ABSTRACT Spathulenol was isolated from an extract of Azorella compacta Phil., Apiaceae, by various chromatographic method; identification of the chemical structure was confirmed by comparing its spectroscopic data with those reported in the literature. The anti-Mycobacterium tuberculosis activity of spathulenol was evaluated on MDR, pre-XDR, and XDR clinical isolates of M. tuberculosis, as well as on the reference susceptible strain H37Rv and its cytotoxic activity was evaluated on the Vero Cell Line. The anti-M. tuberculosis activity of spathulenol was twice as potent against the MDR, pre-XDR, and XDR clinical isolates (6.25 µg/ml) than on the susceptible H37Rv strain (12.5 µg/ml). Additionally, the anti-M. tuberculosis activity shown by spathulenol was established as bactericidal on drug-resistant and susceptible strains of M. tuberculosis. Finally, cytotoxic activity on the Vero cell line (CC50 = 95.7 µg/ml) indicated that spathulenol is a selective anti-M. tuberculosis compound, with a selective index of 15.31 against drug-resistant clinical isolates of M. tuberculosis.

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.

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.

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.

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.