Erika Hernández-García1, Abraham García2, Elvira Garza-González3, Francisco G Avalos-Alanís4, Verónica M Rivas-Galindo5, José Rodríguez-Rodríguez6, Victor M Alcantar-Rosales7, Claudia Delgadillo-Puga8, María Del Rayo Camacho-Corona9. 1. Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, CP 66451 San Nicolás de los Garza, Nuevo León, Mexico. Electronic address: erika.hernandezgrc@uanl.edu.mx. 2. Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, CP 66451 San Nicolás de los Garza, Nuevo León, Mexico. Electronic address: edgar.garciazp@uanl.edu.mx. 3. Universidad Autónoma de Nuevo León, Servicio de Gastroenterología Hospital Universitario Dr. José Eleuterio González, Av. Gonzalitos y Madero S/N, Col. Mitras Centro, CP 64460 Monterrey, Nuevo León, Mexico. Electronic address: elvira.garzagn@uanl.edu.mx. 4. Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, CP 66451 San Nicolás de los Garza, Nuevo León, Mexico. Electronic address: Francisco.avalosal@uanl.edu.mx. 5. Universidad Autónoma de Nuevo León, Facultad de Medicina, Av. Madero S/N, Col. Mitras Centro, CP 64460 Monterrey, Nuevo León, Mexico. Electronic address: veronica.rivasgl@uanl.edu.mx. 6. Instituto Tecnológico de Estudios Superiores de Monterrey, Escuela de Ingeniería y Ciencias, Campus Monterrey, Av. 2 de Abril S/N, Tecnológico, CP 64849 Monterrey, Nuevo León, Mexico. Electronic address: jrr@itesm.mx. 7. Centro de Investigación y Asistencia en Tecnología y Diseño del Estado de Jalisco, A.C. Servicios Analíticos, Sede Noreste, Parque de Investigación e Innovación Tecnológica, Vía de la Innovación 404, CP 66628 Apodaca, Nuevo León, Mexico. Electronic address: valcantar@ciatej.mx. 8. Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán, Av. Vasco de Quiroga No. 15, Col. Belisario Domínguez Sección XVI, CP 14080 Ciudad de México, Mexico. Electronic address: claudia.delgadillop@incmnsz.mx. 9. Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, CP 66451 San Nicolás de los Garza, Nuevo León, Mexico. Electronic address: maria.camachocn@uanl.edu.mx.
Abstract
ETHNOPHARMACOLOGICAL RELEVANCE: In Mexico, plants are an important element of traditional medicine, and many are considered part of Mexican cultural heritage from prehispanic and colonial times. Nevertheless, relatively few systematic scientific studies have been conducted to fully characterize the chemical composition and pharmacological activities of Mexican medicinal plants. Acacia farnesiana is used in Mexican traditional medicine to treat dysentery and tuberculosis and therefore could have bioactive compounds that may explain its traditional use. AIMS OF THE STUDY: i) To isolate and characterize the compounds from the hexanic, chloroformic and methanolic extracts; ii) to identify the volatile compounds from methylated hexanic and chloroformic extracts using GC-FID and GC-MS methods; iii) to identify the compounds from methanolic and aqueous extracts using HPLC-Q-TOF-MS; iv) to test the activity of extracts and isolated compounds against Mycobacterium tuberculosis and dysentery bacteria. MATERIAL AND METHODS: A. farnesiana fruits were collected in Acatlán de Osorio, Puebla, Mexico. Hexanic, chloroformic, methanolic and aqueous extracts were prepared and analyzed by different chromatographic techniques including column chromatography, flash chromatography, GC-FID, GC-MS and HPLC-Q-TOF-MS. Structural elucidation was carried out by NMR spectroscopic analysis. The activity of extracts, phytochemicals and semi-synthetic derivatives against Mycobacterium tuberculosis H37Rv and G122 as well as dysentery bacteria (Campylobacter jejuni, Shigella flexneri, Salmonella enteritidis, Yersinia enterocolitica and enterohemorrhagic Escherichia coli) was determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC µg/mL). RESULTS: From both hexane and chloroform extracts, tetracosanoic acid (2S)-2,3-dihydroxypropyl ester (1) and (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2) were isolated and characterized. From the methanolic extract, methyl gallate (3), gallic acid (4), (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2), (2S) naringenin 7-O-β-glucopyranoside (prunin, 5), pinitol (6) and sucrose (7) were isolated and characterized. Furthermore, hexanic and chloroformic extracts were analyzed by GC-FID and GC-MS and 18 methylated fatty acids were identified for each extract in addition to three sterols. The methanolic and aqueous extracts were analyzed separately by HPLC-Q-TOF-MS, and 15 compounds were identified in each extract. The compounds 1, 2, and 7, in addition to 13 fatty acids and eight phenolic compounds, were identified for the first time in A. farnesiana. The extracts showed antitubercular (MIC 100-200 µg/mL) and antidysentery activity (MIC 100-200 µg/mL). Methyl gallate and its acetylated derivative showed activity against the sensible strain M. tuberculosis H37Rv with MIC values of 50-25 µg/mL, respectively. The flavanone prunin showed activity against multidrug resistant M. tuberculosis G122 (MIC 50 μg/mL). Methyl gallate, gallic acid and prunin showed activity against C. jejuni (MIC 50 μg/mL). CONCLUSIONS: The activity of tested extracts and isolated compounds against M. tuberculosis and dysentery bacteria justifies the ethnomedical use of A. farnesiana fruits for the treatment of tuberculosis and dysentery.
ETHNOPHARMACOLOGICAL RELEVANCE: In Mexico, plants are an important element of traditional medicine, and many are considered part of Mexican cultural heritage from prehispanic and colonial times. Nevertheless, relatively few systematic scientific studies have been conducted to fully characterize the chemical composition and pharmacological activities of Mexican medicinal plants. Acacia farnesiana is used in Mexican traditional medicine to treat dysentery and tuberculosis and therefore could have bioactive compounds that may explain its traditional use. AIMS OF THE STUDY: i) To isolate and characterize the compounds from the hexanic, chloroformic and methanolic extracts; ii) to identify the volatile compounds from methylated hexanic and chloroformic extracts using GC-FID and GC-MS methods; iii) to identify the compounds from methanolic and aqueous extracts using HPLC-Q-TOF-MS; iv) to test the activity of extracts and isolated compounds against Mycobacterium tuberculosis and dysentery bacteria. MATERIAL AND METHODS:A. farnesiana fruits were collected in Acatlán de Osorio, Puebla, Mexico. Hexanic, chloroformic, methanolic and aqueous extracts were prepared and analyzed by different chromatographic techniques including column chromatography, flash chromatography, GC-FID, GC-MS and HPLC-Q-TOF-MS. Structural elucidation was carried out by NMR spectroscopic analysis. The activity of extracts, phytochemicals and semi-synthetic derivatives against Mycobacterium tuberculosis H37Rv and G122 as well as dysentery bacteria (Campylobacter jejuni, Shigella flexneri, Salmonella enteritidis, Yersinia enterocolitica and enterohemorrhagic Escherichia coli) was determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC µg/mL). RESULTS: From both hexane and chloroform extracts, tetracosanoic acid (2S)-2,3-dihydroxypropyl ester (1) and (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2) were isolated and characterized. From the methanolic extract, methyl gallate (3), gallic acid (4), (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2), (2S) naringenin 7-O-β-glucopyranoside (prunin, 5), pinitol (6) and sucrose (7) were isolated and characterized. Furthermore, hexanic and chloroformic extracts were analyzed by GC-FID and GC-MS and 18 methylated fatty acids were identified for each extract in addition to three sterols. The methanolic and aqueous extracts were analyzed separately by HPLC-Q-TOF-MS, and 15 compounds were identified in each extract. The compounds 1, 2, and 7, in addition to 13 fatty acids and eight phenolic compounds, were identified for the first time in A. farnesiana. The extracts showed antitubercular (MIC 100-200 µg/mL) and antidysentery activity (MIC 100-200 µg/mL). Methyl gallate and its acetylated derivative showed activity against the sensible strain M. tuberculosis H37Rv with MIC values of 50-25 µg/mL, respectively. The flavanoneprunin showed activity against multidrug resistant M. tuberculosis G122 (MIC 50 μg/mL). Methyl gallate, gallic acid and prunin showed activity against C. jejuni (MIC 50 μg/mL). CONCLUSIONS: The activity of tested extracts and isolated compounds against M. tuberculosis and dysentery bacteria justifies the ethnomedical use of A. farnesiana fruits for the treatment of tuberculosis and dysentery.