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.

Two new ent-kaurane diterpenes, 1-hydroxy-18-nor-kaur-4,16-dien-3-one (1) and 15-hydroxy-kaur-16-en-3-one (2), along with the four known metabolites kaur-16-en-19-ol (3), kaurenoic acid (4), merilactone (5), and ribenone (6), and a mixture of stigmasterol and β-sitosterol were isolated from the ethanolic root extract of Chiococca alba. Chemical structures of the different metabolites were established through the interpretation of their spectroscopic data and/or by comparing them with those reported in the literature.

Dos nuevos diterpenos tipo ent-kaurano, 1-hidroxi-18-nor-kaur-4,16-dien-3-ona (1) y 15-hidroxi-kaur-16-en-3-ona (2), además de cuatro metabolitos ya conocidos, kaur-16-en-19-ol (3), ácido kaurenoico (4), merilactona (5), y ribenona (6), y una mezcla de estigmasterol y β-sitosterol, fueron aislados del extracto etanólico de la raíz de Chiococca alba. Las estructuras químicas de los diferentes metabolitos fueron establecidas mediante la interpretación de sus datos espectroscópicos y/o por comparación con los datos reportados en la literatura.

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.

Kaempferol-3-rutinoside (1), together with α-amyrin, β-amyrin, acetato de taraxasterilo and stigmastenol, were isolated from the organic crude extract of the leaves of Sideroxylon foetidissimum subsp. gaumeri. Identification of the various metabolites was carried out by analyzing their spectroscopic data and/or by comparing it with those reported in the literature.

Kaempferol-3-rutinósido (1), además de α-amirina, β-amirina, acetato de taraxas-terol y estigmastenol, fueron aislados del extracto orgánico crudo de las hojas de Sideroxylon foetidissimum. La identificación de los diferentes metabolitos se llevó a cabo mediante el análisis de sus datos espectroscópicos y/o por comparación de los mismos con los reportados en la literatura.

Blumenol A (1), blumenol B (2) and loliolide (3), together with the ubiquitous β-sitosterol, α-amyrin and β-amyrin, were isolated from the organic extract of the leaves of Heliotropium angiospermum. Structural elucidation of the metabolites was carried out by analysis of their spectroscopic data and/or by comparison with those reported in the literature.

Blumenol A, blumenol B y loliólido, además de β-sitosterol, α-amirina y β-amirina, fueron aislados del extracto orgánico de las hojas de Heliotropium angiospermum. La elucidación estructural de los 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.

Two natural isocordoin derivatives, dihydroisocordoin (1) and flemistrictin B (2), were isolated from the root extract of Lonchocarpus xuul. Both metabolites were identified on the basis of their spectroscopic data and by comparing them with those reported in the literature.

Del extracto de la raíz de Lonchocarpus xuul fueron aislados dos derivados naturales de isocordoína, dihidroisocordoína (1) y flemistrictina B (2). Ambos metabolitos fueron identificados con base en sus datos espectroscópicos y por comparación de los mismos con los reportados en la literatura.

The methanolic extract of the root of Colubrina greggii S. Watson showed antimicrobial activity against Bacillus subtilis and Staphylococcus aureus. The bioassay-guided purification of the organic crude extract resulted in the isolation and identification of chrysophanol (1,8-dihydroxy-3-methylanthracenedione), as the metabolite responsible for the antimicrobial activity.

El extracto metanólico de las raíces de Colubrina greggii S. Watson mostró actividad antibacteriana contra Bacillus subtilis y Staphylococcus aureus. La purificación biodirigida del extracto orgánico crudo de las raíces permitió el aislamiento y la identificación de crisofanol (1,8-dihydroxy-3-methylanthracenediona) como el metabolito responsable de la actividad antimicrobiana.

Duas novas flavanonas naturais, 5-hidroxi-6,7-(2",2"-dimetilcromeno)flavanone (1) e 5-metoxi-3-hidroxi-6,7-(2",2"-dimetilcromeno)flavanone (2), foram isoladas dos extratos das raízes de L. yucatanensis e L. xuul, respectivamente. Adicionalmente, quatro novos metabólitos, os flavanóides glicosídicos quercetina-3-ramnoglucosídeo e caempferol-3-ramnoglucosídeo, juntamente com 4-hidroxi-N-metil-prolina, e o éster metílico do ácido p-cumárico, foram isolados pela primeira vez das folhas de L. xuul. Os metabólitos foram identificados usando os dados espectroscópicos obtidos e pela comparação desses com aqueles encontrados na literatura.

Two new natural flavanones, 5-hydroxy-6,7-(2",2"-dimethylchromene)flavanone (1) and 5-methoxy-3-hydroxy-6,7-(2",2"-dimethylchromene)flavanone (2), were isolated from the root extracts of L. yucatanensis and L. xuul, respectively. Additionally, four known metabolites, the glycosidic flavonoids quercetin-3-rhamnoglucoside and kaempferol-3-rhamnoglucoside, together with 4-hydroxy-N-methyl-proline, and p-coumaric acid methyl ester, were isolated for the first time from the leaves of L. xuul. The various metabolites were identified on the basis of their spectroscopic data and by comparison with those reported in the literature.

The methanolic extracts of roots and leaves of Jatropha gaumeri showed antimicrobial and antioxidant activity, respectively. The bioassay-guided purification of the root extract resulted in the isolation and identification of 2-epi-jatrogrossidione (1), a rhamnofolane diterpene with antimicrobial activity, and of 15-epi-4E-jatrogrossidentadione (2), a lathyrane diterpene without biological activity. Similarly, the bioassay-guided purification of the crude leaf extract allowed the identification of β-sitosterol and the triterpenes α-amyrin, β-amyrin and taraxasterol, as the metabolites responsible for the antioxidant activity. We wish to report here the isolation of the metabolites mentioned above and the complete assignment, not reported to date, of the 13C NMR signals for 1.

Los extractos metanólicos de la raíz y hojas de Jatropha gaumeri mostraron actividad antimicrobiana y antioxidante, respectivamente. La purificación biodirigida del extracto de la raíz resultó en el aislamiento e identificación de 2-epi-jatrogrossidiona (1), un diterpeno tipo rhamnofolano con actividad antimicrobiana contra B. subtilis, y de 15-epi-4E-jatrogrossidentadiona (2), un diterpeno tipo lathyrano sin actividad en este ensayo. De manera similar, la purificación biodirigida del extracto crudo de las hojas permitió identificar al β-sitosterol y a los triterpenos α-amirina, β-amirina y taraxasterol como los responsables de la actividad antioxidante. En este trabajo se reporta el aislamiento de los productos mencionados y la asignación completa, no reportada hasta ahora, de las señales de RMN-13C de 1.

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.