98.8 % at 176.5 uL EO / L air, read at 72 hours, and a mortality rate of 66.7 % against S. zeamais at 500 uL EO / L air, after 24 hours of exposure. Repellent activity was 92.5 % and 93.3 % at 2 and 4 hours of exposure, respectively. DPPH radical inhibition was 93.92 %. Conclusions: Essential oil from O. micranthum showed significant antifungal, repellent and fumigant activities. Thus it could become an alternative to replace synthetic fungicides and insecticides.

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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.

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Introducción: las plantas tienen mecanismos químicos de autoprotección para evitar ser atacadas por insectos, hongos, bacterias y virus. Las enfermedades producidas por estas plagas son controladas con plaguicidas, que presentan alta toxicidad; por esto, es necesario usar compuestos alternativos como aceites esenciales. Estas sustancias son fuentes botánicas potenciales que cumplen la misma función de los plaguicidas, con la ventaja de que presentan baja toxicidad para los mamíferos, alta volatilidad y toxicidad para los insectos y microorganismos que atacan los productos de cosecha almacenados, por ser volátiles su propiedad insecticida se conoce como fumigante. Chenopodium ambrosioides L. (Chenopodiaceae) ha sido reportada por sus potentes propiedades antiparasitarias, incluida la actividad antiprotozoaria. Objetivo: determinar la actividad fumigante, antifúngica y antioxidante del aceite esencial de Chenopodium ambrosioides y su composición química volátil. Métodos: el aceite esencial fue obtenido de hojas de C. ambrosioides por hidrodestilación, la composición química volátil se determinó mediante cromatografía de gases acoplada a espectrometría de masas. El ensayo de actividad fumigante del aceite esencial se realizó sobre Sitophilus zeamais. La actividad antifúngica sobre el hongo fitopatógeno Fusarium oxysporum f. sp. Dianthi, y la capacidad antioxidante se efectuómediante el ensayo de decoloración del radical DPPH. Resultados: el compuesto mayoritario encontrado en aceite esencial de C. ambrosioides fue a-terpineno (60,29 por ciento), seguido de p-cimeno (20,49 por ciento), 4-careno (7,96 por ciento) y trans-ascaridol (1,91 por ciento). C. ambrosioides fue activo contra Fusarium oxysporum con un porcentaje de inhibición micelar de 97,3 por ciento a 176,5 µL de aceite esencial/litro de aire, leído a las 72 h; y un porcentaje de mortalidad contra Sitophilus zeamais de 100 por ciento a 500 µL de aceite esencial/litro de aire, después de 24 h de exposición. El porcentaje de inhibición del radical DPPH• fue de 84,89 por ciento. Conclusiones: el aceite esencial de C. ambrosioides exhibió importante actividad fungicida contra F. oxysporum y fumigante contra S. zeamais, por lo cual podría reemplazar fungicidas e insecticidas sintéticos.

Introduction: plants have developed self-protecting chemical mechanisms to avoid being attacked by insects, fungi, bacteria, and viruses. The diseases caused by these pests are controlled with pesticides of high toxicity, therefore, it is necessary to use alternative compounds like essential oils. Essential oils are potential botanical sources of compounds having the same function as the pesticides. However, they have some advantages over the latter such as low toxicity for mammal, high volatility and toxicity for pests and microorganisms which attack stored products. Its volatile insecticidal property made it to be known as fumigant. Chenopodium ambrosioides L. (Chenopodiaceae) has been reported for its potential antiparasitic properties, including antiprotozoal activity. Objective: this study determine the fumigant, antifungal, and antioxidant activities of essential oils isolated from Chenopodium ambrosioides L. and their volatile chemical composition. Methods: the essential oil (EO) was obtained from leaves of C. ambrosioides by hydrodistillation whereas the volatile chemical composition was determined by gas chromatography coupled with mass spectrometry detector (GC-MS). The fumigant activity assay of the essential oil was performed against Sitophilus zeamais. The antifungal activity on plant pathogenic fungus (Fusarium oxysporum f. sp. Dianthi) and the antioxidant potential were determined through the discoloration test of DPPH. radical. Results: the major component found in the essential oil from C. ambrosioides was a-terpinene (60.29 percent), followed by p-cymene (20.49 percent), 4-carene (7.96 percent) and trans-ascaridol (1.91 percent). C. ambrosioides was active against Fusarium oxysporum, with a mycelial inhibition of 97.3 percent at 176.5 µL EO/L air after 72 h of exposure; and a mortality rate against Sitophilus zeamais of 100 percent at 500 µL of essential oil per air liter after 24 h of exposure. The inhibition percentage of DPPH• radical was 84.89 percent. Conclusions: this study demonstrated that C. ambrosioides essential oil exhibits important fungicidal activity on F. oxysporum and fumigant on S. zeamais, which could become an alternative to synthetic fungicides and insecticides.

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A series of physical and chemical changes occur as oil palm fruits ripen in the bunch. We evaluated changes in lipid content in the mesocarp and fruits, and the chemical composition of fatty acids (FA), triacylglycerol (TAG), tocols, and carotenes of the lipids extracted from fruits of three commercial tenera cultivars, namely, Deli×La Mé, Deli×Ekona, and Deli×Avros, planted in two different geographical regions in Colombia, during the ripening process 12, 14, 16, 18, 20, 22, and 24 weeks after anthesis (WAA). It was found that 12 WAA the mesocarp contained less than 6% of total lipids. Oil content increased rapidly after 16 WAA, reaching the maximum oil content of 55% in fresh mesocarp and 47% in fresh fruits at 22 WAA, which was found the optimal time for harvesting. Changes in FA and TAG showed that total polyunsaturated fatty acids (PUFA) and triunsaturated triacylglycerols (TUTAG) decreased, while total saturated fatty acids (SFA) and disaturated triacylglycerols (DSTAG) increased, over the ripening period. Changes in FA were mainly observed in palmitic, oleic, linoleic, and linolenic acids, and in POP, POO, POL, and OLL for the TAGs evaluated. Levels of tocols changed depending on whether they were tocopherols or tocotrienols. In the earliest stages tocopherols were predominant but decreased rapidly from 6600 mg kg(-1) of oil at 14 WAA to 93 mg kg(-1) of oil at 22 WAA. Tocotrienols appeared at the same time as oil synthesis started, and became the main source of total tocols, equivalent to 87% in total lipids extracted.

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El fraccionamiento bioguiado del extracto etanólico de la parte aérea de Piper septuplinervium (Piperaceae) permitió la obtención de dos substancias de tipo flavonoide, activas contra dos cepas de hongos fitopatógenos (Fusarium oxysporum f. sp. dianthiyBotrytis cinerea). Las estructuras de los compuestos aislados fueron determinadas de acuerdo con el análisis espectroscópico (RMN uni y bidimensional, EMAR). La actividad anti-fúngica fue determinada por ensayo en disco, seguido por bioautografía directa sobre las dos cepas de hongos en prueba.

Guided fractionation of ethanolic extract of aerial part of Piper septuplinervium (Piperaceae) yielded two flavonoid-type active substances against two strains of phytopathogenic fungi (Fusarium oxysporum f. sp. dianthi and Botrytis cinerea). The structures of isolated compounds were determined by spectroscopic analysis (single-and two-dimensional NMR, HRMS). The antifungal activity was determined by disk test, followed by direct bioautography against the two strains of fungi tested.

O fracionamento bio-guiado do extrato etanólico da parte aérea de Piper septuplinervium (Piperaceae) permitiuobter duas substâncias flavonóidesativas contra duas linhagens de fungos patogênicos (Fusarium oxysporum f. sp. Dianthi e Botrytis cinerea). Mediante a análise espectroscópica (RMN mono e bidimensional, RMS) determinaram-se as estruturas desses compostos. A atividade antifúngica foi determinada pelo teste de disco, seguido por bio-autografia direta sobre duas inhagens fúngicas testadas.

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OBJECTIVES: New anti-mycobacterial entities with novel mechanisms of action are clinically needed for treating resistant forms of tuberculosis. The purpose of this study was to evaluate anti-tubercular activity and selectivity of seven recently isolated natural products from Colombian plants. METHODS: MICs were determined using a liquid medium growth inhibition assay for Mycobacterium tuberculosis H(37)Rv and both solid and liquid media growth inhibition assays for Mycobacterium bovis BCG. Escherichia coli growth inhibition and mammalian macrophage cell toxicity were evaluated to establish the degree of selectivity of the natural product against whole cell organisms. Enzymatic inhibition of ATP-dependent MurE ligase from M. tuberculosis was assayed using a colorimetric phosphate detection method. The most active compound, 3-methoxynordomesticine hydrochloride, was further investigated on M. bovis BCG for its inhibition of sigmoidal growth, acid-fast staining and viability counting analysis. RESULTS: Aporphine alkaloids were found to be potent inhibitors of slow-growing mycobacterial pathogens showing favourable selectivity and cytotoxicity. In terms of their endogenous action, the aporphine alkaloids were found inhibitory to M. tuberculosis ATP-dependent MurE ligase at micromolar concentrations. A significantly low MIC was detected for 3-methoxynordomesticine hydrochloride against both M. bovis BCG and M. tuberculosis H(37)Rv. CONCLUSIONS: Considering all the data, 3-methoxynordomesticine hydrochloride was found to be a potent anti-tubercular compound with a favourable specificity profile. The alkaloid showed MurE inhibition and is considered an initial hit for exploring related chemical space.

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En este estudio se determinó la composición química de los aceites esenciales de hojas de Ocotea longifolia y O. macrophylla obtenidos mediante destilación por arrastre convapor, yse evaluó la actividad antifúngica e insecticida de los aceites esenciales para estimar su uso como posibles plaguicidas. El rendimiento del aceite esencial de O. longifolia fue superior al 0,2%, mientras que el rendimiento del aceite esencial de O. macrophylla fue inferior al 0,1%. El análisis de los aceites por CG/EM permitió la identificación de α-terpinoleno (80,91%) y α-felandreno (4,74%) como componentes principales del aceite O. longifolia, y espatulenol (15,91%), γ-muuroleno (15,4%) y biciclogermacreno (14,58%) como los principales componentes de O. macrophylla. El aceite esencial de O. longifolia mostró actividad fumigante significativa contra Sitophilus zeamais (CL50 280,5 µL/L aire). Adicionalmente se evaluó la actividad antifúngica de los aceites esenciales, encontrándose un bajo efecto inhibidor en el crecimiento de los hongos fitopatógenos Fusarium oxysporum f. sp. dianthi y Botrytis cinerea.

This study determined the chemical composition of the essential oils isolated from leaves of Ocotea longifolia and O. macrophylla by steam distillation and the antifungal and insecticide activities of essential oils as potential pesticides were tested. The yield of essential oil of O. longifolia was more than 0.2%, while the essential oil yield of O. macrophylla was less than 0.1%. GC/MS analysis allowed the identification of α-terpinolene (80.91%) and α-phellandrene (4.74%) as the main constituents of O. longifolia oil, and spathulenol (15.91%), γ-muurolene (15.4%) and bicyclogermacrene (14.58%) as the major constituents of O. macrophylla. The essential oil of O. longifolia showed significant fumigant activity against Sitophilus zeamais (LC50 280.5 µL/L air), and could become an alternative to synthetic pesticides for controlling this pest. The antifungal activity of the essential oils also was evaluated. The essential oils showed low inhibitory effect on the growth of the phytopathogen fungi Fusarium oxysporum f. sp. dianthi and Botrytis cinerea.

Neste estudo nós determinamos a composicào química dos óleos essenciais das folhas de Ocotea longifolia e O. macrophylla obtidas por destilacáo a vapor e avaliaram a atividade antifúngica e inseticida de óleos essenciais para estimar a sua possível utilizacào como pesticidas. O rendimento do óleo essencial de O. longifolia foi superior a 0,2%, enquanto o rendimento doóleo essencial de O. acrophylla foi inferior a 0,1%. A análise dos óleos por CG/EM permitiu a identificacáo de α-terpinolene (80,91%) e α-felandreno (4,74%) como os principais componentes do óleo de O. longifolia, e espatulenol (15,91%), γ-muuroleno (15,4%) e biciclogermacreno (14,58%) como os principais componentes do óleo de O. macrophylla. O óleo essencial de O. longifolia mostraram atividade significativa contra Sitophilus zeamais (CL50 280,5 µL/L ar), e pode se tornar uma alternativa aos inseticidas sintéticos para o controle desta praga. A atividade antifúngica de óleos essenciais também foi avaliada. Os óleos essenciais de O. longifolia e O. macrophylla apresentaram baixo efeito inibitório sobre o crescimento dos fungos Fusarium oxysporum f. sp. dianthi e Botrytis cinerea.