Keywords
Asteraceae
essential oils
terpenoids
GC-MS
Costa Rica.
Baccharis trinervis
Asteraceae
aceites esenciales
terpenoides
GC-MS
Costa Rica.
How to Cite
Abstract
Baccharis is an Asteraceae genus of flowering plants, which has about 340 to 400 species, ranging from the Southern United States to the Southern extreme of Argentina and Chile through Central America and the Caribbean regions. The species Baccharis trinervis is a native shrub from Mexico, Central America and throughout South America. In Costa Rica, this species is commonly known as alcotán and the fresh leaves are used as a poultice on wounds and ulcers. The objective of the present research was to characterize the chemical composition of seven hydrodistilled essential oils of diverse morphological parts of B. trinervis. For this, samples were obtained from three locations in Costa Rica and standard laboratory analyses were followed. The essential oils were analyzed by capillary gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) using the retention indices on a 5 % phenyl/dimethylpolysiloxane fused silica column in addition to mass spectral fragmentation patterns, which allowed the identification of 268 compounds. The essential oils consisted mainly of terpenoids (92.3 to 97.8 %). The major constituents from the leaf oils were caryophyllene oxide (0.1-22.5 %), viridiflorol (8.8-21.0 %), germacrene D (0.5-19.1 %), germacrene B (0.2-16.0 %), β-caryophyllene (3.5-9.1 %), spathulenol (0.1-8.3 %), δ-3-carene (2.0-6.8 %), and α-pinene (2.5-5.9 %). The flower oil consisted mainly of globulol (0-24 %), β-caryophyllene (9.5-17.1 %), cis-muurola-4(14), 5-diene (traces-13.7 %), germacrene D (4.3-9.9 %), bicyclogermacrene (5.9-8.3 %), ar-curcumene (0-8.0 %), spathulenol (4.3-4.8 %), caryophyllene oxide (3.1-4.7 %), and viridiflorol (0.3-4.7 %). The major components of the branch oil were germacrene B (1.4-18.7 %), germacrene D (14.7-15.6 %), β-caryophyllene (10.1-12.4 %), viridiflorol (0-11.5 %), globulol (0.6-11.3 %), δ-3-carene (4.1-8.1 %), β-phellandrene (1.5-6.5 %), and bicyclogermacrene (3.6-4.9 %). The essential oil composition differed markedly from that of previously studied oils of plants growing in Brazil, which contain two characteristic stereoisomeric methyl dec-2-en-4,6-diynoate compounds not detected in this study. This is the first report about the chemical composition of the essential oils obtained from this species growing wild in Costa Rica.
References
Abad, M. J., Bermejo, P., Sánchez-Palomino, S., Chiriboga, X., & Carrasco, L. (1999). Antiviral activity of some South American medicinal plants. Phytotherapy Research, 13, 142-146.
Abad, M. J., & Bermejo, P. (2007). Baccharis (Compositae): a review update. ARKIVOC, Part (vii), 76-96.
Adams R. P. (2007). Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry (4th ed). Carol Stream, Illinois: Allured Publishing Corporation.
Ali, N. A. A., Wurster, M., Arnold, N., Teichert, A., Schmidt, J., Lindequist, U., & Wessjohann, L. (2008). Chemical composition and biological activities of essential oils from the oleogum resins of three endemic soqotraen Boswellia species. Records of Natural Products, 2(1), 6-12.
Albuquerque, M. R. J. R., Souza, E. B., Lins, M. U. D. S., Nogueira, N. A. P., Lemos, T. L. G., Silveira, E. R., & Pessoa, O. D. L. (2004). Composition and antimicrobial activity of the essential oil from aerial parts of Baccharis trinervis (Lam.) Pers. ARKIVOC, Part (vi), 59-65.
Bohlmann, F., & Zdero, C. (1970). Polyacetylenverbindungen. 179. Über die Inhaltsstoffe von Baccharis trinervis Pers. Chemische Berichte, 103(8), 2327-2329.
Bohlmann, F., Burkhardt, T., & Zdero, C. (1973). Naturally occurring acetylenes (pp. 215-217). London: Academic Press.
Bohlmann, F., Kramp, W., Grenz, M., Robinson, H., & King, R. M. (1981). Diterpenes from Baccharis species. Phytochemistry, 20(8), 1907-1913.
Ferracini, V. L., Paraiba, L. C., Leitao Filho, H. F., da Silva, A. G., Nascimento, L. R., & Marsaioli, A. J. (1995). Essential oils of seven Brazilian Baccharis species. Journal of Essential Oil Research, 7(4), 355-67.
Fabiane, K. C., Ferronatto, R., dos Santos, A. C., & Onofre, S. B. (2008). Physicochemical characteristics of the essential oils of Baccharis dracunculifolia and Baccharis uncinella DC. (Asteraceae). Revista Brasileira de Farmacognosia, 18(2), 197-203.
Flamini, G., Cioni, P. L, Morelli, I., Ceccarini L., Andolfi, L., & Macchia, M. (2003). Composition of the essential oil of Medicago marina L. from the coastal dunes of Tuscany, Italy. Flavour and Fragrance Journal, 18, 460-462.
Frizzo, C. D., Atti-Serafini, L., Laguna, S. E., Cassel, E., Lorenzo, D., & Dellacassa, E. (2008). Essential oil variability in Baccharis uncinella DC and Baccharis dracunculifolia DC growing wild in southern Brazil, Bolivia and Uruguay. Flavour and Fragrance Journal, 23(2), 99-106.
Heiden, G., Andrade-Baumgratz, J. F., & Esteves, R. L. (2012). Baccharis subgen. Molina (Asteraceae) no estado do Rio de Janeiro, Brasil. Rodriguésia, 63(3), 649-687.
Heras, B., Slowing, K., Benedí, J., Carretero, E., Ortega, T., Toledo, C., Bermejo, P., …, & Villar, A. (1998). Antiinflammatory and antioxidant activity of plants used in traditional medicine in Ecuador. Journal of Ethnopharmacology, 61, 161-166.
Herrera, J. C., Rosas-Romero, A. J., Crescente, O. E., Acosta, M., & Pekerar, S. (1996). Analysis of 5-hydroxy-7-methoxyflavones by normal-phase high-performance liquid chromatography. Journal of Chromatography A, 740, 201-206.
House, P. R., Lagos-Witte, S., Ochoa, L., Torres, C., Mejía, T., & Rivas, M. (1995). Plantas medicinales comunes de Honduras (pp. 50-51). Tegucigalpa, Honduras: UNAH, CIMN-H, CID/CIIR, GTZ.
Jordan, M. J., Margaria, C. C., Shaw, P. E., & Goodner, K. L. (2002). Aroma active components in aqueous Kiwi fruit essence and Kiwi fruit puree by GC-MS and multidimensional GC/GC-O. Journal of Agricultural and Food Chemistry, 50, 5386-5390.
Kuroyanagi, M., Uchida, K., Ueno, A., Satake, M., & Shimomura, K. (1993). Neo-clerodane type diterpenes from Baccharis trinervis. Phytochemistry, 34(5), 1377-1384.
León, J., & Poveda, L. J. (2000). In P. E. Sánchez-Vindas (Ed.), Nombres comunes de las plantas en Costa Rica (pp. 48). San José, Costa Rica: Editorial Guayacán.
Minteguiaga, M., Umpiérrez, N., Fariña, L., Falcão, M. A., Xavier, V. B., Cassel, E., & Dellacassa, E. (2015). Impact of gas chromatography and mass spectrometry combined with gas chromatography and olfactometry for the sex differentiation of Baccharis articulata by the analysis of volatile compounds. Journal of Separation Science, 38(17), 2931-3118.
Németh-Zámboriné, E. (2016). Natural variability of essential oil components. In K. H. C. Başir, & G. Buchbauer (Eds.). Handbook of essential oils: Science, technology, and applications (pp. 87-125). Boca Raton, FL: CRC Press/Taylor & Francis.
Núñez-Meléndez, E. (1978). Plantas medicinales de Costa Rica y su folklore. San José, Costa Rica: Editorial Universidad de Costa Rica.
Oliveira, R. N., Rehder, V. L., Oliveira, A. S. S., Júnior, I. M., de Carvalho, J. E., de Ruiz, A. L. T., Jeraldo, V. L. S., Linhares, A. X., & Allegretti, S. M. (2012). Schistosoma mansoni: In vitro schistosomicidal activity of essential oil of Baccharis trimera (Less.) DC. Experimental Parasitology, 132, 135-143.
Pittier, H. (1978). Plantas usuales de Costa Rica (reprint of 2nd ed., 1957). San José, Costa Rica: Editorial Costa Rica.
Quiroga, C. L., Ferracini, V. L., & Marsaioli, A. J. (1996). Three new oxigenated cadinanes from Baccharis Species. Phytochemistry, 42(4), 1097-1103.
Radulovic, N. S., Dordevic, N. D., & Palic, R. (2010). Volatile of Pleurospermim austriacum (L.) Hoffm. (Apiaceae). Journal of Serbian Chemical Society, 75(12), 1-11.
Ramírez-Cárdenas, A., Isaza-Mejía, G. & Pérez-Cárdenas, J. E. (2013). Especies vegetales investigadas por sus propiedades antimicrobianas, inmunomoduladoras e hipoglicemientes en el Departamento de Caldas (Colombia, Sudamérica). Biosalud, 12(1), 59-82.
Ramos Campos, F., Bressan, J., Godoy Jasinski, V. C., Zuccolotto, T., da Silva, L. E., & Bonancio Cerqueira, L. (2016). Baccharis (Asteraceae): Chemical constituents and biological activities. Chemistry and Biodiversity, 13, 1-17.
Rojas, J., Velasco, J., Morales, A., Rojas, L., Díaz, T., Rondón, M., & Carmona, J. (2008). Chemical composition and antibacterial activity of the essential oil of Baccharis trinervis (Lam.) Pers. (Asteraceae) collected in Venezuela. Natural Product Communications, 3(3), 369-372.
Sánchez-Palomino, S., Abad, M. J., Bedoya, L. M., García, J., Gonzales, E., Chiriboga, X., Bermejo, P., & Alcami, J. (2002). Screening of South American plants against human immunodeficiency virus: Preliminary fractionation of aqueous extract from Baccharis trinervis. Biological and Pharmaceutical Bulletin, 25, 1147-1150.
Sharp, H., Bartholomew, B., Bright, C., Latif, Z., Sarker, S. D., & Nash, R. J. (2001). 6-Oxygenated flavones from Baccharis trinervis (Asteraceae). Biochemical Systematics and Ecology, 29, 105-107.
Silva, F. G., Oliveira, C. B. A., Pinto, J. E. B. P., Nascimento, V. E., Santos, S. C., Seraphin, J. C., & Ferri, P. H. (2007). Seasonal variability in the essential oils of wild and cultivated Baccharis trimera. Journal of the Brazilian Chemical Society, 18(5), 990-997.
Simões-Pires, C. A., Debenedetti, S., Spegazzini, E., Mentz, L. A., Matzenbacher, N. I., Limberger, R. P., & Henriques, A. T. (2005). Investigation of the essential oil from eight species of Baccharis belonging to sect. Caulopterae (Asteraceae, Astereae): a taxonomic approach. Plant Systematics and Evolution, 253, 23-32.
Sobrinho, C. A. N., Souza, E. B., Rocha, M. F. G., Albuquerque, M. R. J. R., Bandeira, P. N., Santos, H. S., Cavalcante, C. S. P., …, & Fontenelle, R. O. S. (2016). Chemical composition, antioxidant, antifungal and hemolytic activities of essential oil from Baccharis trinervis (Lam.) Pers. (Asteraceae). Industrial Crops and Products, 84,108-115. http://dx.doi.org/10.1016/j.indcrop.2016.01.051
Sørensen, N. A. (1977). Polyacetylenes and conservatism of chemical characters in the Compositae. In V. H. Heywood, J. B. Harborne, & B. L. Turner (Eds.). The biology and chemistry of the Compositae (Vol. 1, pp. 385-409). London: Academic Press.
van den Dool, H. & Kratz, P. D. (1963). A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. Journal of Chromatography A, 11, 463-471.
Vannini, A. B., Santos, T. G., Fleming, A. C., Purnhagen, L. R. P., Lourenco, L. A., Butzke, E. T. B., Kempt, M., …, & Steindel, M. (2012). Chemical characterization and antimicrobial evaluation of the essential oils from Baccharis uncinella D.C. and Baccharis semiserrata D.C. (Asteraceae). Journal of Essential Oil Research, 24(6), 547-554.
Verdi, L. G, Brighente, I. M. C., & Pizzolatti, M. G. (2005). Gênero Baccharis (Asteraceae): aspectos químicos, económicos e biológicos. Química Nova, 28(1), 85-94. http://dx.doi.org/10.1590/S0100-40422005000100017
Zoghbi, M. G. B., Andrade, E. H. A., Santos, A. S., Silva, M. H. L., & Maia, J. G. S. (1998). Essential oils of Lippia alba (Mills.) N. E. Br. growing in the Brazilian Amazon. Flavour and Fragrance Journal, 13(1), 47-48.
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