Chemical profile of essential oils of the Costa Rican native tree Myrcianthes storkii (Myrtaceae)

Chemical profile of essential oils of the Costa Rican native tree Myrcianthes storkii (Myrtaceae)

Authors

DOI:

https://doi.org/10.22458/urj.v16i1.4863

Keywords:

Myrcianthes storkii, essential oils, cis-calamenene, myrcene, α-pinene, 1,8-cineole

Abstract

Introduction: The genus Myrcianthes ranges from southern Florida to Chile, including the Caribbean, and the species Myrcianthes storkii is a shrub or tree found in Costa Rica and western Panama, in wet to very rainy, cloud, and oak forests (altitude 1300-3150m). Objective: To identify the chemical composition of essential oils from leaves, floral buds, and twigs of M. storkii of Costa Rica. Methods: We obtained the essential oils through hydrodistillation in a Clevenger-type apparatus. The chemical composition of the oils was done by GC/FID and GC/MS, using the retention indices on DB-5 and Carbowax types of capillary columns in addition to mass spectra.  Results: The oils consisted mainly of terpenoids (55,45-87,75%). A total of 281 compounds accounted for 91,27-74,56% of the total amount of oils. The major constituents from the leaf oil were myrcene (17,44%), cis-calamenene (12,60%), α-pinene (5,48%), (E)-caryophyllene (5,16%), limonene (3,91%), p-cymene (3,71%), 1,8-cineole (2,80%), and α-humulene (2,80%). The floral bud essential oil consisted mainly of α-pinene (15,23%), cis-calamenene (12,70%), myrcene (8,59%), 1,8-cineole (4,26%), germacrene B (3,65%), α-humulene (3,55%), and (E)-caryophyllene oxide (2,93%). The major components of twig oil were cis-calamenene (11,31%), palmitic acid (7,99%), (E)-caryophyllene (4,68%), -cadinene (3,28%), cubenol (3,24%), and (Z)-caryophyllene oxide (2,94%). Conclusion: The presence of a significant quantity of myrcene and cis-calamenene seems to be characteristic of this species.

References

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

Anaya, A. L., Espinosa-García, F., Cruz-Ortega, R. (Eds.). (2001). Relaciones químicas entre organismos: aspectos básicos y perspectivas de su aplicación. Plaza y Valdés México.

Apel, M. A., Sobral, M., & Henriques, A. T. (2006). Composição química do oleo volatile de Myrcianthes nativas da região sul do Brasil. Revista Brasileira de Farmacognosia, 16(3), 402-407. https://doi.org/10.1590/S0102-695X2006000300019

Araujo, L., Rondón, M., Morillo, A., Páes, E., & Rojas-Fermín, L. (2017). Antimicrobial activity of the essential oil of Myrcianthes myrcinoides (Kunth) Grifo (Myrtaceae) collected in the Venezuelan Andes. PharmacologyOnLine, 2, 200-204. https://tinyurl.com/ynnzyf83

Armijos, C., Valarezo, E., Cartuche, L., Zaragoza, T., Finzi, P. V., Mellerio, G. G., & Vidari, G. (2018). Chemical composition and antimicrobial activity of Myrcianthes fragrans essential oil, a natural aromatizer of the traditional Ecuadorian beverage colada morada. Journal of Ethnopharmacology, 225, 319-326. https://doi.org/10.1016/j.jep.2018.07.018

Barrie, F. R. (2007). Myrtaceae. In B. E. Hammel, M. H. Grayum, C. Herrera, & N. Zamora (Eds.). Manual de Plantas de Costa Rica. Vol. 6. (pp. 728-784). Missouri Botanical Garden Press.

Behr, A., & Johnen, L. (2009). Myrcene as a natural base chemical in sustainable chemistry: a critical review. ChemSusChem: Chemistry-Sustainability-Energy-Materials, 2(12), 1072-1095.

Boncan, D. A. T., Tsang, S. S. K., Li, C., Lee, I. H. T., Lam, H.-M., Chan, T.-F., & Hui, J. H. L. (2020). Terpenes and terpenoids in plants: Interactions with environment and insects. International Journal of Molecular Sciences, 21(19), 7382. https://doi.org/10.3390/ijms21197382

Carmen, P., De La Torre, C., & Retamar, J. A. (1972). Essential oil of Myrcianthes callicoma. Essenze e Derivati Agrumari, 42, 429-432.

Chaverri, C., & Cicció, J. F. (2017). Essential oil from leaves of Myrcianthes fragrans (Myrtaceae) from Costa Rica. A new chemotype? Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, 16(4), 385-397. https://www.redalyc.org/pdf/856/85651256004.pdf

Cole, R. A., Haber, W. A., Lawton, R. O., & Setzer, W. N. (2008). Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica. Chemistry and Biodiversity, 5(7), 1327-1334. https://doi.org/10.1002/cbdv.200890120

Collin, G., Garneau, F.-X., Gagnon, H., Pichette, A., & Lavoie, S. (2010). Analysis of cymenes in essential oils: the case of Lepechinia meyeni (Walp.) Epling. Journal of Essential Oil Research, 22(4), 310-313. https://doi.org/10.1080/10412905.2010.9700333

de Jesús, R. A., de Oliveira, H. L. M., Bortolucci, W. de C., Campo, C. F. de A. A., Faria, M. G. I., Goncalves, J. E., Colauto, N. B., Gazim, Z. C. & Linde, G. A. (2021). Antioxidant and antibacterial activity of Myrcianthes pungens leaf essential oil. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, 20(2), 147-161. https://doi.org/10.37360/blacpma.21.20.2.12

Demo, M. S., Oliva, M. M., Zunino, M. P., López, M. L., & Zygadlo, J. A. (2002). Aromatic plants from Yungas. Part IV: Composition and antimicrobial activity of Myrcianthes pseudo-mato essential oil. Pharmaceutical Biology, 40(7), 481-484. https://doi.org/10.1076/phbi.40.7.481.14689

Escobar-Bravo, R., Lin, P-A., Waterman, J. M., & Erb, M. (2023). Dynamic environmental interactions shaped by vegetative plant volatiles. Natural Product Reports, 40, 840-865. https://doi.org/10.1039/d2np00061j

Gershenzon, J., & Dudareva, N. (2007). The function of terpene natural products in the natural world. Nature Chemical Biology, 3(7), 408-414. https://doi.org/10.1038/nchembio.2007.5

Granados, C., Yáñez, X., & Acevedo, D. (2014). Evaluación de la actividad antioxidante del aceite esencial foliar de Myrcianthes leucoxyla de norte de Santander (Colombia). Información Tecnológica, 25(3), 11-16. https://doi.org/10.4067/S0718-07642014000300003

Kim, Y-K., Cool, L. G., & Zavarin, E. cis-Calamenene-related sesquiterpenoids from Cupressus bakeri foliage. Phytochemistry, 36(4), 961-965.

Lee, J.-H., Lee, K., Lee, D.H., Shin, S. Y., Yong, Y., & Lee, Y. H. (2015). Anti-invasive effect of β-myrcene, a component of the essential oil from Pinus koraiensis cones, in metastatic MDA-MB-231 human breast cancer cells. Journal of the Korean Society for Applied Biological Chemistry, 58(4), 563-569. https://doi.org/10.1007/s13765-015-0081-3

Lopez, J. B., Jean, F. I., Gagnon, H., Collin, G., Garneau, F.X., & Pichette, A. (2005). Essential Oils from Bolivia. VII. Myrtaceae: Myrcianthes osteomeloides (Rusby) McVaugh and Myrcianthes pseudomato (Legrand) McVaugh. Journal of Essential Oil Research, 17(1), 64-65. https://doi.org/10.1080/10412905.2005.9698832

Lorenzo, D., Dellacassa, E., Bonaccorsi, I., & Mondello, L. (2001). Uruguayan essential oils. Composition of leaf oil of Myrcianthes cisplatensis (Camb.) Berg. ("Guayabo colorado") (Myrtaceae). Flavour and Fragrance Journal, 16(2), 97-99. https://doi.org/10.1002/1099-1026(200103/04)16:2<97::AID-FFJ952>3.0.CO;2-C

Malagón, O., Vila, R., Iglesias, J., Zaragoza, T., & Cañigueral, S. (2003). Composition of the essential oils of four medicinal plants from Ecuador. Flavour and Fragrance Journal, 18(6), 527-531. https://doi.org/10.1002/ffj.1262

Marin, R., Apel, M. A., Limberger, R. P., Raseira, M. C. B., Pereira, J. F. M., Zuanazzi, J. A. S., & Henriques, A. T. (2008). Volatile components and antioxidant activity from some myrtaceous fruits cultivated in Southern Brazil. Latin American Journal of Pharmacy, 27(2), 172-177. https://tinyurl.com/yo24maef

McVaugh, R. (1963). Tropical American Myrtaceae, II. Notes on generic concepts and descritions of previously unrecognized species. Fieldiana Botany, 29(8), 395-532. https://www.biodiversitylibrary.org/item/19982#page/111/mode/1up

Montalván, M., Peñafiel, M. A., Ramírez, J., Cumbicus, N., Bec, N., Larroque, C., Bicchi, C., & Gilardoni, G. (2019). Chemical composition, enantiomeric distribution, and sensory evaluation of the essential oils distilled from the Ecuadorian species Myrcianthes myrcinoides (Kunth) Grifo and Myrcia mollis (Kunth) DC. (Myrtaceae). Plants, 8, 511. https://doi.org/10.3390/plants8110511

Mora, V. F. D., Rojas, L. B., Usubillaga, A., Carmona, J., & Silva, B. (2009). Composición química del aceite esencial de Myrcianthes fragrans (Sw.) McVaugh de los Andes venezolanos. Revista de la Facultad de Farmacia, 51(1), 20-23.

Pianaro, A., Menezes, C., Kerr, W. E., Singer, R. B., Patricio, E. F., Marsaioli, A. J. (2009). Stingless bees: Chemical differences and potential functions in Nannotrigona testaceicornis and Plebeia droryana males and workers. Journal of Chemical Ecology, 35, 1117-1128. https://doi.org/10.1007/s10886-009-9679-4

Pino, J. A., Rosado, A., Bello, A., Urquiola, A., & García, G. (2000). Essential oil of Myrcianthes fragrans (Sw.) McVaugh from Cuba. Journal of Essential Oil Research, 12(2), 225-226. https://doi.org/10.1080/10412905.2000.9699503

Pombo, L. M., Borrego, P., Matulevich, J. Teheran, A. A., & Barajas, L. (2016). Composition and antimicrobial activity of the essential oils of three plant species from the Sabana of Bogotá (Colombia): Myrcianthes leucoxyla, Vallea stipularis and Phyllanthus salviifolius. Natural Products Communications, 11(12), 1913-1918. https://doi.org/10.1177/1934578X1601101234

Quijano-Célis, C., Pino, J. A., Echeverri, D., & Morales, G. (2016). Essential oil of Myrcianthes leucoxyla (Ortega) McVaugh leaves from Colombia. Journal of Essential Oil Bearing Plants, 19(6), 1510-1515. https://doi.org/10.1080/0972060X.2016.1224687

Rafii, Z., Cool, L. G., & Zavarin, E. (1992). Variability of foliar mono- and sesquiterpenoids of Cupressus bakeri. Biochemical Systematics and Ecology, 20(2), 123-131.

Rao, V. S., Menezes, A. M., & Viana, G. S. (1990). Effect of myrcene on nociception in mice. Journal of Pharmacy and Pharmacology, 42(12), 877-878. https://doi.org/10.1111/j.2042-7158.1990.tb07046.x

Romanenko, E. P. & Tkachev, A. V. (2006). Identification by GC-MS of cymene isomers and 3,7,7-trimethylcyclohepta-1,3,5-triene in essential oils. Chemistry of Natural Compounds, 42(6), 699-701. https://doi.org/10.1007/s10600-006-0256-6

Romero, D., Cartuche, L., Valarezo, E., Cumbicus, N., & Morocho, V. (2023). Chemical profiling, anticholinesterase, antioxidant, and antibacterial potential of the essential oil from Myrcianthes discolor (Kunth) McVaugh, an aromatic tree from Southern Ecuador. Antibiotics, 12(4), 677. https://doi.org/10.3390/antibiotics12040677

Rufino, A. T., Ribeiro, M., Sousa, C., Judas, F., Salgueiro, L., Cavaleiro, C., & Mendes, A. F. (2015). Evaluation of the anti-inflammatory, anti-catabolic and pro-anabolic effects of E-caryophyllene, myrcene and limonene in a cell model of osteoarthritis. European Journal of Pharmacology, 750, 141-150. https://doi.org/10.1016/j.ejphar.2015.01.018

Setzer, W. N., Setzer, M. C., Moriarity, D. M., Bates, R. B., & Haber, W. A. (1999). Biological activity of the essential oil of Myrcianthes sp. nov. “Black Fruit” from Monteverde, Costa Rica. Planta Medica, 65(5), 468-469. https://doi.org/10.1055/s-2006-960816

Silva, D. A., Matulevich, J. A., & Devia, B. O. (2016). Composición química del aceite esencial de hojas de Myrcianthes rhopaloides (Kunt) McVaugh (Myrtaceae). Revista Facultad de Ciencias Básicas, 12(1), 84-91. https://doi.org/10.18359/rfcb.1857

Surendran, S., Qassadi, F., Surendran, G., Lilley, D., & Heinrich, M. (2021). Myrcene - What are the potential health benefits of this flavouring and aroma agent? Frontiers in Nutrition, 8, 699666. https://doi.org/10.3389/fnut.2021.699666

Taher, H. A., Santi de Bongioanni, M. N., & Talenti, E. C. J. (1983). Study of the essential oil of Myrcianthes cisplatensis (Cambassedes) Berg. Essenze e Derivati Agrumari , 53, 13-25.

Toloza, A. C., Zygadlo, J., Cueto, G. M., Biurrun, F., Zerba, E., & Picollo. M. I. (2006). Fumigant and repellent properties of essential oils and component compounds against permethrin-resistant Pediculus humanus capitis (Anoplura: Pediculidae) from Argentina. Journal of Medical Entomology, 43(5), 889-895. https://doi.org/10.1093/jmedent/43.5.889

Tucker, A. O., Maciarello, M. J., & Landrum, L. R. (1992). Volatile leaf oils of Caribbean Myrtaceae. VI. Myrcianthes fragrans (Sw.) McVaugh of Jamaica. Journal of Essential Oil Research, 4(3), 313-314. https://doi.org/10.1080/10412905.1992.9698071

Tucker, A. O., Maciarello, M. J., & Landrum, L. R. (2002). Volatile leaf oil of Myrcianthes coquimbensis (Barnéoud) Landrum et Grifo (Myrtaceae) of Chile. Journal of Essential Oil Research, 14(1), 40-41. https://doi.org/10.1080/10412905.2002.9699756

Ubiergo, G., Taher, H. A., & Talenti, E. C. (1986). Mono and sesquiterpenoids from the essential oil of Myrcianthes pungens. Anales de la Asociación Química Argentina, 74, 567-569.

van den Dool, H., & Kratz, P. D. (1963). A generalization of the retention index 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

Vasconcelos, T. N. C., Proença, C. E. B., Ahmad, B., Aguilar, D. S., Aguilar, R., Amorim, B. S., Campbell, K., Costa, I. R., De-Carvalho, P. S., Faria, J. E. Q., Giaretta, A., Kooij, P. W., Lima, D. F., Mazine, F. F., Peguero, B., Prenner, G., Santos, M. F., Soewarto, J., Wingler, A., & Lucas, E. J. (2017). Myrteae phylogeny, calibration, biogeography and diversification patterns: Increased understanding in the most species rich tribe of Myrtaceae. Molecular Phylogenetics and Evolution, 109, 113-137. https://doi.org/10.1016/j.ympev.2017.01.002

Wallace, W. E. (2021). Mass spectra (by NIST Mass Spec Data Center). In P.J. Linstrom & W.G. Mallard (Eds.), Nits Chemistry WebBook: NIST Standard Reference Database Number 69. National Institute of Standards and Technology. http://webbook.nist.gov

Werka, J. S., Boehme, A. K., & Setzer, W. N. (2007). Biological activities of essential oils from Monteverde, Costa Rica. Natural Product Communications, 2(12), 1215-1219. https://doi.org/10.1177/1934578X0700201204

Weyerstahl, P., Christiansen, C., & Marschall, H. (1996). Constituents of Brazilian vassoura oil. Flavour and Fragrance Journal, 11(1), 15-23. https://doi.org/10.1002/(SICI)1099-1026(199601)11:1%3C15::AID-FFJ541%3E3.0.CO;2-H

World Flora Online (WFO). (2023). Myrcianthes O. Berg. https://tinyurl.com/yogu523b

Wilson, P. G. (2011). Myrtaceae. In Kubitzki, K. (ed.). Families and genera of vascular plants. Vol. 10. Flowering plants: Eudicots-Sapindales, Cucurbitales, Myrtaceae. Springer-Verlag.

Xanthis, V., Fitsiou, E., Voulgaridou, G. P., Bogadakis, A., Chlichlia, K., Galanis, A., & Pappa, A. (2021). Antioxidant and cytoprotective potential of the essential oil Pistacia lentiscus var. chia and its major components myrcene and α-pinene. Antioxidants, 10, 127. https://doi.org/10.3390/antiox10010127

Yáñez, X., Granados, C., Durán, M. (2013). Composición química y actividad antibacteriana del aceite esencial de Myrcianthes leucoxyla de Pamplona (Colombia). @limentech Ciencia y Tecnología Alimentaria, 11(1), 79-84. https://doi.org/10.240/16927125.v1.n1.2013.497

Yazaki, K., Arimura, G-I., Ohnishi, T. (2017). ’Hidden’ terpenoids in plants: Their biosynthesis, location and ecological roles. Plant Cell Physiology, 58(10), 1615-1621. https://doi.org/10.1093/pcp/pcx123

Zygadlo, J. A., Rotman, A. D., Perez-Alonso, M. J., & Velasco-Negueruela, A. (1997). Leaf oils of two Myrcianthes species from Argentina: M. pungens (Berg.) Legrand and M. cisplatensis (Camb.) Berg. Journal of Essential Oil Research, 9(2), 237-239. https://doi.org/10.1080/10412905.1997.9699470

Published

2024-01-25

How to Cite

Chaverri, C., & Cicció, J. F. (2024). Chemical profile of essential oils of the Costa Rican native tree Myrcianthes storkii (Myrtaceae). UNED Research Journal, 16(1), e4863. https://doi.org/10.22458/urj.v16i1.4863

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