Advertisement

Crystallisation properties of amorphous cyclodextrin powders and their complexation with fish oil

  • Lukas Frieler
  • Thao M. Ho
  • Anita Anthony
  • Yoshii Hidefumi
  • Anya J. E. Yago
  • Bhesh R. BhandariEmail author
Original Article

Abstract

Water-induced crystallisation of amorphous core-cyclodextrin (CD) complex is an essential step in a solid encapsulation process and removal of added water is a challenging. Ethanol addition is expected to shorten the complex dehydration time. This study investigated crystallisation of amorphous spray-dried α-, β- and γ-CD powders by direct mixing 15% (w/w) of ethanol:water mixture (0:100, 20:80, 40:60, 60:40, 80:20 and 100:0) over 72 h period. The results showed α- and β-CD powders crystallised at all concentrations of ethanol solutions. Especially mixed with 0:100 and 20:80 ethanol:water solutions, the crystallisation behaviour of α- and β-CD powders was similar to that of commercial crystalline counterparts. γ-CD powders exhibited a crystallisation sign as mixed with 0:100 and 20:80 ethanol:water solutions only. In the study of fish oil encapsulation using the mixture of water and ethanol to induce the complex crystallisation, only γ-CD powder was able to form complex with fish oil.

Keywords

Cyclodextrin powder Fish oil Amorphous powder Ethanol-induced crystallisation Solid encapsulation 

Notes

Acknowledgements

The authors acknowledge the facilities, and the scientific and technical assistance, of School of Agriculture and Food Sciences and the Australian Microscopy and Microanalysis Research Facility at the Centre for Microscopy and Microanalysis, The University of Queensland.

References

  1. Aree T, Chaichit N (2008) Crystal form III of beta-cyclodextrin-ethanol inclusion complex: layer-type structure with dimeric motif. Carbohydr Res 34:2285–2291.  https://doi.org/10.1016/j.carres.2008.04.028 CrossRefGoogle Scholar
  2. Astray G, Gonzalez-Barreiro C, Mejut JC, Rial-Otero R, Simal-Gandar J (2009) A review on the use of cyclodextins in foods. Food Hydrocoll 23:1631–1640.  https://doi.org/10.1016/j.foodhyd.2009.01.001 CrossRefGoogle Scholar
  3. Bellitz H, Grosch W, Schieberle P (2009) Food chemistry. Springer, BerlinGoogle Scholar
  4. Bhandari BR, D’Arcy BR, Padukka I (1999) Encapsulation of lemon oil by paste method using beta-cyclodextrin: encapsulation efficiency and profile of oil volatiles. J Agric Food Chem 47(12):5194–5197.  https://doi.org/10.1021/jf9902503 CrossRefGoogle Scholar
  5. Cameron-Smith D, Albert B, Cutfield W (2015) Fishing for answers: is oxidation of fish oil supplements a problem? J Nutr Sci 4:1–2.  https://doi.org/10.1017/jns.2015.26 CrossRefGoogle Scholar
  6. Chan E (2011) Preparation of Ca-alginate beads containing high oil content: influence of process variables on encapsulation efficiency and bead properties. Carbohydr Polym 84:1267–1275.  https://doi.org/10.1016/j.carbpol.2011.01.015 CrossRefGoogle Scholar
  7. Choi MJ, Ruktanonchai U, Min SG, Chun JY, Soottitantawat A (2010) Physical characteristics of fish oil encapsulated by beta-cyclodextrin using an aggregation method or polycaprolactone using an emulsion-diffusion method. Food Chem 119(4):1694–1703.  https://doi.org/10.1016/j.foodchem.2009.09.052 CrossRefGoogle Scholar
  8. Chung C, Sanguansri L, Augustin M (2010) Resistant starch modification: effects on starch properties and functionality as co-encapsulant in sodium caseinate-based fish oil microcapsules. J Food Sci 75(9):636–642.  https://doi.org/10.1111/j.1750-3841.2010.01857.x CrossRefGoogle Scholar
  9. Coey JMD (1974) Amorphous solids: a review of the applications of the Mössbauer effect. J Phys Colloq 35:C6-89–C6-105.  https://doi.org/10.1051/jphyscol:1974608 Google Scholar
  10. Franco M, Araújo D, de Paula E. Cavalcanti L, Yokaichiya F (2017) X-ray scattering techniques applied in the development of drug delivery systems. X-ray Scattering, Alicia Esther Ares, IntechOpen,  https://doi.org/10.5772/65326. https://www.intechopen.com/books/x-ray-scattering/x-ray-scattering-techniques-applied-in-the-development-of-drug-delivery-systems. Accessed 26 June 2015
  11. FSANZ (2004) Final assessment report: Alpha-cyclodextrin as a novel food. http://www.foodstandards.gov.au/code/applications/Documents/A494_Alpha-Cyclodextrin_as_a_novel_food_IAR.pdf. Accessed 25 Aug 2014
  12. Gharsallaoui A, Roudaut G, Chambi O, Voilley A, Saurel R (2007) Applications of spray-drying in microencapsulation of food ingredients: an overview. Food Res Int 40:1107–1121.  https://doi.org/10.1016/j.foodres.2007.07.004 CrossRefGoogle Scholar
  13. Hădărugă D, Ünlüsayin M, Gruia A, Birău C, Rusu G, Hădărugă N (2016) Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with beta-cyclodextrin. Beilstein J Org Chem 12:179–191.  https://doi.org/10.3762/bjoc.12.20 CrossRefGoogle Scholar
  14. Hedges AR (1998) Industrial applications of cyclodextrins. Chem Rev 98:2035–2044.  https://doi.org/10.1021/cr970014w CrossRefGoogle Scholar
  15. Ho, TM (2017) Studies of the encapsulation and release of carbon dioxide from amorphous and crystalline alpha-cyclodextrin powders and its application in food systems, Ph.D. Thesis, School of Agriculture and Food Sciences, The University of Queensland.  https://doi.org/10.14264/uql.2018.85
  16. Ho TM, Howes T, Bhandari BR (2014) Encapsulation of gases in powder solid matrices and their applications: a review. Powder Technol 259:87–108.  https://doi.org/10.1016/j.powtec.2014.03.054 CrossRefGoogle Scholar
  17. Ho TM, Howes T, Bhandari BR (2015) Characterization of crystalline and spray dried amorphous alpha-cyclodextrin powders. Powder Technol 17(06):585–594.  https://doi.org/10.1016/j.powtec.2015.06.027 CrossRefGoogle Scholar
  18. Ho TM, Truong T, Bhandari BR (2017a) Spray-drying and non-equilibrium states/glass transition. In: Bhandari BR, Roos YH (eds) Non-equilibrium states and glass transitions in foods—processing effects and product-specific implications, Chapter 5. Woodhead Publishing, New York, pp 111–136CrossRefGoogle Scholar
  19. Ho TM, Truong T, Bhandari BR (2017b) Methods to characterize the structure of food powders—a review. Biosci Biotechnol Biochem 12(1):1–21.  https://doi.org/10.1080/09168451.2016.1274643 Google Scholar
  20. Hong J, Shah J, McGonagle M (2011) Effect of cyclodextrin derivation and amorphous state of complex on accelerated degradation of ziprasidone. J Pharm Sci 100(7):2703–2716.  https://doi.org/10.1002/jps.22498 CrossRefGoogle Scholar
  21. Irie T, Uekama K (1997) Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci 86:147–162.  https://doi.org/10.1021/js960213f CrossRefGoogle Scholar
  22. Karathanos V, Mourtzinos I, Yannakopoulou K, Andikopoulos N (2007) Study of the solubility, antioxidant activity and structure of inclusion complex of vanillin with beta-cyclodextrin. Food Chem 101:652–658.  https://doi.org/10.1016/j.foodchem.2006.01.053 CrossRefGoogle Scholar
  23. Klinkesorn U, Sophanodora P, Chinachoti P, Decker E, McClements J (2006) Characterization of spray-dried tuna oil emulsified in two-layered interfacial membranes prepared using electrostatic layer-by-layer deposition. Food Res Int 39(4):449–457.  https://doi.org/10.1016/j.foodres.2005.09.008 CrossRefGoogle Scholar
  24. Marques HMC (2010) A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour Fragr J 25(5):313–326.  https://doi.org/10.1002/ffj.2019 CrossRefGoogle Scholar
  25. Na H, Kim J, Kim J, Lee K (2011) Encapsulation of fish oil using cyclodextrin and whey proteine concentrate. Biotechnol Bioprocess Eng 16(6):1077–1082.  https://doi.org/10.1007/s12257-011-0099-2 CrossRefGoogle Scholar
  26. Patonay G, Fowler K, Shapira A, Nelson G, Warner IM (1987) Cyclodextrin complexes of polyaromatic hydrocarbons in the presence of aliphatic alcohols. J Incl Phenom 5(6):717–723.  https://doi.org/10.1007/BF00656591 CrossRefGoogle Scholar
  27. Reineccius T, Reineccius G, Peppard T (2002) Encapsulation of flavours using cylcodextrins: comparison of flavor retention in alpha, beta and gamma types. Food Chem Toxicol 67:3271–3279.  https://doi.org/10.1111/j.1365-2621.2002.tb09577.x Google Scholar
  28. Shrestha M, Ho TM, Bhandari BR (2017) Encapsulation of tea tree oil by amorphous beta-cyclodextrin powder. Food Chem 221:1474–1483.  https://doi.org/10.1016/j.foodchem.2016.11.003 CrossRefGoogle Scholar
  29. Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1753.  https://doi.org/10.1021/cr970022c CrossRefGoogle Scholar
  30. Szente L, Szejtli J (2004) Cyclodextrins as food ingredients. Trends Food Sci Technol 15(3):137–142.  https://doi.org/10.1016/j.tifs.2003.09.019 CrossRefGoogle Scholar
  31. Taylor LS (2015) Physical stability and crystallization inhibition. In: Newman A (ed) Pharmaceutical amorphous solid dispersions. Wiley, Hoboken, pp 179–217Google Scholar
  32. USDA (2016) National nutrient database for standard reference – fish oil. United States Department of Agriculture. https://ndb.nal.usda.gov/ndb/foods/show/726?n1=%7BQv%3D1%7D&fgcd=&man=&lfacet=&count=&max=50&sort=default&qlookup=04590&offset=&format=Full&new=&measureby=&Qv=1&ds=&qt=&qp=&qa=&qn=&q=&ing =. Accessed 01 Aug 2017

Copyright information

© Association of Food Scientists & Technologists (India) 2019

Authors and Affiliations

  • Lukas Frieler
    • 1
  • Thao M. Ho
    • 2
    • 5
  • Anita Anthony
    • 3
  • Yoshii Hidefumi
    • 4
  • Anya J. E. Yago
    • 6
  • Bhesh R. Bhandari
    • 2
    Email author
  1. 1.Faculty of Process Engineering, Energy and Mechanical SystemsTH KölnCologneGermany
  2. 2.School of Agriculture and Food SciencesThe University of QueenslandBrisbaneAustralia
  3. 3.Nanyang PolytechnicAng Mo KioSingapore
  4. 4.Department of Applied Biological Science, Faculty of AgricultureKagawa UniversityTakamatsuJapan
  5. 5.Food Technology DepartmentAn Giang UniversityLong XuyênVietnam
  6. 6.Centre for Microscopy and MicroanalysisThe University of QueenslandBrisbaneAustralia

Personalised recommendations