Effects of Acmella oleracea methanolic extract and fractions on the tyrosinase enzyme

Abstract

The aim of the current study is to evaluate the effect of Acmella olerácea (L.) R.K. Jansen, Asteraceae, methanolic extract, hexane (84.28% spilanthol) and dichloromethane (approximately 100% spilanthol) fractions on the tyrosinase enzyme. The dehydrated jambu extract was obtained through maceration using methanol. The extract residue was solubilized in MeOH/H2O (8:2) and subjected to liq.-liq. partition in organic solvents. Both the extraction and the partition procedures were conducted with three replicates. The analyses were performed using GC-MS, 1H and 13C NMR. The hexane fraction provided samples containing 84.28,82.91 and 62.83% spilanthol in repetitions 1,2 and 3, respectively. The dichloromethane fraction showed 88.55% spilanthol in repetition 1, and approximately 100% spilanthol in repetitions 2 and 3. The jambu extract as well as the hexane fraction (84.28% spilanthol) were able to activate the oxidizing activity of the tyrosinase enzyme for L-DOPA. The dichloromethane fraction (approximately 100% spilanthol) showed stronger inhibition effect on the tyrosinase enzyme in the first 10 min. The results raise the interest in study in spilanthol formulations for topical use, since it may prevent and/or slow skin hyperpigmentation or depigmentation processes. Furthermore, spilanthol may be used to control the enzymatic browning in fruits and vegetables.

References

  1. Boonen, J., Baert, B., Burvenich, C., Blondeel, P., de Saeget, S., de Spiegeleer, B., 2010a. LC-MS profiling of JV-alkylamides in Spilanthes armella extract and the transmucosal behavior of is main bioactive spilanthol. J. Pharm Biomed. 53, 243–249.

    CAS  Article  Google Scholar 

  2. Boonen, J., Baert, B., Roche, N., Burvenich, C., de Spiegeleer, B., 2010b. Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilantes acmella (Compositae) extracts. J Ethnopharmacol. 127, 77–84.

    CAS  Article  PubMed  Google Scholar 

  3. Borges, L.da.S., Vieira, MAR., Marques, M.O.M., Vianello, F., Lima, G.P.P., 2012. Influence of organic and mineral soil fertilization on essential oil of Spilanthes oleracea cv. jambuarana. Am. J. Plant Physiol. 7, 135–142.

    CAS  Article  Google Scholar 

  4. Castro, K.N.C., Lima, D.F., Vasconcelos, L.C., Leite, J.R.S.A., Santos, R.C., Neto, A.A.P., Costa-Júnior, L.M., 2014. Acaricide activity in vitro of Acmella oleracea against Rhipicephalus microplus. Parasitol. Res. 113, 3697–3701.

    CAS  Article  PubMed  Google Scholar 

  5. Chang, T.S., 2009. An updated review of tyrosinase inhibitors. Int. J. Mol Sci. 10, 2440–2475.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  6. Chang, T.S., 2012. Natural melanogenesis inhibitors acting through the down-regulation of tyrosinase activity. Materials 5, 1661–1685.

    CAS  Article  PubMed Central  Google Scholar 

  7. Demarne, F., Passaro, G. 2005. Use of an Acmella oleracea extract for the botulinum toxin-like effect thereof in an anti-wrinkle cosmetic composition. US Patent No. 7,531,193B2.

    Google Scholar 

  8. Dias, A.M.A., Santos, P., Seabra, I.J., Junior, R.N.C., Braga, M.E.M., Sousa, H.C.de, 2012. Spilanthol from Spilanthes acmella flowers, leaves and stems obtained by selective supercritical carbon dioxide extraction. J. Supercrit. Fluids 61, 62–70.

    CAS  Article  Google Scholar 

  9. Figueiredo, L.C., 2003. Câncer de pele: estudos nos principais marcadores moleculares do melanoma cutâneo. Rev. Bras. Cancerol. 49, 179–183.

    Google Scholar 

  10. Karim, A.A., Azlan, A., Ismail, A., Hashim, P., Gani, S.S.A., Zainudin, B.H., Abdullah, NA, 2014. Phenolic composition, antioxidant, anti-wrinkles and tyrosinase inhibitory activities of cocoa pod extract. BMC Complement. Altera Med. 14, 381.

    Article  Google Scholar 

  11. Karioti, A., Protopappa, A., Megoulas, N., Skaltsa, H., 2007. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorg. Med. Chem. 15, 2708–2714.

    CAS  Article  PubMed  Google Scholar 

  12. Khan, K.M., Mughal, U.R., Khan, M.T.H., Ullah, Z., Perveenb, S., Choudhary, M.I., 2006. Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg. Med Chem. 14, 6027–6033.

    CAS  Article  PubMed  Google Scholar 

  13. Ley, J.P., Krammer, G., Looft, J., Reinders, G., Bertram, H., 2006. Structure-activity relationships oftrigeminal effects for artificial and naturally occurring alkamides related to spilanthol. Dev. Food Sci. 43, 21–24.

    CAS  Article  Google Scholar 

  14. Lim, T.Y., Lim, Y.Y., Yule, CM., 2009. Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four macaranga species. Food Chem. 114, 594–599.

    CAS  Article  Google Scholar 

  15. Mbeunkui, F., Grace, M.H., Lategan, C., Smith, P.J., Raskin, I., Lila, M.A., 2011. Isolation and identification of antiplasmodial JV-alkylamides from Spilanthes acmella flowers using centrifugal partition chromatography and ESI-IT-TOF-MS. J. Chro-matogr. B 879, 1886–1892.

    CAS  Article  Google Scholar 

  16. Miot, L.D.B., Miot, H.A., da Silva, M.G., Marques, M.E.A., 2009. Fisiopatologia do melasma. An. Bras Dermatol. 84, 623–635.

    Article  PubMed  Google Scholar 

  17. Molina-Torres, J., Salazar-Cabrera, C.J., Armenta-Salinas, C., Ramírez-Sánchez, E., 2004. Fungistatic and bacteriostatic activities of alkamides from Heliopsis longipes roots: affinin and reduces amides. J. Agric. Food Chem. 52, 4700–4704.

    CAS  Article  PubMed  Google Scholar 

  18. Molina-Torres, J., Salgado-Garciglia, R., Ramirez-Chanez, E., del Rio, R.E., 1996. Purely oleflnic alkamides in Heliopsis longipes and Acmella (Spilanthes) oppositifolia. Biochem. Syst. Ecol. 24, 43–47.

    CAS  Article  Google Scholar 

  19. Nakatani, N., Nagashima, M., 1992. Pungent alkamides from Spilanthes acmella L. var. oleracea Clarke. Biosci. Biotechnol. Biochem. 56, 759–762.

    CAS  Article  PubMed  Google Scholar 

  20. Nascimento, A.M., de Souza, L.M., Baggio, C.H., de P. Werner, M.F., Maria-Ferreira, D., da Silva, L.M., Sassaki, G.L., Gorin, P.A.J., Iacomini, M., Cipriani, T.R., 2013. Gastroprotective effect and structure of a rhamnogalacturonan from Acmella oleracea. Phytochemistry 85, 137–142.

    CAS  Article  PubMed  Google Scholar 

  21. Okunji, C., Komarnytsky, S., Fear, G., Poulev, A., Ribnicky, D.M., Awachie, P.I., Ito, Y., Raskin, I., 2007. Preparative isolation and identification of tyrosinase inhibitors from the seeds of Garcinia kola by high-speed counter-current chromatography. J. Chromatogr. A 1151, 45–50.

    CAS  Article  PubMed  Google Scholar 

  22. Oliveira, A., Amaral, A.J., Andrade, J., Nascimento, V., Mendes, K., Reis, J., 2011. Desenvolvendo construções de apriscos na agricultura familiar. Cad Agroecol. 6, 1–4.

    Google Scholar 

  23. Patil, S.S., Zucker, M., 1965. Potato phenolases. J. Biol Chem. 240, 3938–3943.

    CAS  PubMed  Google Scholar 

  24. Ramsewak, R.S., Erickson, A.J., Nair, M.G., 1999. Bioactive N-isobutylamides fromthe flower buds of Spilanthes Acmella. Phytochemistry 51, 729–732.

    CAS  Article  PubMed  Google Scholar 

  25. Ratnasooriya, W.D., Pieris, K.P.P., Samaratunga, U., Jayakody, J.R.A.C., 2004. Diuretic activity of Spilanthes acmella flowers in rats. J Ethnopharmacol. 91, 317–320.

    CAS  Article  PubMed  Google Scholar 

  26. Rebelio, F.K., Homma, A.K., 2005. O uso da terra na Amazônia: uma proposta para reduzir desmatamentos e queimadas. Amazônia. Ciene Desenv. 1, 199–236.

    Google Scholar 

  27. Rios, M.Y., Aguilar-Guadarrama, A.B., Gutierrez, M.D., 2007. Analgesic activity of affinin, an alkamide from Heliopsis longipes (Compositae). J. Ethnopharmacol. 110, 364–367.

    CAS  Article  PubMed  Google Scholar 

  28. Rojas, J.J., Ochoa, V.J., Ocampo, S.A., Muñoz, J.F., 2006. Screening for antimicrobial activity often medicinal plants used in Colombian folkloric medicine: a possible alternative in the treatment of non-nosocomial infections. BMC Complement. Altern Med. 6, 2–7.

    Article  PubMed  PubMed Central  Google Scholar 

  29. Seo, S.Y., Sharma, V.K., Sharma, N., 2003. Mushroom tytosinase: recent prospects. J. Agric. Food Chem. 51, 2837–2853.

    CAS  Article  PubMed  Google Scholar 

  30. Sharma, V., Boonen, J., Chauhan, N.S., Thakur, M., de Spiegeleer, B., Dixit, V.K., 2011. Spilanthes acmella ethanolic flower extract: LC-MS alkylamide profiling and its effects on sexual behavior in male rats. Phytomedicine 18, 1161–1168.

    CAS  Article  PubMed  Google Scholar 

  31. Spencer, R.P., Valentine, R.J., Field, J.B., 1956. Tyrosinase substrates and inhibitors studied colorimetrically. Acta Pharmacol, toxicol. 12, 196–199.

    CAS  Article  Google Scholar 

  32. Spiegeleer, B., Boonen, J., Malysheva, S.V., Mavungu, J.D., de Saeger, S., Roche, N., Blondeel, P., Taevernier, L., Veryser, L., 2013. Skin penetration enhancing properties of the plant JV-alkylamide spilanthol. J Ethnopharmacol. 148, 117–125.

    Article  PubMed  Google Scholar 

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Acknowledgements

The authors are grateful to FAPERJ, CNPq, and to CAPES for granting the scholarships and the financial support.

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AFB, KCS, MCCO, MGC, and AUOSR all contributed to the writing of this article. AFB, MGC, and AUOSR obtained and identified samples. KCS and MCCO performed enzymatic analyzes.

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Correspondence to Alan F. Barbosa.

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Barbosa, A.F., Silva, K.C.B., de Oliveira, M.C.C. et al. Effects of Acmella oleracea methanolic extract and fractions on the tyrosinase enzyme. Rev. Bras. Farmacogn. 26, 321–325 (2016). https://doi.org/10.1016/j.bjp.2016.01.004

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Keywords

  • Jambu
  • Acmella oleracea
  • Spilanthol
  • Tyrosinase