Publicado

2020-05-01

The selective obtaining of amyrins from Amazonian Protium oleoresins

La obtención selectiva de amirinas a partir de oleorresinas de Protium amazónicas

DOI:

https://doi.org/10.15446/rcciquifa.v49n2.89923

Palabras clave:

Protium, alpha and beta-amyrins, yielding extraction, extraction optimization (en)
Protium, amirinas alfa y beta, rendimientos de extracción, optimización de extracción (es)

Autores/as

  • Rosilene Gomes da Silva Ferreira Escola Normal Superior, Universidade do Estado do Amazonas, 3578, Flores, 69050-010, Manaus, Amazonas
  • Fernanda Guilhon-Simplicio Faculdade de Ciências Farmacêuticas, Universidade Federal do Amazonas, Setor Sul, Coroado, 69067-005, Manaus, Amazonas
  • Klenicy Kazumy de Lima Yamaguchi Instituto de Saúde e Biotecnologia, Universidade do Estado do Amazonas, 305, Urucu, 69460-000, Coari, Amazonas
  • Priscila Duarte de Lira Departamento de Química, Instituto de Ciências Exatas, Universidade Federal do Amazonas, Setor Norte, Coroado, 69077-000, Manaus, Amazonas
  • Tallita Marques Machado Faculdade de Ciências Farmacêuticas, Universidade Federal do Amazonas, Setor Sul, Coroado, 69067-005, Manaus, Amazonas
  • Márcio Antônio Couto Ferreira Instituto de Saúde e Biotecnologia, Universidade do Estado do Amazonas, 305, Urucu, 69460-000, Coari, Amazonas
  • Valdir Florêncio da Veiga Júnior Departamento de Engenharia Química, Instituto Militar de Engenharia, 80, Urca, 22290-270, Rio de Janeiro
  • Emerson Silva Lima Faculdade de Ciências Farmacêuticas, Universidade Federal do Amazonas, Setor Sul, Coroado, 69067-005, Manaus, Amazonas

The oleoresin produced by species of genus Protium sp. is rich in alpha and beta-amyrins, two triterpenes with many pharmacogical activities. Considering the need to make the improved obtainment of these products feasible, this study sought to optimize techniques for the extraction and isolation of amyrins from resin. Two methods of extraction (maceration and sonication) with different solvents were compared to direct isolation from crude resin. The isolation of triterpenes was performed by chromatographic columns and the yields of extracts and fractions were analyzed by analysis of variance. The best extraction solvent for amyrins was hexane for both maceration and sonication methods (38.16±2.06% and 37.67±8.21%, respectively). There was no statistical difference between these methods and the direct method (32.05±2.40%). Additionally, the direct method is cheaper and more environmentally friendly. Thus, this study showed that it is possible to obtain a large quantity of amyrins by means of cheap, fast and ecological methods.

La oleorresina producida por especies del género Protium sp. es rica en amirinas alfa y beta, dos triterpenos con muchas actividades farmacológicas. Esta investigación buscó optimizar las técnicas de extracción y aislamiento de amirinas de la resina para hacer factible la obtención mejorada de esos productos. Se compararon dos métodos de extracción (maceración y sonicación) con diferentes solventes con aislamiento directo de la resina cruda. El aislamento de los triterpenos se realizó mediante columnas cromatográficas y los rendimientos de extractos y fracciones fueron hechos mediante análisis de varianza. El mejor solvente para la extracción de amirinas fue el hexano para ambos métodos de maceración y sonicación (38,16±2,06% y 37,67±8,21%, respectivamente). No hubo diferencia estadística entre estos métodos y el método directo (32,05±2,40%). Además, el método directo es más barato y ecológico. De este modo, esta investigación demostró que es posible obtener una gran cantidad de amirinas a través de métodos rápidos, baratos y ecológicos.

Referencias

E.R. da Silva, D.R. Oliveira, P.D. Fernandes, H.R. Bizzo, S.G. Leitão, Ethnopharmacological evaluation of breu essential oils from Protium Species administered by inhalation, J. Evid. Based. Complementary Altern. Med., 2017, ID 2924171 (2017).

E.M. Lima, A.M. Nascimento, D. Lenz, R. Scherer, S.S. Meyrelles, G.A.P. Boëchat, T.U. Andrade, D.C. Endringer, Triterpenes from the Protium heptaphyllum resin – chemical composition and cytotoxicity, Rev. Bras. Farmacogn., 24(4), 399-407 (2014).

H. Lorenzi, Árvores brasileiras: manual de identificação e cultivo de plantas nativas do Brasil, Plantarum, Nova Odessa, 1992, vol. 1.

A.L. Rüdiger, C.C. Silva, V.F. Veiga Júnior, EDXRF Analysis of Amazonian Burseraceae oleoresins, J. Braz. Chem. Soc., 20(6), 1077-1081 (2009).

N.A.J.C. Furtado, L. Pirson, H. Edelberg, L.M. Miranda, C. Loira-Pastoriza, V. Preat, Y. Larondelle, C.M. André, Pentacyclic triterpene bioavailability: an overview of in vitro and in vivo studies, Molecules, 22(3), 400 (2017).

A.L. Rüdiger, A.C. Siani, V.F. Veiga Júnior, The chemistry and pharmacology of the South America genus Protium Burm F (Burseraceae), Pharmacogn. Rev., 1(1), 93-104 (2007).

L. Hernández-Vázquez, S. Mangas, J. Palazón, A. Navarro-Ocaña, Valuable medicinal plants and resins: Commercial phytochemicals with bioactive properties, Ind. Crops Prod., 31(3), 476-480 (2010).

E. Biskup, M. Gołębiowski, R. Gniadecki, P. Stepnowski, E. Łojkowska, Triterpenoid α-amyrin stimulates proliferation of human keratinocytes but does not protect them against UVB damage, Acta Biochim. Pol., 59(2), 255-260 (2012).

R.C.P. Lima-Júnior, D.I.M. Sousa, G.A.C. Brito, C.M. Cunha, M.H. Chaves, V.S.N. Rao, F.A. Santos, Modulation of acute visceral nociception and bladder inflammation by plant triterpene, α,β-amyrin in a mouse model of cystitis: role of tachykinin NK1-receptors, and K+ATP channels, Inflamm. Res., 56, 487-494 (2007).

I. Matos, A.F. Bento, R. Marcon, R.F. Claudino, J.B. Calixto, Preventive and therapeutic oral administration of the pentacyclic triterpene α,β-amyrin ameliorates dextran sulfate sodium-induced colitis in mice: the relevance of cannabinoid system, Mol. Immunol., 54(3-4), 482-492 (2013).

R. Medeiros, M.F. Otuki, M.C.W. Avellar, J.B. Calixto, Mechanisms underlying the inhibitory actions of the pentacyclic triterpene α-amyrin in the mouse skin inflammation induced by phorbol ester 12-O-tetradecanoylphorbol-13-acetate, Eur. J. Pharmacol., 559(2-3), 227-235 (2007).

C.M. Melo, T.C. Morais, A.R. Tomé, G.A.C Brito, M.H. Chaves, V.S Rao, F.A. Santos, Anti-inflammatory effect of α,β-amyrin, a triterpene from Protium heptaphyllum, on cerulein-induced acute pancreatitis in mice, Inflamm. Res., 60(7), 673-681 (2011).

A.O. Nogueira, Y.I.S. Oliveira, B.L. Adjafre, M.E.A. Moraes, G.F. Aragão, Pharmacological effects of the isomeric mixture of alpha and beta amyrin from Protium heptaphyllum: a literature review, Fundam. Clin. Pharmacol., 33(1), 4-12 (2019).

K.K. Okoye, D.L. Ajaghaku, H.N. Okeke, E.E. Ilodigwe, C.S. Nworu, F.B.C. Okoye, Beta-amyrin and alpha-amyrin acetate isolated from the stem bark of Alstonia boonei display profound anti-inflammatory activity, Pharm. Biol., 52(11), 1478-1486 (2014).

M.F. Otuki, F. Vieira-Lima, Â. Malheiros, R.A. Yunes, J.B. Clixto, Topical antiinflammatory effects of the ether extract from Protium kleinii and α-amyrin pentacyclic triterpene, Eur. J. Pharmacol., 507(1-3), 253-259 (2005).

F.A. Santos, J.T. Frota, B.R. Arruda, T.S. de Melo, A.A.C.A da Silva, G.A.C. Brito, M.H. Chaves, V.S. Rao, Antihyperglycemic and hypolipidemic effects of α,β-amyrin, a triterpenoid mixture from Protium heptaphyllum in mice, Lipids Health Dis., 11, 98 (2012).

M. Shih, J. Cherng, Reduction of adhesion molecule production and alteration of eNOS and endothelin-1 mRNA expression in endothelium by Euphorbia hirta L. through its beneficial β-amyrin molecule, Molecules, 19(7), 10534-10545 (2014).

B. Gullón, P. Gullón, T.A. Lú-Chau, M.T. Moreira, J.M. Lema, G. Eibes, Optimization of solvent extraction of antioxidants from Eucalyptus globulus leaves by response surface methodology: characterization and assessment of their bioactive properties, Ind. Crops Prod., 108, 649-659 (2017).

S. Rodríguez-Rojo, A. Visentin, D. Maestri, M.J., Cocero, Assisted extraction of rosemary antioxidantes qith green solvents, J. Food Eng., 109(1), 98-103 (2012).

C.L. Roriz, L. Barros, M.A. Prieto, M.F. Barreiro, P. Morales, I.C.F.R. Ferreira, Modern extraction techniques optimized to extract betacyanins from Gomphrena globosa L., Ind. Crops Prod., 105, 29-40 (2017).

G.F. Aragão, M.C.C. Pinheiro, P.N. Bandeira, T.L.G Lemos, G.S.B. Viana, Analgesic and anti-inflammatory activities of the isomeric mixture of alpha- and beta-amyrin from Protium heptaphyllum (Aubl.) March, J. Herb. Pharmacother., 7(2), 31-47 (2008).

P.N. Bandeira, T.L.G. Lemos, S.M.O. Costa, H.S. dos Santos, Obtenção de derivados da mistura triterpenoídica α- e β-amirina, Rev. Bras. Farmacogn., 17(2), 204-208 (2007).

S.J. Wagh, J.G. Gujar, V.G. Gaikar, Experimental and modeling studies on extraction of amyrins from latex of mandar (Calotropis gigantea), Indian J. Chem. Technol., 19, 427-433 (2012).

K.M.M.B. Carvalho, J.D.B. Marinho Filho, T.S. de Melo, A.J. Araújo, J.D.S. Quetz, M.D.P.S.S. da Cunha, K.M. de Melo, A.A.D.C.A. da Silva, A.R. Tomé, A. Havt, S.G.D.C. Fonseca, G.A.D.C. Brito, M.H. Chaves, V.S. Rao, F.A. Santos, The resin from Protium heptaphyllum prevents high-fat diet-induced obesity in mice: scientific evidence and potential mechanisms, J. Evid. Based Complementary Altern. Med., 2015, 106157 (2015).

G.M. Vieira Júnior, C.M.L. de Souza, M.H. Chaves, Resina de Protium heptaphyllum: isolamento, caracterização estrutural e avaliação das propriedades térmicas, Quim. Nova, 28(2), 183-187 (2005).

X. Guo, A.P. Bruins, T.R. Covey, Characterization of typical chemical background interferences in atmospheric pressure ionization liquid chromatography-mass spectrometry, Rapid. Commun. Mass Spectrom., 20(20), 3145-3150 (2006).

Y. Hayasaka, Analysis of phthalates in wine using liquid chromatography tandem mass spectrometry combined with a hold-back column: Chromatographic strategy to avoid the influence of pre-existing phthalate contamination in a liquid chromatography system, J. Chromatogr. A, 1372, 120-127 (2014).

H. Shen, L. Ying, Y. Cao, G. Pan, L. Zhou, Simultaneous determination of phthalates and parabens in cosmetic products by gas chromatography/mass spectrometry coupled with solid phase extraction (in Chinese), Se Pu, 25(2), 272-275 (2007).

M.O. Dias, L. Hamerski, A.C. Pinto, Separação semipreparativa de α e β-amirina por cromatografia líquida de alta eficiência, Quim. Nova, 34(4), 704-706 (2011).

F.W.A. Barros, P.N. Bandeira, D.J.B. Lima, A.S. Meira, S.S. de Farias, M.R.J.R. Albuquerque, H.S.D. Santos, T.L.G. Lemos, M.O. de Morais, L.V. Costa-Lotufo, C.D.O. Pessoa, Amyrin esters induce cell death by apoptosis in HL-60 leukemia cells, Bioorg. Med. Chem., 19(3), 1268-1276 (2011).

Cómo citar

APA

Gomes da Silva Ferreira, R., Guilhon-Simplicio, F., de Lima Yamaguchi, K. K., Duarte de Lira, P., Marques Machado, T., Couto Ferreira, M. A., da Veiga Júnior, V. F., & Silva Lima, E. (2020). The selective obtaining of amyrins from Amazonian Protium oleoresins. Revista Colombiana de Ciencias Químico-Farmacéuticas, 49(2). https://doi.org/10.15446/rcciquifa.v49n2.89923

ACM

[1]
Gomes da Silva Ferreira, R., Guilhon-Simplicio, F., de Lima Yamaguchi, K.K., Duarte de Lira, P., Marques Machado, T., Couto Ferreira, M.A., da Veiga Júnior, V.F. y Silva Lima, E. 2020. The selective obtaining of amyrins from Amazonian Protium oleoresins. Revista Colombiana de Ciencias Químico-Farmacéuticas. 49, 2 (may 2020). DOI:https://doi.org/10.15446/rcciquifa.v49n2.89923.

ACS

(1)
Gomes da Silva Ferreira, R.; Guilhon-Simplicio, F.; de Lima Yamaguchi, K. K.; Duarte de Lira, P.; Marques Machado, T.; Couto Ferreira, M. A.; da Veiga Júnior, V. F.; Silva Lima, E. The selective obtaining of amyrins from Amazonian Protium oleoresins. Rev. Colomb. Cienc. Quím. Farm. 2020, 49.

ABNT

GOMES DA SILVA FERREIRA, R.; GUILHON-SIMPLICIO, F.; DE LIMA YAMAGUCHI, K. K.; DUARTE DE LIRA, P.; MARQUES MACHADO, T.; COUTO FERREIRA, M. A.; DA VEIGA JÚNIOR, V. F.; SILVA LIMA, E. The selective obtaining of amyrins from Amazonian Protium oleoresins. Revista Colombiana de Ciencias Químico-Farmacéuticas, [S. l.], v. 49, n. 2, 2020. DOI: 10.15446/rcciquifa.v49n2.89923. Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/89923. Acesso em: 22 sep. 2021.

Chicago

Gomes da Silva Ferreira, Rosilene, Fernanda Guilhon-Simplicio, Klenicy Kazumy de Lima Yamaguchi, Priscila Duarte de Lira, Tallita Marques Machado, Márcio Antônio Couto Ferreira, Valdir Florêncio da Veiga Júnior, y Emerson Silva Lima. 2020. «The selective obtaining of amyrins from Amazonian Protium oleoresins». Revista Colombiana de Ciencias Químico-Farmacéuticas 49 (2). https://doi.org/10.15446/rcciquifa.v49n2.89923.

Harvard

Gomes da Silva Ferreira, R., Guilhon-Simplicio, F., de Lima Yamaguchi, K. K., Duarte de Lira, P., Marques Machado, T., Couto Ferreira, M. A., da Veiga Júnior, V. F. y Silva Lima, E. (2020) «The selective obtaining of amyrins from Amazonian Protium oleoresins», Revista Colombiana de Ciencias Químico-Farmacéuticas, 49(2). doi: 10.15446/rcciquifa.v49n2.89923.

IEEE

[1]
R. Gomes da Silva Ferreira, «The selective obtaining of amyrins from Amazonian Protium oleoresins», Rev. Colomb. Cienc. Quím. Farm., vol. 49, n.º 2, may 2020.

MLA

Gomes da Silva Ferreira, R., F. Guilhon-Simplicio, K. K. de Lima Yamaguchi, P. Duarte de Lira, T. Marques Machado, M. A. Couto Ferreira, V. F. da Veiga Júnior, y E. Silva Lima. «The selective obtaining of amyrins from Amazonian Protium oleoresins». Revista Colombiana de Ciencias Químico-Farmacéuticas, vol. 49, n.º 2, mayo de 2020, doi:10.15446/rcciquifa.v49n2.89923.

Turabian

Gomes da Silva Ferreira, Rosilene, Fernanda Guilhon-Simplicio, Klenicy Kazumy de Lima Yamaguchi, Priscila Duarte de Lira, Tallita Marques Machado, Márcio Antônio Couto Ferreira, Valdir Florêncio da Veiga Júnior, y Emerson Silva Lima. «The selective obtaining of amyrins from Amazonian Protium oleoresins». Revista Colombiana de Ciencias Químico-Farmacéuticas 49, no. 2 (mayo 1, 2020). Accedido septiembre 22, 2021. https://revistas.unal.edu.co/index.php/rccquifa/article/view/89923.

Vancouver

1.
Gomes da Silva Ferreira R, Guilhon-Simplicio F, de Lima Yamaguchi KK, Duarte de Lira P, Marques Machado T, Couto Ferreira MA, da Veiga Júnior VF, Silva Lima E. The selective obtaining of amyrins from Amazonian Protium oleoresins. Rev. Colomb. Cienc. Quím. Farm. [Internet]. 1 de mayo de 2020 [citado 22 de septiembre de 2021];49(2). Disponible en: https://revistas.unal.edu.co/index.php/rccquifa/article/view/89923

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