Chemistry of essential oils of the shrub Lippia alba (Verbenaceae) from Mexico and Costa Rica

Chemistry of essential oils of the shrub Lippia alba (Verbenaceae) from Mexico and Costa Rica

Authors

  • Carlos Chaverri 1. Universidad de Costa Rica, Escuela de Química, San José 11501-2060, Costa Rica. 2. Universidad de Costa Rica, Centro de Investigaciones en Productos Naturales (CIPRONA), San José 11501-2060 Costa Rica. https://orcid.org/0000-0002-0260-994X
  • Feliza Ramón-Farías Universidad Veracruzana, Facultad de Ciencias Biológicas y Agropecuarias. Apartado Postal 177, 94500, Córdoba, Veracruz, México https://orcid.org/0000-0003-4567-7333
  • José F. Cicció 1. Universidad de Costa Rica, Escuela de Química, San José 11501-2060, Costa Rica. 2. Universidad de Costa Rica, Centro de Investigaciones en Productos Naturales (CIPRONA), San José 11501-2060 Costa Rica. https://orcid.org/0000-0003-4550-2090

DOI:

https://doi.org/10.22458/urj.v14i2.4005

Abstract

ABSTRACT: Introduction: Lippia is a Verbenaceous genus of flowering plants, which has about 200 species, distributed throughout the southern USA, Mexico, and Central America to South America. Objective: To study and compare the chemical compositions of the essential oils of L. alba growing in Mexico and Costa Rica. Methods: The essential oils were obtained by hydrodistillation in a Clevenger-type apparatus. The chemical composition of the oils was analyzed by capillary GC-FID and GC-MS using the retention indices on a DB-5 type capillary column in addition to mass spectral fragmentation patterns. Results: A total of 65 compounds were identified in the essential oil samples from both countries, accounting for 96,5-98,1% of the total amount of the oils. The main constituents of the Mexican sample were 1,8-cineole (22,3%), myrcenone (11,2%), myrcene (10,9%), (E)-ocimenone (10,7%), (Z)-ocimenone (7,5%), and sabinene (6,8%), while for essential oil from Costa Rica the major compounds were myrcenone (30,4%), 1,8-cineole (21,4%), myrcene (11,0%), hedycaryol (4,4%), and sabinene (4,3%). Samples from both countries can be classified as belonging to chemotype “tagetenone”. Lippia alba (strong form) from Costa Rica produces essential oil that differs from all other essential oils of L. alba studied to date because it contained the sesquiterpenoids hedycaryol and the isomeric alcohols α-eudesmol, β-eudesmol, and γ-eudesmol. Conclusion: L. alba (strong form) from Costa Rica can be classified as a new subtype of the chemotype “tagetenone” (chemotype II).

References

Adams, R. P. (2007). Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry (4th Ed.). Allured Publishing Corporation.

Amaral, U. do, Ballesteiro, M., Corrêa, P., Alves de Souza, A., & Bajay, M. M. (2017). Polymorphism in Lippia alba clones from the Metropolitan Region of Rio de Janeiro. Journal of Advance in Agriculture, 7(2), 1044-1049. https://doi.org/10.24297/jaa.v7i2.6221

Atkins, S. (2004). Verbenaceae. In J. W. Kadereit (Ed.), The families and genera of flowering plants (Vol. 7, pp. 449-468). Springer-Verlag.

Barbosa, F. G., Lima, M. A. S., & Silveira, E. R. (2005). Total NMR assignments of new [C7-O-C7”]-biflavones from leaves of the limonene-carvone chemotype of Lippia alba (Mill.) N. E. Brown. Magnetic Resonance in Chemistry, 43(4), 334-338. https://doi.org/10.1002/mrc.1546

Barbosa, F. G., Lima, M. A. S., Braz-Filho, R., & Silveira, E. R. (2006). Iridoid and phenylethanoid glycosides from Lippia alba. Biochemical Systematics and Ecology, 34(11), 819-821. https://doi.org/10.1016/j.bse.2006.06.006

Cáceres, A. (1996). Plantas de uso medicinal en Guatemala. Editorial Universidad de San Carlos de Guatemala.

Cicció, J. F., & Ocampo, R. A. (2004). Aceite esencial de Lippia alba (Verbenaceae) cultivada en el trópico húmedo en el Caribe de Costa Rica. Ingeniería y Ciencia Química, 21(1-2), 13-16.

Cicció, J. F., & Ocampo, R. A. (2006). Variación anual de la composición química del aceite esencial de Lippia alba (Verbenaceae) cultivada en Costa Rica. Lankesteriana, 6(3), 147-152. https://doi.org/10.15517/LANK.V010.7960

Cicció, J. F., & Ocampo, R. (2010). Distribución biogeográfica de Lippia alba (Mill.) N.E. Br. ex Britton & Wilson y quimiotipos en América y el Caribe. In E. Dellacassa (Ed.), Normalización de productos naturales obtenidos de especies de la Flora Aromática Latinoamericana (pp. 107-130). Editora Universitaria da PUCRS.

Cornwell, C. P., Reddy, N., Leach, D. N., & Willie, S. G. (2000). Hydrolysis of hedycaryol: the origin of the eudesmols in the Myrtaceae. Flavour and Fragrance Journal, 15(6), 421-431. https://doi.org/10.1002/1099-1026(200011/12)15:6˂421::AID-FFJ933˃3.0.CO;2-G

Farias M. R., Pértile R., Correa, M. M., de Almeida, M. T. R., Palermo J., & Schenkel, E. P. (2010). Triterpenoid saponins from Lippia alba (Mill.) N. E. Brown. Journal of the Brazilian Chemical Society, 21(5), 927-933. https://doi.org/10.1590/S0103-50532010000500023

Filho, J. G. S., Duringer, J. M., Uchoa, D. E. A., Xavier, H. S., Filho, J. M. B., & Filho, R. B. (2007). Distribution of iridoid glycosides in plants from the genus Lippia (Verbenaceae): An investigation of Lippia alba (Mill.) N. E. Brown. Natural Product Communications, 2(7), 715-716. https://doi.org/10.1177/1934578X0700200701

Fischer, U., López, R., Pöll, E., Vetter, S., Novak, J., & Franz, C. M. (2004). Two chemotypes within Lippia alba populations in Guatemala. Flavour and Fragrance Journal, 19(4),333-335. https://doi.org/10.1002/ffj.1309

Germosén-Robineau, L. (Ed.). (2005). Farmacopea vegetal caribeña. (2nd Ed.). Editorial Universitaria UNAN.

Gilbert, B., Pinto-Ferreira, J. L., & Ferreira-Alves, L. (2005). Monografias de plantas medicinais brasileiras e aclimatadas. Abifito.

Gómez, L. D. (1986). Vegetación de Costa Rica: Vol. 1: Apuntes para una biogeografía costarricense. Editorial Universidad Estatal a Distancia.

Gupta, M. P. (Ed.). (1995). 270 plantas medicinales iberoamericanas. CYTED-SECAB.

Hennebelle, T., Sahpaz, S., Dermont, C., Joseph, H., & Bailleul, F. (2006a). The essential oil of Lippia alba: Analysis of samples from French Overseas Departments and review of previous works. Chemistry and Biodiversity, 3(10), 1116-1125. https://doi.org/10.1002/cbdv.200690113

Hennebelle, T., Sahpaz, S., Joseph, H., & Bailleul, F. (2006b). Phenolics and iridoids of Lippia alba. Natural Product Communications, 1(9), 727-730. https://doi.org/10.1177/1934578X0600100906

Hennebelle, T., Sahpaz, S., Joseph, H., & Bailleul, F. (2008). Ethnopharmacology of Lippia alba. Journal of Ethnopharmacology, 116(2), 211-222. https://doi.org/10.1016/j.jep.2007.11.044

House, P. R., Lagos-Witte, S., Ochoa, L., Torres, C., Mejías, T., & Rivas, M. (1995). Plantas medicinales comunes de Honduras. Universidad Nacional Autónoma de Honduras.

Jones, R. V. H., & Sutherland, M. D. (1968). Hedycaryol, the precursor of elemol. Chemical Communications, 1229-1230. https://doi.org/10.1039/C19680001229

Lopes, J. M. L., de Carvalho, H. H., Zorzatto, C., Azevedo, A. L. S., Machado, M. A., Salimena, F. R. G., Grazul, R. M., Gitzendanner, M. A., Soltis, D. E., Soltis, P. S., & Viccini, L. (2020). Genetic relationships and polyploid origins in the Lippia alba complex. American Journal of Botany, 107(3), 466-476. https://doi.org/10.1002/ajb2.1443

Morton, J. F. (1981). Atlas of medicinal plants of Middle America. Bahamas to Yucatan. Charles C Thomas Pub Ltd.

Munir, A. A. (1993). A taxonomic revision of the genus Lippia (Houst. ex.) Linn. (Verbenaceae) in Australia. Journal of the Adelaide Botanic Gardens, 15(2), 129-145. www.jstor.org/stable/23874023

Núñez, E. (1975). Plantas medicinales de Costa Rica y su folklore. Editorial Universidad de Costa Rica.

Polatoğlu, K. (2013). “Chemotypes” -A fact that should not be ignored in natural product studies. The Natural Products Journal, 3(1), 10-14. https://doi.org/10.2174/2210315511303010004

Reis, A. C., Sousa, S. M., Vale, A. A., Pierre, P. M., Franco A. L., Campos, J. M., Vieira, R. F., & Viccini, L. F. (2014). Lippia alba (Verbenaceae): A new tropical autopolyploid complex? American Journal of Botany, 101(6), 1002-1012. https://doi.org/10.3732/ajb.1400149

Reyes-Solano, L., Breksa III, A. P., Valdez-Torres, J. B., Angulo-Escalante, W., & Heredia, J. B. (2017). Chemical composition and antioxidant activity of Lippia alba essential oil obtained by supercritical CO2 and hydrodistillation. African Journal of Biotechnology, 16(17),962-970. https://doi.org/10.5897/AJB2017.15945

Ricciardi, G. A. L., Veglia, J. F., Ricciardi, A. I. A., & Bandoni, A. (1999). Examen comparado de la composición de los aceites esenciales de especies autóctonas de Lippia alba (Mill.) N. E. Br. Universidad Nacional del Nordeste. Comunicaciones científicas y tecnológicas.

Ricciardi, G., Cicció, J. F., Ocampo, R., Lorenzo, D., Ricciardi, A., Bandoni, A., & Dellacassa, E. (2009). Chemical variability of essential oils of Lippia alba (Miller) N. E. Brown growing in Costa Rica and Argentina. Natural Product Communications, 4(6), 853-858. https://doi.org/10.1177/1934578X0900400623

Segleau, J. (2001). Plantas medicinales en el trópico húmedo. Editorial Guayacán.

Sell, C. (2010). Chemistry of essential oils. In K. H. C. Başer & G. Buchbauer (Eds.), Handbook of essential oils: Science, technology and applications. CRC Press, Taylor & Francis.

The Plant List (2013). Verbenaceae. Version 1.1. Published on the Internet. http://www.theplantlist.org/1.1/browse/A/Verbenaceae/

Timóteo, P., Karioti, A., Leitao, S. G., Vincieri, F. F., & Bilia, A. R. (2008). HPLC/DAD/ESI-MS análisis of non-volatile constituents of three Brazilian chemotypes of Lippia alba (Mill.) N. E. Brown. Natural Product Communications, 3(12), 2017-2020.

Topographic Map of Costa Rica. Sandalmelik. (2007, September 16). Costa Rica Topography.png. https://commons.wikimedia.org/wiki/file:Costa_Rica_Topography.png

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. https://doi.org/10.1016/S0021-9673(01)80947-X

von Poser, G. L., Toffoli, M. E., Sobral, M., & Henriques, A. T. (1997). Iridoid glucosides substitution patterns in Verbenaceae and their taxonomic implication. Plant Systematics and Evolution, 205, 265-268. https://doi.org/10.1007/BF01464409

Wharton, P. S., Sundin, C. E., Johnson, D. W., & Kluender, H. C. (1972). Synthesis of dl-hedycaryol. Journal of Organic Chemistry, 37(1), 34-38. https://doi.org/10.1021/jo00966a009

Published

2022-10-07

How to Cite

Chaverri, C., Ramón-Farías, F., & Cicció, J. F. (2022). Chemistry of essential oils of the shrub Lippia alba (Verbenaceae) from Mexico and Costa Rica. UNED Research Journal, 14(2), e4005. https://doi.org/10.22458/urj.v14i2.4005

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