ABSTRACT Calea urticifolia (Mill.) DC., Asteraceae, is a native plant of the Yucatan Peninsula used in traditional medicine to treat inflammation and pain. The bioassay-guided purification of the ethanol root extract allowed the isolation of the main bioactive metabolites, which were identified as an inseparable mixture of thymol (1) and 3-methyl-4-isopropylphenol (2), together with 3,4-O-dicaffeoylquinic acid methyl ester (3), 3,4-O-dicaffeoyl-epi-quinic acid methyl ester (4), 3,5-O-dicaffeoyl-epi-quinic acid methyl ester (5) and 3,5-O-dicaffeoylquinic acid (6). The results showed that the analgesic activity detected in the root extract of C. urticifolia could be attributed mainly to the mixture of 1 and 2 and to the novel 3,4-O-dicaffeoyl-epi-quinic acid methyl ester (4). Alternatively, the similarity on the antiinflammatory and antioxidant activities of the dicaffeoylquinic acid derivatives 3–5 suggests that the former might be related to their ability as radical scavengers.

A number of metabolites isolated and identified from cuticular waxes have been used as chemotaxonomical markers and to explain the role of the wax layer in plant-insect and plant-pathogen interactions. Chromatographic analysis of the cuticular wax from pinnae of five coconut palm ecotypes showed that the three main components (I, II, III) in the wax can be used as chemotaxonomical markers for classification. The positive correlation found between the content of metabolites I, II, and III in the wax from the various ecotypes and their resistance or susceptibility to the lethal yellowing disease of coconut palms, did not coincide with the results obtained in an antifeedant assay. The results suggest that while the individual components do not play a significant role in the palm-insect interaction, the full composition of the cuticular wax does.

Un número de metabolitos aislados e identificados de ceras epicuticulares se han utilizado como marcadores quimiotaxonómicos y para explicar el papel de las ceras en las interacciones planta-insecto y planta patógeno. El análisis cromatográfico de la cera epicuticular de las pinas de cinco ecotipos de cocotero mostró que los tres componentes principales (I, II, III) en la cera se pueden utilizar como marcadores quimiotaxonómicos de clasificación. La correlación positiva entre el contenido de los metabolitos I, II y III en la cera de los diferentes ecotipos y su resistencia o susceptibilidad a la enfermedad del amarillamiento letal en palmas de cocotero, no coincidió con los resultados obtenidos en un bioensayo de actividad antialimentaria. Los resultados sugieren que mientras los componentes puros no juegan un papel importante en la interacción palma-insecto, la composición total de la cera epicuticular si lo hace.

A purificação do extrato da raiz de Colubrina greggii var. yucatanensis levou ao isolamento e identificação do ácido 3-O-acetil ceanótico, um novo triterpeno natural, juntamente com os metabólitos já descritos: ácido ceanótico, ácido cenoténico, ácido betulínico, discarina B e crisofaneína. Os produtos naturais e os derivados semi-sintéticos éster de acetil dimetil ceanotato, dimetil ceanotato e peracetato de crisofaneína mostraram moderada a baixa atividade leishmanicida e tripanocida. Nenhum dos metabólitos mostrou ser citotóxicos ou ter atividade antiproliferativa. Os resultados também sugerem que o ácido betulínico contribui para a atividade antiplasmódica inicialmente detectada na raiz do extrato bruto de C. greggii var. yucatanensis.

Purification of the root extract of Colubrina greggii var. yucatanensis resulted in the isolation and identification of 3-O-acetyl ceanothic acid as a new natural ceanothane triterpene, together with the known metabolites ceanothic acid, cenothenic acid, betulinic acid, discarine B and chrysophanein. The natural products and the semisynthetic esters acetyl dimethyl ceanothate, dimethyl ceanothate and chrysophanein peracetate showed moderate to low leishmanicidal and trypanocidal activities. None of the metabolites showed cytotoxic or antiproliferative effects. The results also suggested that betulinic acid contributes to the antiplasmodial activity originally detected in the crude root extract of C. greggii var. yucatanensis.

Purification of the wax extract from leaves of Cnidoscolus aconitifolius (Miller) I.M. Johnston resulted in the isolation and identification of three triterpenoids: amyrenone (1), β-amyrin acetate (2) and α-amyrin acetate (3); additionally two separate fractions containing a mixture of β and α amyrin (4 and 5) and an unidentified number of alkanes, were also obtained. Metabolites were identified by comparing their spectral data with those from authentic samples and/or with those reported in the literature.

La purificación del extracto ceroso de las hojas de Cnidoscolus aconitifolius (Miller) I.M. Johnston resultó en el aislamiento e identificación de tres triterpenoides: amirenona (1), acetato de β-amirina (2) y acetato de α-amirina (3); además de dos fracciones adicionales conteniendo una mezcla de β y α amirina (4 y 5) y un número desconocido de alcanos. Los metabolitos fueron identificados por comparación de sus datos espectroscópicos con los de los estándares respectivos y/o con los reportados en la literatura.

Purification of the ethyl acetate extract of the mycelium of Alternaria tagetica resulted in the isolation of two major components, identified as ergosterol endoperoxide (1) and a complex mixture of triglicerides (5a-5f). While the former was identified by comparing its spectroscopic data with those in the literature, individual triglicerides were identified after careful analysis of their FABMS data and the results obtained from the GC/MS analysis of their hydrolysis products.

La purificación del extracto de acetato de etilo del micelio de Alternaria tagetica resultó en el aislamiento de dos componentes mayoritarios, identificados como endoperóxido de ergosterol (1) y una mezcla compleja de triglicéridos (5a-5f). La identificación se realizó mediante la comparación de sus datos espectroscópicos con los de la literatura. Los triglicéridos fueron identificados después de un análisis cuidadoso de sus datos de FABMS y los resultados obtenidos en el análisis de GC/MS de sus productos hidrolizados.

The three major components present in the epicuticular wax from leaves of Cocos nucifera L. were identified as lupeolmethylether (1), skimmiwallin (2) [3β-methoxy-25-ethyl-9,19-cyclolanost-24(24¹)-ene] and isoskimmiwallin(3) [3β-methoxy-24-ethyl-9,19-cyclolanost-25(25¹)-ene]. Structural elucidation of the metabolites was carried out by analysis of their spectroscopic data and/or by comparison with those reported in the literature.

Los tres componentes principales presentes en la cera epicuticular de Cocos nucifera L. fueron identificados como el éter metílico de lupeol (1), skimmiwallina (2) [3β-metoxi-25-etil-9,19-ciclolanost-24(24¹)-eno] e isoskimmiwallina (3) [3β-metoxi-24-etil-9,19-ciclolanost-25(25¹)-eno]. La elucidación estructural de estos metabolitos se llevó a cabo mediante la interpretación de sus datos espectroscópicos y/o por comparación de los mismos con los reportados en la literatura.