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Supercritical Extraction of Carotenoids from Rosa canina L. Hips and their Formulation with β-Cyclodextrin

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Abstract

The purpose of this research was to preliminary assess the suitability of a new method for the preparation of a solid formulation in form of powder composed by β-cyclodextrin and the supercritical extract of Rosa canina hips. The method implies the extraction of carotenoids, in particular β-carotene, from freeze dried fruits of R. canina with supercritical CO2 at 70 °C and 300 bar, in the presence of varying quantity of ethanol as entrainer. The obtained supercritical solution is then expanded at ambient conditions into an aqueous solution of β-cyclodextrin to favour the interaction between β-cyclodextrin and the lipophilic components of the extract. β-carotene solubility (mole fraction) in supercritical CO2 or in supercritical CO2/ethanol mixtures were in the order of 1 10−7. The β-carotene extracted from R. canina fruits (nearly 10 μg/g of dry matrix), interacts almost quantitatively with β-cyclodextrin affording a solid phase, which presents a low apparent solubility in water. Finally the interaction with β-cyclodextrin results in a higher concentration of the β-carotene trans- form relative to the cis- form in the extracted product when collected in an aqueous solution of β-cyclodextrin with respect to the extract in n-hexane.

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References

  1. F. Favati, J. W. King, J. P. Friederich, and K. Eskins. Supercritical CO2 extraction of carotene and lutein from leaf protein concentrates. J. Food Sci. 53:1532–1536 (1988).

    Article  CAS  Google Scholar 

  2. A. V. Rao, and F. G. Rao. Carotenoids and human health. Pharmacol. Res. 55:207–2016 (2007).

    Article  PubMed  CAS  Google Scholar 

  3. M. D. A. Saldaña, L. Sun, S. E. Guigard, and F. Temelli. Comparison of the solubility of β-carotene in supercritical CO2 based on a binary and a multicomponent complex system. J. Supercrit. Fluids. 37:342–349 (2006).

    Article  CAS  Google Scholar 

  4. M. J. O’Neil. The Merck Index, Merck Research Laboratories, Whitehouse, NJ, USA, 2006.

    Google Scholar 

  5. J. Ganguly, M. R. Rao, S. K. Murthy, and K. Sarada. Systemic mode of action of vitamin A. Vitamins and Hormones. 38:1–54 (1980).

    Article  PubMed  CAS  Google Scholar 

  6. G. G. Liand, and A. J. Tan. A case-control study of serum beta-carotene and lung cancer. Zhonghua Yu Fang Yi Xue Za Zhi. 28:81–83 (1994).

    Google Scholar 

  7. T. Hodisan, C. Socaciu, I. Ropan, and G. Neamtu. Carotenoid composition of Rosa canina fruits determined by thin-layer chromatography and high-performance liquid chromatography. J. Pharm. Biomed. Anal. 16:521–528 (1997).

    Article  PubMed  CAS  Google Scholar 

  8. A. Razungles, J. Oszmianski, and J. C. Sapis. Determination of carotenoids in fruits of Rosa sp. (Rosa canina and Rosa rugosa) and of chokeberry (Aronia melanocarpa). J. Food Sci. 54:774–777 (1989).

    Article  CAS  Google Scholar 

  9. V. Böhm, K. Fröhlich, and R. Bitsch. Rosehip a “new” source of lycopene? Molecular Aspects of Medicine. 24:385–389 (2003).

    Article  PubMed  CAS  Google Scholar 

  10. M. Innocenti, L. Niccoli, L. Vasacci, F. F. Vincieri, and N. Mulinacci. Componenti bioattivi nei falsi frutti di cultivars selezionate di Rosa canina, V Congresso Nazionale di Chimica degli Alimenti, Morgan, Milan, 2004, pp. 20–25.

    Google Scholar 

  11. M. D. Macías-Sánchez, C. Mantell, M. Rodríguez, E. Martínez de la Ossa, L. M. Lubián, and O. Montero. Supercritical fluid extraction of carotenoids and chlorophyll a from Synechococcus sp.. J. Supercrit. Fluids. 39:323–329 (2007).

    Article  CAS  Google Scholar 

  12. E. Reverchon, and I. De Marco. Review: supercritical fluid extraction and fractionation of natural matter. J. Supercrit. Fluids. 38:146–166 (2006).

    Article  CAS  Google Scholar 

  13. S. M. Pourmortazavi, and S. S. Hajimirsadeghi. Supercritical fluid extraction in plant essential and volatile oil analysis. J. Chromatogr. A. 1163:2–24 (2007).

    Article  PubMed  CAS  Google Scholar 

  14. P. Subra, S. Castellani, P. Jestin, and A. Aoufi. Extraction of β-carotene with supercritical fluids: Experiments and modelling. J. Supercrit. Fluids. 12:261–269 (1998).

    Article  CAS  Google Scholar 

  15. K. Kalampoukas, and G. A. Dervakos. Process optimization for clean manufacturing: Supercritical fluid extraction for β-carotene production. Computers & Chemical Engineering. 202:S1383–S1388 (2003).

    Google Scholar 

  16. M. L. Cygnarowicz, R. J. Maxwell, and W. D. Seider. Equilibrium solubilities of β-carotene in supercritical CO2. Fluid Phase Equilibria. 59:57.

    Article  CAS  Google Scholar 

  17. K. Sakaki. Solubility of β-carotene in dense CO2 and nitrous oxide from 308–323 K and from 9.6–30 MPa. J. Chem. Eng. Data. 37:249 (1992).

    Article  CAS  Google Scholar 

  18. R. L. Mendes, B. P. Nobre, J. P. Coelho, and A. F. Palavra. Solubility of β-carotene in supercritical carbon dioxide and ethane. J. Supercrit. Fluids. 16:99–106 (1999).

    Article  CAS  Google Scholar 

  19. O. S. V. Illés, M. Then, H. Daood, and S. Perneczki. Extraction of hiprose fruit by supercritical CO2 and propane. The Journal of Supercritical Fluids. 10:209–218 (1997).

    Article  Google Scholar 

  20. E. Reverchon, A. Kaziunas, and C. Marrone. Supercritical CO2 extraction of hiprose seed oil: experiments and mathematical modelling. Chem. Eng. Sci. 55:2195–2201 (2000).

    Article  CAS  Google Scholar 

  21. J. M. del Valle, O. Rivera, M. Mattea, L. Ruetsch, J. Daghero, and A. Flores. Supercritical CO2 processing of pretreated rosehip seeds: effect of process scale on oil extraction kinetics. J. Supercrit. Fluids. 31:159–174 (2004).

    Article  CAS  Google Scholar 

  22. K. Szentmihályi, P. Vinkler, B. Lakatos, V. Illés, and M. Then. Rose hip (Rosa canina L.) oil obtained from waste hip seeds by different extraction methods. Bioresource Technology. 82:195–201 (2002).

    Article  PubMed  Google Scholar 

  23. S. Machmudah, Y. Kawahito, M. Sasaki, and M. Goto. Process optimisation and extraction rate analysis of carotenoids extraction from rosehip fruit using supercritical CO2. J. Supercrit. Fluids. 44:308–314 (2008)doi:doi:10.1016/j.superflu.2007.09.032.

    Article  CAS  Google Scholar 

  24. C. J. Chang, and A. D. Randolph. Precipitation of β-carotene in supercritical fluids. AIChE. 35:1876 (1989).

    Article  CAS  Google Scholar 

  25. A. J. Jay, and D. C. Steytler. Nearcritical fluids as solvents for β-carotene. The Journal of Supercritical Fluids. 5:274 (1992).

    Article  CAS  Google Scholar 

  26. A. J. Jay, D. C. Steytler, and M. Knights. Spectrometric studies of food colours in near-critical CO2. J. Supercrit. Fluids. 4:131 (1991).

    Article  CAS  Google Scholar 

  27. M. J. Cocero, S. González, S. Pérez, and E. Alonso. Supercritical extraction of unsaturated products. Degradation of β-carotene in supercritical extraction processes. J. Supercrit. Fluids. 19:39–44 (2000).

    Article  CAS  Google Scholar 

  28. H. G. Choi, and D. D. Kim. Improvement of dissolution and bioavailability of nifendipine by inclusion in hydroxypropyl-β-cyclodextrin. Drug Dev Ind Pharm. 29:1085–1094 (2003).

    Article  PubMed  CAS  Google Scholar 

  29. G. Z. Feng, and K. Lu. Study on the inclusion complexation interaction of beta-cyclodextrin and beta-carotene by UV–Vis spectra. Guang Pu Xue Yu Guang Pu Fen Xi. 24:1099–1102 (2004).

    PubMed  CAS  Google Scholar 

  30. S. Rawat, and S. K. Jain. Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes. Eur J Pharm Biopharm. 57:263–267 (2004).

    Article  PubMed  CAS  Google Scholar 

  31. R. Bettini, C. D'Andria, P. L. Catellani, P. Santi, G. Massimo, D. Cocconi, and P. Colombo. Nicotine nasal powder: design and characterisation. S.T.P. Pharma Sciences. 9:457–462 (1999).

    CAS  Google Scholar 

  32. I. Lancrajan, H. A. Diehl, C. Socaciu, M. Engelke, and M. Zorn-Kruppa. Carotenoid incorporation into natural membranes from artificial carriers: liposomes and β-cyclodextrins. Chemistry and Physics of Lipids. 112:1–10 (2001).

    Article  PubMed  CAS  Google Scholar 

  33. C. S. Kaiser, H. Rompp, and P. C. Schmidt. Supercritical carbon dioxide extraction of chamomile flowers: extraction efficiency, stability, and in-line inclusion of chamomile–carbon dioxide extract in β-cyclodextrin. Phytochem. Anal. 15:249–256 (2004).

    Article  PubMed  CAS  Google Scholar 

  34. D. Y. Peng, and D. B. Robinson. A new two-constant equation of state. Ind. Eng. Chem. Fundam. 15:59–64 (1976).

    Article  CAS  Google Scholar 

  35. C. J. Chang, C.-Y. Day, C.-M. Ko, and K.-L. Chiu. Densities and P–x–y diagrams for carbon dioxide dissolution in methanol, ethanol and acetone mixtures. Fluid Phase Equilibria. 131:243–258 (1997).

    Article  CAS  Google Scholar 

  36. A. Stassi, R. Bettini, A. Gazzaniga, F. Giordano, and A. Schiraldi. Assessment of solubility of ketoprofen and vanillic acid in supercritical CO2 under dynamic conditions. J. Chem. Eng. Data. 45:161–165 (2000).

    Article  CAS  Google Scholar 

  37. R. Bettini, L. Bonassi, V. Castoro, A. Rossi, L. Zema, A. Gazzaniga, and F. Giordano. Solubility and conversion of carbamazepine polymorphs in supercritical carbon dioxide. Eur. J. Pharm. Sci. 13:281–286 (2001).

    Article  PubMed  CAS  Google Scholar 

  38. M. Johannsen, and G. Brunner. Solubilities of the fat-soluble vitamins A, D, E, and K in supercritical carbon dioxide. J. Chem. Eng. Data. 42:106–11 (1997).

    Article  CAS  Google Scholar 

  39. T. Higuchi, and K. Connors. Phase-solubility techniques. Adv. Anal. Chem. Instr. 5:117–212 (1965).

    Google Scholar 

  40. L. Szente, K. Mikuni, H. Hashimoto, and J. Szejtli. Stabilization and solubilization of lipophilic natural colorants with cyclodextrins. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry. 32:81–89 (1998).

    Article  CAS  Google Scholar 

  41. N. E. Polyakov, T. V. Leshina, T. A. Konovalova, E. O. Hand, and L. D. Kispert. Inclusion complexes of carotenoids with cyclodextrins: HNMR, EPR, and optical studies. Free Radical Biology and Medicine. 36:872–880 (2004).

    Article  PubMed  CAS  Google Scholar 

  42. E. Vági, B. Simándi, K. P. Vásárhelyiné, H. Daood, Á. Kéry, F. Doleschall, and B. Nagy. Supercritical carbon dioxide extraction of carotenoids, tocopherols and sitosterols from industrial tomato by-products. J. Supercrit. Fluids. 40:218–226 (2007).

    Article  CAS  Google Scholar 

  43. İ. S. Şanal, E. E. Bayraktar, Ü. Mehmetoğlu, and A. Çalımlı. Determination of optimum conditions for SC-(CO2 + ethanol) extraction of β-carotene from apricot pomace using response surface methodology. J. Supercrit. Fluids. 34:331–338 (2005).

    Article  CAS  Google Scholar 

  44. H. Sovová, P. Roumiana, and A. Anatolii. Solubility of β-carotene in supercritical CO2 and the effect of entrainers. J. Supercrit. Fluids. 21:195–203 (2001).

    Article  Google Scholar 

  45. P. H. van Konynenburg, and R. L. Scott. Critical lines and phase equilibria in binary van der Waals mixtures. Phil. Trans. of the Royal Society (London). 298:495–540 (1980).

    Article  Google Scholar 

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Acknowledgement

This work was partially supported by Italian Ministry of University and Research through its PRIN programme.

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Authors and Affiliations

  1. Department of Pharmacy, University of Parma, Viale G.P. Usberti 27/A, 43100, Parma, Italy

    R. Tozzi, K. Storlikken, I. Pasquali & R. Bettini

  2. Department of Pharmaceutical Sciences, University of Florence, Florence, Italy

    N. Mulinacci & F. F. Vincieri

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  1. R. Tozzi
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Correspondence to R. Bettini.

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Tozzi, R., Mulinacci, N., Storlikken, K. et al. Supercritical Extraction of Carotenoids from Rosa canina L. Hips and their Formulation with β-Cyclodextrin. AAPS PharmSciTech 9, 693–700 (2008). https://doi.org/10.1208/s12249-008-9100-6

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