Skip to main content
SpringerLink
Log in

Influence of Supercritical CO2 Extraction on Fatty Acids Profile, Volatile Compounds and Bioactivities from Rosmarinus officinalis

  • Original Paper
  • Published:
Waste and Biomass Valorization Aims and scope Submit manuscript

Abstract

Rosemary oil was extracted by supercritical carbon dioxide (CO2) as a solvent. The parameters of pressure, temperature, and ethanol as co-solvent were evaluated through a Taguchi experimental design. Extraction yield of rosemary oil increased with high pressure (350 bar) and mid-range temperature (40 °C), while the addition of ethanol as co-solvent did not improve the extraction yield. Palmitic, α-linolenic, linoleic, oleic, and stearic acid were the main fatty acids detected (3.96% w/w) in the extracted oil. The major volatile compounds found in the oil (75.74% w/w) included d-camphor, eicosane, 1,8-cineole, tetracosane, borneol, and β-caryophyllene. The extracted oils showed antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans, while Escherichia coli was less sensitive to inhibition. Antioxidant activities on DPPH and TEAC assays were higher at 60 °C, 100 bar without ethanol, while antioxidant activity on FRAP assay was improved at 40 °C, 100 bar, and ethanol as co-solvent. Operational conditions used in the present extraction process (a variation in temperature, pressure, and co-solvent) are described.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Arranz, E., Jaime, L., García-Risco, M.R., Fornari, T., Reglero, G., Santoyo, S.: Anti-inflammatory activity of rosemary extracts obtained by supercritical carbon dioxide enriched in carnosic acid and carnosol. Int. J. Food Sci. Technol. 50, 674–681 (2015)

    Google Scholar 

  2. Babovic, N., Djilas, S., Jadranin, M., Vajs, V., Ivanovic, J., Petrovic, S., Zizovic, I.: Supercritical carbon dioxide extraction of antioxidant fractions from selected Lamiaceae herbs and their antioxidant capacity. Inn. Food Sci. Emerg. Technol. 11, 98–107 (2010)

    Google Scholar 

  3. Bajalan, I., Rouzbahani, R., Pirbalouti, A.G., Maggi, F.: Antioxidant and antibacterial activities of the essential oils obtained from seven Iranian populations of Rosmarinus officinalis. Ind. Crops Prod. 107, 305–311 (2017)

    Google Scholar 

  4. Balouiri, M., Sadiki, M., Ibnsouda, S.K.: Methods for in vitro evaluating antimicrobial activity: a review. J. Pharma. Anal. 6, 71–79 (2016)

    Google Scholar 

  5. Bendif, H., Miara, M.D., Kalboussi, Z., Grauzdytė, D., Povilaitis, D., Venskutonis, P.R., Maggi, F.: Supercritical CO2 extraction of Rosmarinus eriocalyx growing in Algeria: chemical composition and antioxidant activity of extracts and their solid plant materials. Ind. Crops Prod. 111, 768–774 (2018)

    Google Scholar 

  6. Benzie, I.F.F., Strain, J.J.: The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal. Biochem. 239, 70–76 (1996)

    Google Scholar 

  7. Bicchi, C., Binello, A., Rubiolo, P.: Determination of phenolic diterpene antioxidants in rosemary (Rosmarinus officinalis L.) with different methods of extraction and analysis. Phytochem. Anal. 11, 236–242 (2000)

    Google Scholar 

  8. Bittencourt Dutra de Sousa, E.M., Toussaint, V.A., Shariati, A., Florusse, L.J., Chiavone-Filho, O., Meireles, M.A.A., Peters, C.J.: Phase behavior of systems consisting of supercritical carbon dioxide and eucalyptus or rosemary essential oil. Fluid Phase Equil. 428, 32–37 (2016)

    Google Scholar 

  9. Brand-Williams, W., Cuvelier, M.E., Berset, C.: Use of a free radical method to evaluate antioxidant activity. LWT Food Sci. Technol. 28, 25–30 (1995)

    Google Scholar 

  10. Carissimi, G., Montalbán, M.G., Díaz Baños, F.G., Víllora, G.: High pressure phase equilibria for binary mixtures of CO2 + 2-pentanol, vinyl butyrate, 2-pentyl butyrate or butyric acid systems. J. Supercrit. Fluids 135, 69–77 (2018)

    Google Scholar 

  11. Chen, H.-H., Chung, C.-C., Wang, H.-Y., Huang, T.-C.: Application of Taguchi method to optimize extracted ginger oil in different drying conditions. IPCBEE 9, 310–316 (2011)

    Google Scholar 

  12. Conde-Hernández, L.A., Espinosa-Victoria, J.R., Trejo, A., Guerrero-Beltrán, J.: CO2-supercritical extraction, hydrodistillation and steam distillation of essential oil of rosemary (Rosmarinus officinalis). J. Food Eng. 200, 81–86 (2017)

    Google Scholar 

  13. Crespi, F., Gavagnin, G., Sánchez, D., Martínez, G.S.: Analysis of the thermodynamic potential of supercritical carbon dioxide cycles: a systematic approach. J. Eng. Gas Turbines Power 140, 051701 (2018)

    Google Scholar 

  14. Daly, S.R., Fathi, A., Bahramian, B., Manavitehrani, I., McClure, D.D., Valtchev, P., Schindeler, A., Dehghani, F., Kavanagh, J.M.: A green process for the purification of biodegradable poly(β-hydroxybutyrate). J. Supercrit. Fluids 135, 84–90 (2018)

    Google Scholar 

  15. Embuscado, M.E.: Spices and herbs: natural sources of antioxidants: a mini review. J. Funct. Foods 18, 811–819 (2015).

    Google Scholar 

  16. Esquivel-Hernández, D.A., Rodríguez-Rodríguez, J., Cuéllar-Bermúdez, S.P., García-Pérez, J.S., Mancera-Andrade, E.I., Núñez-Echevarría, J.E., Ontiveros-Valencia, A., Rostro-Alanis, M., García-García, R.M., Torres, J.A., Chen, W.N., Parra-Saldívar, R.: Effect of supercritical carbon dioxide extraction parameters on the biological activities and metabolites present in extracts from Arthrospira platensis. Mar. Drugs 15, 174 (2017)

    Google Scholar 

  17. Fernandes, R.V.B., Guimarães, I.C., Ferreira, C.L.R., Botrel, D.A., Borges, S.V., de Souza, A.U.: Microencapsulated rosemary (Rosmarinus officinalis) essential oil as a biopreservative in Minas Frescal cheese. J. Food Process. Preserv. 41, e12759 (2017)

    Google Scholar 

  18. Genena, A.K., Hense, H., Smânia Junior, A., Souza, S.M.D: Rosemary (Rosmarinus officinalis): a study of the composition, antioxidant and antimicrobial activities of extracts obtained with supercritical carbon dioxide. Food Sci. Technol. 28, 463–469 (2008)

    Google Scholar 

  19. Gouveia, A.R., Alves, M., de Almeida, J.M.M.M., Monteiro-Silva, F., González-Aguilar, G., Silva, J.A., Saraiva, C.: The antimicrobial effect of essential oils against Listeria monocytogenes in sous vide cook-chill beef during storage. J. Food Process. Preserv. 41, e13066 (2017)

    Google Scholar 

  20. Goyeneche, R., Fanovich, A., Rodriguez Rodrigues, C., Nicolao, M.C., Di Scala, K.: Supercritical CO2 extraction of bioactive compounds from radish leaves: yield, antioxidant capacity and cytotoxicity. J. Supercrit. Fluids 135, 78–83 (2018)

    Google Scholar 

  21. Grace, M.H., Qiang, Y., Sang, S., Lila, M.A.: One-step isolation of carnosic acid and carnosol from rosemary by centrifugal partition chromatography. J. Sep. Sci. 40, 1057–1062 (2017)

    Google Scholar 

  22. Güçlü-Üstündağ, Ö, Temelli, F.: Solubility behavior of ternary systems of lipids, cosolvents and supercritical carbon dioxide and processing aspects. J. Supercrit. Fluids 36, 1–15 (2005)

    Google Scholar 

  23. Hammer, K.A., Carson, C.F., Riley, T.V.: Effects of Melaleuca alternifolia (tea tree) essential oil and the major monoterpene component terpinen-4-ol on the development of single- and multistep antibiotic resistance and antimicrobial susceptibility. Antmicrob. Agents Chemother. 56, 909–915 (2012)

    Google Scholar 

  24. Hernandez, D.A., Tenorio, F.J.: Reactivity indexes of antioxidant molecules from Rosmarinus officinalis. Struct. Chem. https://doi.org/10.1007/s11224-017-1066-0. (2017)

    Article  Google Scholar 

  25. Herrero, M., Plaza, M., Cifuentes, A., Ibáñez, E.: Green processes for the extraction of bioactives from rosemary: chemical and functional characterization via ultra-performance liquid chromatography-tandem mass spectrometry and in-vitro assays. J. Chromatogr. 1217, 2512–2520 (2010)

    Google Scholar 

  26. Hosni, K., Hassen, I., Chaâbane, H., Jemli, M., Dallali, S., Sebei, H., Casabianca, H.: Enzyme-assisted extraction of essential oils from thyme (Thymus capitatus L.) and rosemary (Rosmarinus officinalis L.): impact on yield, chemical composition and antimicrobial activity. Ind. Crops Prod. 47, 291–299 (2013)

    Google Scholar 

  27. Ivanova, M., Kareth, S., Petermann, M.: Supercritical carbon dioxide and imidazolium based ionic liquids applied during the sol–gel process as suitable candidates for the replacement of classical organic solvents. J. Supercrit. Fluids 132, 76–82 (2018)

    Google Scholar 

  28. Jiang, Y., Wu, N., Fu, Y.-J., Wang, W., Luo, M., Zhao, C.-J., Zu, Y.-G., Liu, X.-L.: Chemical composition and antimicrobial activity of the essential oil of rosemary. Environ. Toxicol. Pharmacol. 32, 63–68 (2011)

    Google Scholar 

  29. Justo, O.R., Simioni, P.U., Gabriel, D.L., Tamashiro, W.MdS.C., Rosa, PdT.V., Moraes, ÂM.: Evaluation of in vitro anti-inflammatory effects of crude ginger and rosemary extracts obtained through supercritical CO2 extraction on macrophage and tumor cell line: the influence of vehicle type. BMC Complement. Altern. Med. 15, 390 (2015)

    Google Scholar 

  30. Leal, P.F., Braga, M.E., Sato, D.N., Carvalho, J.E., Marques, M.O., Meireles, M.A.A.: Functional properties of spice extracts obtained via supercritical fluid extraction. J. Agric. Food Chem. 51, 2520–2525 (2003)

    Google Scholar 

  31. Mazzutti, S., Rodrigues, L.G.G., Mezzomo, N., Venturi, V., Ferreira, S.R.S.: Integrated green-based processes using supercritical CO2 and pressurized ethanol applied to recover antioxidant compouds from cocoa (Theobroma cacao) bean hulls. J. Supercrit. Fluids 135, 52–59 (2018)

    Google Scholar 

  32. Mezza, G.N., Borgarello, A.V., Grosso, N.R., Fernandez, H., Pramparo, M.C., Gayol, M.F.: Antioxidant activity of rosemary essential oil fractions obtained by molecular distillation and their effect on oxidative stability of sunflower oil. Food Chem. 242, 9–15 (2018)

    Google Scholar 

  33. Moncada, J., Tamayo, J.A., Cardona, C.A.: Techno-economic and environmental assessment of essential oil extraction from oregano (Origanum vulgare) and rosemary (Rosmarinus officinalis) in Colombia. J. Clean. Prod. 112, 172–181 (2016)

    Google Scholar 

  34. Mondello, F., De Bernardis, F., Girolamo, A., Cassone, A., Salvatore, G.: In vivo activity of terpinen-4-ol, the main bioactive component of Melaleuca alternifolia Cheel (tea tree) oil against azole-susceptible and -resistant human pathogenic Candida species. BMC Infect. Dis. 6, 158 (2006)

    Google Scholar 

  35. Ortíz-Ardila, A.E., Correa-Cuadros, J.P., Celis-Zambrano, C.A., Rodríguez-Bocanegra, M.X., Robles-Camargo, J., Sequeda-Castañeda, L.G.: Antioxidant and antimicrobial capacity Cecropia mutisiana Mildbr. (Cecropiaceae) leave extracts. Emirates J. Food Agric. 29, 25–35 (2017)

    Google Scholar 

  36. Pasquel Reátegui, J.L., Machado, A.P.F., Barbero, G.F., Rezende, C.A., Martínez, J.: Extraction of antioxidant compounds from blackberry (Rubus sp.) bagasse using supercritical CO2 assisted by ultrasound. J. Supercrit. Fluids 94, 223–233 (2014)

    Google Scholar 

  37. Paula, J.T., Sousa, I.M.O., Foglio, M.A., Cabral, F.A.: Selective fractionation of extracts of Arrabidaea chica Verlot using supercritical carbon dioxide as antisolvent. J. Supercrit. Fluids 133, 9–16 (2018)

    Google Scholar 

  38. Pintore, G., Usai, M., Bradesi, P., Juliano, C., Boatto, G., Tomi, F., Chessa, M., Cerri, R., Casanova, J.: Chemical composition and antimicrobial activity of Rosmarinus officinalis L. oils from Sardinia and Corsica. Flavour Fragr. J. 17, 15–19 (2002)

    Google Scholar 

  39. Prior, R.L., Wu, X., Schaich, K.: Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem. 53, 4290–4302 (2005)

    Google Scholar 

  40. PubChem Eucalyptol. Available at: https://pubchem.ncbi.nlm.nih.gov/compound/Eucalyptol#section=Top (2018). Accessed 20 July 2018

  41. Roodpeyma, M., Guigard, S.E., Stiver, W.H.: Pressure control of a continuous pilot scale supercritical fluid extraction (SFE) process. J. Supercrit. Fluids 135, 120–129 (2018)

    Google Scholar 

  42. Sahena, F., Zaidul, I., Jinap, S., Karim, A., Abbas, K., Norulaini, N., Omar, A.: Application of supercritical CO2 in lipid extraction–a review. J. Food Eng. 95, 240–253 (2009)

    Google Scholar 

  43. Sánchez-Camargo, A., García-Cañas, V., Herrero, M., Cifuentes, A., Ibáñez, E.: Comparative study of green sub- and supercritical processes to obtain carnosic acid and carnosol-enriched rosemary extracts with in vitro anti-proliferative activity on colon cancer cells. Int. J. Mol. Sci. 17, 2046 (2016)

    Google Scholar 

  44. Sánchez-Camargo, A.D.P., Valdés, A., Sullini, G., García-Cañas, V., Cifuentes, A., Ibáñez, E., Herrero, M.: Two-step sequential supercritical fluid extracts from rosemary with enhanced anti-proliferative activity. J. Funct. Foods 11, 293–303 (2014)

    Google Scholar 

  45. Santoyo, S., Jaime, L., García-Risco, M.R., Ruiz-Rodríguez, A., Reglero, G.: Antiviral properties of supercritical CO2 extracts from oregano and sage. Int. J. Food Prop. 17, 1150–1161 (2014)

    Google Scholar 

  46. Shan, B., Cai, Y.Z., Sun, M., Corke, H.: Antioxidant capacity of 26 spice extracts and characterization of their phenolic constituents. J. Agric. Food Chem. 53, 7749–7759 (2005)

    Google Scholar 

  47. Sharif, K.M., Rahman, M.M., Azmir, J., Mohamed, A., Jahurul, M.H.A., Sahena, F., Zaidul, I.S.M.: Experimental design of supercritical fluid extraction: a review. J. Food Eng. 124, 105–116 (2014)

    Google Scholar 

  48. Sovilj, M.N., Nikolovski, B.G., Spasojević, M.: Critical review of supercritical fluid extraction of selected spice plant materials. Maced. J. Chem. Chem. Eng. 30, 197–220 (2011)

    Google Scholar 

  49. Tena, M., Valcarcel, M., Hidalgo, P., Ubera, J.: Supercritical fluid extraction of natural antioxidants from rosemary: comparison with liquid solvent sonication. Anal. Chem. 69, 521–526 (1997)

    Google Scholar 

  50. Vallverdú-Queralt, A., Regueiro, J., Martínez-Huélamo, M., Alvarenga, J.F.R., Leal, L.N., Lamuela-Raventos, R.M.: A comprehensive study on the phenolic profile of widely used culinary herbs and spices: rosemary, thyme, oregano, cinnamon, cumin and bay. Food Chem. 154, 299–307 (2014)

    Google Scholar 

  51. Vicente, G., Molina, S., González-Vallinas, M., García-Risco, M.R., Fornari, T., Reglero, G., de Molina, A.R.: Supercritical rosemary extracts, their antioxidant activity and effect on hepatic tumor progression. J. Supercrit. Fluids 79, 101–108 (2013)

    Google Scholar 

  52. Vieitez, I., Maceiras, L., Jachmanián, I., Alborés, S.: Antioxidant and antibacterial activity of different extracts from herbs obtained by maceration or supercritical technology. J. Supercrit. Fluids 133, 58–64 (2018)

    Google Scholar 

  53. Viveiros, R., Karim, K., Piletsky, S.A., Heggie, W., Casimiro, T.: Development of a molecularly imprinted polymer for a pharmaceutical impurity in supercritical CO2: rational design using computational approach. J. Clean. Prod. 168, 1025–1031 (2017)

    Google Scholar 

  54. Wenzel, J., Storer Samaniego, C., Wang, L., Burrows, L., Tucker, E., Dwarshuis, N., Ammerman, M., Zand A.: Antioxidant potential of Juglans nigra, black walnut, husks extracted using supercritical carbon dioxide with an ethanol modifier. Food Sci. Nutr. 5, 223–232 (2017)

    Google Scholar 

  55. Xie, J., VanAlstyne, P., Yang, X.: A review on rosemary as a natural antioxidation solution. Eur. J. Lipid Sci. Technol. 119, 1–10 (2017)

    Google Scholar 

  56. Zacconi, F.C., Cabrera, A.L., Ordoñez-Retamales, F., del Valle, J.M., de la Fuente, J.C.: Isothermal solubility in supercritical carbon dioxide of solid derivatives of 2,3-dichloronaphthalene-1,4-dione (dichlone): 2-(Benzylamino)-3-chloronaphthalene-1,4-dione and 2-chloro-3-(phenethylamino)naphthalene-1,4-dione. J. Supercrit. Fluids 129, 75–82 (2017)

    Google Scholar 

  57. Zermane, A., Larkeche, O., Meniai, A.-H., Crampon, C., Badens, E.: Optimization of Algerian rosemary essential oil extraction yield by supercritical CO2 using response surface methodology. C. R. Chim. 19, 538–543 (2016)

    Google Scholar 

  58. Zêzere, B., Magalhães, A.L., Portugal, I., Silva, C.M.: Diffusion coefficients of eucalyptol at infinite dilution in compressed liquid ethanol and in supercritical CO2/ethanol mixtures. J. Supercrit. Fluids 133, 297–308 (2018)

    Google Scholar 

Download references

Acknowledgements

The present work was supported by the project PEI CONACyT (221518, 2015) in collaboration with Tecnologia Ambiental Biomex. We acknowledge the support of the research group of Emerging Technologies and Molecular Nutrition, Food, Pharmaceutical and Bioproducts Development from Tecnologico de Monterrey, Campus Monterrey.

Author information

Authors and Affiliations

  1. Tecnologico de Monterrey, Escuela de Ingenieria y Ciencias, Campus Monterrey, Ave. Eugenio Garza Sada 2501, 64849, Monterrey, NL, Mexico

    J. Saúl García-Pérez, Sara Paulina Cuéllar-Bermúdez, Alejandra Arévalo-Gallegos, Carmen Salinas-Salazar, José Rodríguez-Rodríguez, Reynaldo de la Cruz-Quiroz, Hafiz M. N. Iqbal & Roberto Parra-Saldívar

Authors
  1. J. Saúl García-Pérez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sara Paulina Cuéllar-Bermúdez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alejandra Arévalo-Gallegos
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Carmen Salinas-Salazar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. José Rodríguez-Rodríguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Reynaldo de la Cruz-Quiroz
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hafiz M. N. Iqbal
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Roberto Parra-Saldívar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Hafiz M. N. Iqbal or Roberto Parra-Saldívar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

García-Pérez, J.S., Cuéllar-Bermúdez, S.P., Arévalo-Gallegos, A. et al. Influence of Supercritical CO2 Extraction on Fatty Acids Profile, Volatile Compounds and Bioactivities from Rosmarinus officinalis. Waste Biomass Valor 11, 1527–1537 (2020). https://doi.org/10.1007/s12649-018-0408-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12649-018-0408-5

Keywords

Search

Navigation