Cyclodextrins and food preservatives

Created by: Juan Mejuto

     

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J.C. Mejuto[1], J. Simal-Gándara[2]

Cyclodextrins (CDs) are cyclic α-D-glucopyranose oligomers which are often described as a torus, but in somewhat more realistically pictures as a “shallow truncated cone”.[3] The most important feature of CDs is their cavity due to enable them to form host-guest complex .[4][5][6][7][8]  The formation of these inclusion complexes with small molecular guests of an appropriate size, shape and polarity It is precisely for this reason that they are often drawing up to brush over additives for long-term preservation of food. Typically, microencapsulation focuses on increasing the water solubility of lipophilic substances

Scheme of CDs inclusion complexes formation.

Scheme of CDs inclusion complexes formation. Form Akita et al., 2014[9] 

In the literature there are numerous examples where the use of certain antimicrobial agents can be added to food through microencapsulated with CDs.[10][11][12][13][14][15] In addition, significant increases in its effectiveness have been observed when these are applied in host-guest complexes formed with CDs versus their application as free molecules.

CDs (α-, β- and γ- cyclodextrins). Form Chaplin web page, 2018[16]

In this way, for example, the antimicrobial allyl isothiocyanate is used as food preservative and in the literature has been demonstrated a better performance applied entrapped in β-CD than un-entrapped. In fact, its shelf life of fresh cut onions gets increases in a significant way when it is applied as CD host-guest complexes.[17]

The use of CDs host-guest complexes instead of the free substance offers the benefit of being applied more regularly, maintaining its effect on the food for longer and being used in a more accurate dosage. All this avoids possible toxic effects upon the products and significantly reduces the possible undesirable organoleptic modifications to guarantee food safety and the success of the product in the market.

Additives as hexanal[18], thymol[19], eugenol[20][21] and/or essential oils which contain them, are examples of such additives used as food preservatives and potential hots-guest complex formers with CDs. This way, solubility of these substances is increased so they can easier penetrate the vegetable, but also off-flavours associated to some of them can be reduced maintaining antimicrobial effect.

 

The shelf life of fresh produce is always a problem to be solved by food technologists. Washes with water or treatments with chlorine are an effective tool against the microbiota found on the surface of fruits and vegetables. However, these traditional treatments are not capable of efficiently destroying the internalized microorganisms. For this purpose, it has been demonstrated that ionizing radiation is capable of affecting these pathogens, eliminating them in a satisfactory manner. Unfortunately, these ionizing radiations also damage the product, reducing its quality before the market and causing shrinkage is its organoleptic characteristics or its nutritional properties. However, there is evidence in the literature that this method may be more viable the use of ionizing raditatons, since the addition of β-CD inclusion complexes with different essential oils causes an increase in the radiation sensitivity of microorganisms[22]. It is evident that the possibility of reducing the amount of radiation supplied to the fruit or to the vegetable will also imply a reduction of the losses in the commercial and nutritive value that the ionizing radiation causes on them.

Finally, microencapsulation with CDs, as indicated in the literature, allows the recovery of residual liquids from food processing[23]. Li et al. use the bleaching liquids of two edible fungi to prepare a natural origin antioxidant powder with potentially suitable for food.  

References

  1. Departamento de Química Física, Facultad de Ciencias, Universidad de Vigo, Campus de Ourense, 32004-Ourense, SPAIN
  2. Area de Bromatología, Facultad de Ciencias, Universidad de Vigo, Campus de Ourense, 32004-Ourense, SPAIN
  3. Kenneth A. Connors; The Stability of Cyclodextrin Complexes in Solution. Chemical Reviews 1970, 97, 1325-1358, 10.1021/cr960371r.
  4. Helmut Ritter; Superstructures with cyclodextrins: Chemistry and applications. Beilstein Journal of Organic Chemistry 1970, 8, 1303-1304, 10.3762/bjoc.8.148.
  5. Gerhard Wenz; Superstructures with cyclodextrins: Chemistry and applications II. Beilstein Journal of Organic Chemistry 1970, 11, 271-272, 10.3762/bjoc.11.30.
  6. Gerhard Wenz; Eric Monflier; Superstructures with cyclodextrins: chemistry and applications III. Beilstein Journal of Organic Chemistry 1970, 12, 937-938, 10.3762/bjoc.12.91.
  7. Gerhard Wenz; Superstructures with cyclodextrins: Chemistry and applications IV. Beilstein Journal of Organic Chemistry 1970, 13, 2157-2159, 10.3762/bjoc.13.215.
  8. Gonzalo Astray; Juan C. Mejuto; Jorge Morales; R. Rial-Otero; Jesus Simal-Gandara; Factors controlling flavors binding constants to cyclodextrins and their applications in foods. Food Research International 1970, 43, 1212-1218, 10.1016/j.foodres.2010.02.017.
  9. Tomoki Akita; Keisuke Yoshikiyo; Tatsuyuki Yamamoto; Formation of 1:1 and 2:1 host–guest inclusion complexes of α-cyclodextrin with cycloalkanols: A 1H and 13C NMR spectroscopic study. Journal of Molecular Structure 1970, 1074, 43-50, 10.1016/j.molstruc.2014.05.051.
  10. Laura Higueras; Gracia López-Carballo; Pilar Hernández-Muñoz; Ramón Catalá; Rafael Gavara; Antimicrobial packaging of chicken fillets based on the release of carvacrol from chitosan/cyclodextrin films. International Journal of Food Microbiology 1970, 188, 53-59, 10.1016/j.ijfoodmicro.2014.07.018.
  11. Xi Hai Hao; Ping Jiang; The Application of PVA Antibacterial Film with Clove Oil/β-Cyclodextrin Inclusion Complex in Fruit Packaging. Advanced Materials Research 1970, 655, 1971-1974, 10.4028/www.scientific.net/amr.655-657.1971.
  12. Gonzalo Astray; C. Gonzalez-Barreiro; Juan C. Mejuto; R. Rial-Otero; Jesus Simal-Gandara; A review on the use of cyclodextrins in foods. Food Hydrocolloids 1970, 23, 1631-1640, 10.1016/j.foodhyd.2009.01.001.
  13. Jaruporn Rakmai; Benjamas Cheirsilp; Juan Carlos Mejuto; Ana Torrado-Agrasar; Jesús Simal-Gándara; Physico-chemical characterization and evaluation of bio-efficacies of black pepper essential oil encapsulated in hydroxypropyl-beta-cyclodextrin. Food Hydrocolloids 1970, 65, 157-164, 10.1016/j.foodhyd.2016.11.014.
  14. Jaruporn Rakmai; Benjamas Cheirsilp; Ana Torrado-Agrasar; Jesús Simal-Gándara; Juan Carlos Mejuto; Encapsulation of yarrow essential oil in hydroxypropyl-beta-cyclodextrin: physiochemical characterization and evaluation of bio-efficacies. CyTA - Journal of Food 1970, 15, 1-9, 10.1080/19476337.2017.1286523.
  15. Jaruporn Rakmai; Benjamas Cheirsilp; Juan Carlos Mejuto; Jesús Simal-Gándara; Ana Torrado-Agrasar; Antioxidant and antimicrobial properties of encapsulated guava leaf oil in hydroxypropyl-beta-cyclodextrin. Industrial Crops and Products 1970, 111, 219-225, 10.1016/j.indcrop.2017.10.027.
  16. Water structure and science: Cyclodextrins . Water structure and science. Retrieved 2018-9-26
  17. M.J. Piercey; G. Mazzanti; S.M. Budge; P.J. Delaquis; A.T. Paulson; Lisbeth Truelstrup Hansen; Antimicrobial activity of cyclodextrin entrapped allyl isothiocyanate in a model system and packaged fresh-cut onions. Food Microbiology 1970, 30, 213-218, 10.1016/j.fm.2011.10.015.
  18. Natalia E. Sáenz-Garza; Timothy Durance; Pascal Delaquis; Microencapsulation of hexanal by radiant energy vacuum microwave-molecular inclusion for controlled release and inhibition of Penicillium expansum in a model system and on apple tissue. Food Research International 1970, 52, 496-502, 10.1016/j.foodres.2013.01.040.
  19. Feifei Tao; Laura E. Hill; Yankun Peng; Carmen L. Gomes; Synthesis and characterization of β-cyclodextrin inclusion complexes of thymol and thyme oil for antimicrobial delivery applications. LWT 1970, 59, 247-255, 10.1016/j.lwt.2014.05.037.
  20. Liang Gong; Taotao Li; Feng Chen; Xuewu Duan; Yunfei Yuan; Dandan Zhang; Yueming Jiang; An inclusion complex of eugenol into β-cyclodextrin: Preparation, and physicochemical and antifungal characterization. Food Chemistry 1970, 196, 324-330, 10.1016/j.foodchem.2015.09.052.
  21. Liang Gong; Taotao Li; Feng Chen; Xuewu Duan; Yunfei Yuan; Dandan Zhang; Yueming Jiang; Corrigendum to “An inclusion complex of eugenol into β-cyclodextrin: Preparation, and physicochemical and antifungal characterization” [Food Chem. 196 (2016) 324–330]. Food Chemistry 1970, 206, 292, 10.1016/j.foodchem.2016.03.091.
  22. Carmen Gomes; Rosana G. Moreira; Elena Castell-Perez; Elena Castell‐Perez; Microencapsulated Antimicrobial Compounds as a Means to Enhance Electron Beam Irradiation Treatment for Inactivation of Pathogens on Fresh Spinach Leaves. Journal of Food Science 1970, 76, E479-E488, 10.1111/j.1750-3841.2011.02264.x.
  23. Li Y.; Lai, P.; Chen, J.; Shen, H.; Wu, L.; Tang, B.; Physicochemical and Antioxidant Properties of Spray Drying Powders from Stropharia rugoso-annulata and Agaricus brunnescens Blanching Liquid. Advanced Journal of Food Science and Technology 2015, 9, 372-378, 10.19026/ajfst.9.1918.
  24. Kenneth A. Connors; The Stability of Cyclodextrin Complexes in Solution. Chemical Reviews 1970, 97, 1325-1358, 10.1021/cr960371r.