How to Cite
Downloads
Métricas Alternativas
Dimensions
Abstract
This work reports on the study of secondary metabolites obtained by means of different extraction techniques from three Verbenaceae plants, grown in Colombia’s northeast. Lippia alba was a new chemotype not previously described in the literature. It contains carvone (40-57%) as the main component of the oils, obtained by hydrodistillation (HD) and microwave-assisted hydrodistillation (MWHD), and of the extracts isolated by simultaneous distillation-extraction (SDE), and supercritical fluid extraction (SFE). Other main components were limonene (24-37%), bicyclosesquiphellandrene (2-22%), piperitenone (1-2%), piperitone (0.8-1.2%) and ß–bourbonene (0.6-1.5%). Volatile fractions obtained by static (SHS), dynamic (purge and trap, P & T) headspace methods, or headspace-solid phase microextraction (HS-SPME), contained limonene (27-77%) as the most abundant component, followed by carvone (14-30%), bicyclosesquiphellandrene (1-33%), and ß–bourbonene (0.5-6.5%). The main components found in the essential oils (HD, MW) and extracts (SDE, SFE) of Aloysia triphylla, were neral (19-22%) and geranial (33-38%), followed by nerol (2-5%) and geraniol (2-6%), the sesquiterpenoids ar-curcumene (3-4%), bicyclosesquiphellandrene (2-3%), spathulenol (2-4%), nerolidol (ca. 2%), ß-bourbonene (1-2%), trans-ß-caryophyllene (3-5%) and its oxide (1-1.5%). The Lantana camara essential oil was of the sesquiterpenoid type; over 60% of its composition was represented by sesquiterpene hydrocarbons, C15H24, and ca. 30% by their oxygenated derivatives. trans-ß-Caryophyllene (14-15%) and its oxide (4- 9%), bicyclosesquiphellandrene (16-18%), α-zingiberene (5-6%), E,E-α-farnesene (3-4%) and γbisabolene (3-4%) were the main sesquiterpenes isolated from L. camara. The monoterpene fraction, C10H16, in L. camara did not reach 10%; ß-pinene (0.2-3%) and ß-myrcene (2-4%) were the main monoterpene hydrocarbons. While in L. alba monoterpenes (>30%) and oxygenated monoterpenes (ca. 55%) were dominant, in A. triphylla, oxygenated monoterpenes (>70%) prevailed, ca. 60% was represented by citral. On the other hand, L. camara was poor in monoterpenes and their oxygenated derivatives; most of its secondary metabolites were sesquiterpene hydrocarbons (ca. 60%) and their oxygenated derivatives (ca. 30%). The essential oils of the three Verbenaceae plants studied exhibited an in vitro antioxidant effect, which was similar or higher than those of vitamin E or BHA, when measured in a model lipid system (linoleic acid emulsio) at the same concentration, e.g. 10 g/L. L. camara oil was the most active, followed by L. alba oil.
Keywords
References
Adams, R.P. 1995. Identification of essential oil components by gas chromatography / mass spectrometry, Allured Publishing Corporation, Carol Stream, Illinois.
Bahl, J.R., Garg, S.N., Singh, S.C., Bansal, R.P., Naqvi, A.A. & Kumar, S. 2000. “Composition of linalool rich essential oil from Lippia alba grown in Indian plains” Flavour Fragr. J. 15: 199-200.
Bahl, J.R., Sinha, S., Naqvi, A.A., Bansal, R.P., Gupta, A.K. & Kumar, S. 2002. “Linalool-rich essential oil quality variants obtained from irradiated stem nodes in Lippia alba”, Flavour Fragr. J. 17: 127-132.
Bellakhdar, J., IL Idrissi, A., Cañigueral, S., Iglesias, J. & Vila, R. 1994. “Composition of lemon verbena (Aloysia triphylla (L’Herit.) Britton) oil of Moroccan origin”, J. Essent. Oil Res. 6: 523-526.
Blanco, C., Stashenko, E.E., Combariza, M.Y. & Martínez, J.R. 1995. “Comparative study of Colombian citrus oils by high-resolution gas chromatography and gas chromatography-mass spectrometry”, J. Chromatogr. A. 697: 501-513.
BrasiL E Silva, G.A. 1979. “O oleo essencial de Lippia citriodora Kunth. do Rio Grande do Sul”, Trib. Farm. 47(1): 3-5.
Carnat, A., Carnat, A.P., Fraisse, D. & Lamaison, J.L. 1999. “The aromatic and polyphenolic composition of lemon verbena tea”, Fitoterapia 70(1): 44-49.
Combariza, M.Y., Blanco, C., Stashenko, E.E. & Shibamoto, T. 1994. “Limonene concentration in lemon (Citrus volcameriana) peel oil as a function of ripeness”, J. High Resol. Chromatogr. 17: 643-646.
Davies, N.W. 1990. “Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases”, J. Chromatogr. 503: 1-24.
EL-Hamidi, A., Ahmed, S.S. & Shaarawy, F. 1983. “Lippia citriodora grown in Egypt. A new crop development”, Acta Horticulturae. 132: 31-33.
Fathy, M.M. 2000. “Comparative study of essential oils from leaves and flowers of certain Lantana species growing in Egypt”, Bull. Fac. Pharm. Cairo Univ. 38(2): 105-118.
Frankel, E.N. 1985. In: Flavor chemistry of fats and oils, D.B. Min, T.H. Smouse (Eds.), American Oil Chemists’Society.
Frei, B. (Ed.) 1994. Natural antioxidants in human health and disease, Academic Press, New York.
García Barriga, H. 1992. Flora medicinal de Colombia. Botánica médica, 2a Ed., Tercer Mundo, Bogotá.
Godefroot, M., Sandra, P. & Verzele, M. 1981. “New method for quantitative essential oil analysis”, J. Chromatogr. 203: 325-335.
Guerrera, P.M., Leporatti, M.L., Foddai, S., Moretto, D., Mercantini, R. 1995. “Antimycotic activity of the essential oil of Lippia citriodora Kunth. (Aloysia triphylla Britton)”, Rev. Italiana EPPOS. 15: 23-25.
Gupta, M.P. (Ed.) 1995. 270 Plantas medicinales Iberoamericanas, 1a Ed., CYTED-SECAB, Bogotá.
Halliwell, B. & Gutteridge, J.M.C. 1989. Free radicals I biology and medicine, Clarendon Press, Oxford.
Jennings, W. & Shibamoto, T. 1980. Qualitative analysis of flavor and fragrance volatiles by glass capillary gas chromatography, Academic Press, Inc., New York.
Joulain, D. & König, W. 1998. The Atlas of spectral data of sesquiterpene hydrocarbons, E.B.-Verlag, Hamburg.
Kovats, E. 1965. “Gas chromatographic characterization of organic substances in the retention index system”, Adv. Chromatogr. 1: 229-247.
Larson, R.A. 1997. Naturally occurring antioxidants, Lewis Publishers, Boca Raton.
Lorenzo, D., Paz, D., Davies, P., Vila, R., Cañigueral, S. & Dellacassa, E. 2001. “Composition of a new essential oil type of Lippia alba (Mill.) N. E. Brown from Uruguay”, Flavour Fragr. J. 16: 356-359.
Nakamura, I., Okuyama, E., Tsukada, A., Yamazaki, M., Satake, M., Nishibe, S., Deyama, T., Moriya, A., Maruno, M. & Nishimura, H. 1997. “Acteoside as the analgesic principle of Cedron (Lippia triphylla), a Peruvian medicinal plant”, Chem. Pharm. Bull. 45(3): 499-504.
Ngassoum, M.B., Yonkeu, S., Jirovetz, L., Buchbauer, G., Schmaus, G. & Hammerschmidt, F.-J. 1999. “Chemical composition of essential oils of Lantana camara leaves and flowers from Cameroon and Madagascar”, Flavour Fragr. J. 14: 245-250.
Oehme, M. 1998. Practical introduction to GC-MS analysis with quadrupoles, Hüthig, Heidelberg.
Özek, T., Kirimer, N., Baser, K.H.C. & Tumen, G. 1996. “Composition of the essential oil of Aloysia triphylla (L’Herit.) Britton grown in Turkey”, J. Essent. Oil Res. 8: 581-583.
Pérez, S.G., Zavala, M.A., Vargas, R., Pérez, C. & Pérez, R.M. 1998. “Antidiarrheal activity of C-9 aldehyde isolated from Aloysia triphylla”, Phytotherapy Research 12(1): S45-S46.
Pino, J.A., Ortega, A.G., Rosado, A., Rodríguez, M. & Balujar, R. 1997. “Composición y propiedades antibacterianas del aceite esencial de Lippia alba (Mill.) N. E. Brown”, Rev. Cubana Farm. 30: 1-8.
Puertas, M.P., Hillebrand, S., Stashenko, E.E. & Winterhalter, P. 2002. “In vitro radical scavenging activity of essential oils from Columbian plants and fractions from oregano (Origanum vulgare L.) essential oil”, Flavour Fragr. J. 17: 380-384.
Risch, S.J. & Chi-Tang Ho (Eds.) 1997. Spices. Flavor chemistry and antioxidant properties, ACS, Washington.
Rode, J. 2000. “Possibilities of Lippia citriodora Kunth. Cultivation in Slovenia”, Acta Horticulturae 523: 61-64.
Sefidkon, F. 2002. “Essential oil of Lantana camara L. occurring in Iran”, Flavour Fragr. J. 17: 78-80.
Senatore, F. & Rigano, D. 2001. “Essential oil of two Lippia spp. (Verbenaceae) growing wild in Guatemala”, Flavour Fragr. J. 16: 169-171
Silva, MHL, Andrade, EHA, Zoghbi, MGB, Luz, AIR, Silva, JD & Maia, JGS 1999. “Los aceites esenciales de Lantana camara L. que se encuentran en el norte de Brasil”, Flavor Fragr. J. 14: 208-210.
Stashenko, EE, Acosta, R. & Martínez, JR 2000. “Análisis cromatográfico de gases de alta resolución de los metabolitos secundarios obtenidos mediante extracción con fluidos subcríticos de la ruda colombiana (Ruta graveolens L.)”, J. Biochem. Biofísica. Métodos. 43: 379-390.
Stashenko, EE, Cervantes, M., Combariza, MY, Fuentes, H., Martínez, JR 1999. “Análisis HRGC/FID y HRGC/MSD de los metabolitos secundarios obtenidos mediante diferentes métodos de extracción de Lepechinia schiedeana, y evaluación in vitro de su actividad antioxidante”, J. High Resol. Cromatografía. 22: 343-349.
Stashenko, EE, Ferreira, C., Sequeda, G., Mateus, A., Cervantes, M. & Martínez, JR 1997. “Desarrollo de un método para monitoreo de la degradación oxidativa en lípidos y evaluación de la actividad antioxidante de productos naturales”, Arte y Ciencia Cosmética 12: 20-27.
Stashenko, EE, Ferreira, MC, Sequeda, LG, Martínez, JR & Wong, JW 1997. “Comparación de métodos de extracción y sistemas de detección en el análisis cromatográfico de gases de compuestos carbonílicos volátiles”, J. Chromatogr. A 779: 360-369.
Stashenko, EE, Macku, C. y Shibamoto, T. 1992. “Monitoreo de sustancias químicas volátiles del mosto durante la fermentación de levadura”, J. Agric. Química de los alimentos. 40: 2257-2259.
Stashenko, EE, Martínez, JR, Macku, C. & Shibamoto, T. 1993. “Análisis HRGC y GC-MS de aceite esencial de ylang-ylang colombiano (Cananga odorata Hook Fil. Et Thomson, forma genuina)”, J. Alta resolución. Cromatografía. 16: 441-444.
Stashenko, EE, Puertas, MA y Combariza, MY 1996a. “Metabolitos secundarios volátiles de Spilanthes americana obtenidos mediante destilación al vapor-extracción con solvente y extracción con fluido supercrítico simultáneamente”, J. Chromatogr. A 752: 223-232.
Stashenko, EE, Puertas, MA & Martínez, JR 2002. “Determinación SPME de aldehídos volátiles para evaluación de la actividad antioxidante in vitro”, Anal. Bioanal. Química. 373: 70-74.
Stashenko, EE, Puertas, MA, Salgar, W., Delgado, W. & Martínez, JR 2000. “Microextracción en fase sólida con derivatización en fibra aplicada al análisis de compuestos carbonílicos volátiles”, J. Chromatogr. A 886: 175-181.
Stashenko, EE, Quiroz, N. & Martínez, JR 1996b. “Estudio HRGC/FID/NPD y HRGC/MSD de aceites colombianos de ylang-ylang (Cananga odorata) obtenidos mediante diferentes técnicas de extracción”, J. High Resol. Cromatografía. 19: 353-358.
Stashenko, EE, Torres, W. & Martínez, JR 1995. “Un estudio de la variación composicional del aceite esencial de ylang-ylang (Cananga odorata Hook Fil. Et Thomson, forma genuina) durante el desarrollo floral”, J. High Resol . Cromatografía. 18: 101-104.
Stashenko, EE, Villa, HS & Combariza, MY 1995. “Estudio comparativo de aceites de ruda colombiana mediante cromatografía de gases de alta resolución utilizando diferentes sistemas de detección”, J. Microcolumn 7 de septiembre: 117-122.
Stashenko, EE, Wong, JW, Martínez, JR, Mateus, A. & Shibamoto, T. 1996c. “Cromatografía de gases de alta resolución con detección de nitrógeno-fósforo de aldehídos volátiles saturados derivatizados con 2-hidrazinobenzotiazol”, J. Chromatogr. A 752: 209-216.
Tamura, H. & Shibamoto, T. 1991. “Medición de la actividad antioxidante en un sistema de peroxidación lipídica con malondialdehído y 4-hidroxi nonenal”, J. Amer. Química del petróleo. Soc. 78: 941-943.
Tamura, H. & Yamagami, A. 1994. “Actividad antioxidante de antocianinas monoaciladas aisladas de uva Muscat Bailey A”, J. Agric. Química de los alimentos. 42: 1612-1615.
Umano, K. & Shibamoto, T. 1987. “Análisis de volátiles en el espacio de cabeza de grasa de res sobrecalentada”, J. Agric. Química de los alimentos. 35: 14-18.
Vogel, H., Silva, ML y Razmilic, I. 1999. “Fluctuación estacional del contenido de aceite esencial en hierbaluisa (Aloysia triphylla (L'Herit.) Britton)”, Acta Horticulturae 500: 75-79.
Wannmacher, L., Fuchs, FD, Paoli, CL, Fillman, HS, Gianlupi, A., Lubianca Neto, JF, Hassegawa, CY & Guimarães, FS 1990. “Plantas empleadas en el tratamiento de la ansiedad y el insomnio: II. Efecto de las infusiones de Aloysia triphylla sobre la ansiedad experimental en voluntarios normales”, Fitoterapia 61(5): 449-453.
Weyerstahl, P., Marschall, H., Eckhardt, A. & Christiansen, C. 1999. “Constituyentes del aceite de lantana brasileño comercial”, Flavor Fragr. J. 14: 15-28.
Zoghbi, MGB, Andrade, EHA, Santos, AS, Silva, MHL & Maia, JGS 1998. “Aceites esenciales de Lippia alba (Mill.) NE Br. cultivado de forma silvestre en la Amazonia brasileña”, Flavor Fragr. J. 13: 47-48.
Zygadlo, JA, Lamarque, AL, Maestri, DM, Guzmán, CA & Grosso, NR 1995. “Composición de los aceites florales de algunas especies de Lippia y Aloysia de Argentina”, J. Essent. Res. petrolera 7: 593-595.
Zygadlo, JA, Lamarque, AL, Maestri, DM, Guzmán, CA, Lucini, EI, Grosso, NR & Ariza-Espinar, L. 1994. “Constituyentes volátiles de Aloysia triphylla (L'Herit.) Britton”, J. Essent . Res. petrolera 6: 407-409.
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Copyright (c) 2023 https://creativecommons.org/licenses/by-nc-nd/4.0