Structural characterization and bioavailability of ternary nanoparticles consisting of amylose, α-linoleic acid and β-lactoglobulin complexed with naringin

International Journal of Biological Macromolecules

Volumn 99, Issue , 2017, Pages 365-374

  Feng, Tao ^a   Wang, Ke ^a   Liu, Fangfang ^a   Ye, Ran ^b   Zhu, Xiao ^c   Zhuang, Haining ^d   Xu, Zhimin ^e  

^a SHANGHAI INSTITUTE OF TECHNOLOGY   (China)

^b Roha USA LLC   (United States)

^c PURDUE UNIVERSITY   (United States)

^d INSTITUTE OF EDIBLE FUNGI   (China)

^e LOUISIANA STATE UNIVERSITY AGRICULTURAL CENTER   (United States)

Author keywords

Bioavailability; Inclusion complex; Naringin; Structural characterization; Ternary nanoparticles

Indexed keywords

AMYLOSE; AURANTIIN; BETA LACTOGLOBULIN; LINOLEIC ACID; NANOPARTICLE; BIOMIMETIC MATERIAL; DRUG CARRIER; FLAVANONE DERIVATIVE; LACTOGLOBULIN; LINOLENIC ACID; WATER;

ARTICLE; BIOAVAILABILITY; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROSCOPY; NANOENCAPSULATION; PARTICLE SIZE; PHYSICAL CHEMISTRY; STRUCTURE ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION; ANIMAL; CHEMISTRY; DRUG RELEASE; GASTROINTESTINAL TRACT; HUMAN; METABOLISM; SOLUBILITY;

ALPHA-LINOLENIC ACID; AMYLOSE; ANIMALS; BIOLOGICAL AVAILABILITY; BIOMIMETIC MATERIALS; DRUG CARRIERS; DRUG LIBERATION; FLAVANONES; GASTROINTESTINAL TRACT; HUMANS; LACTOGLOBULINS; NANOPARTICLES; PARTICLE SIZE; SOLUBILITY; WATER;

EID: 85014454690     PISSN: 01418130     EISSN: 18790003     Source Type: Journal    
DOI: 10.1016/j.ijbiomac.2017.03.005     Document Type: Article

References (59)

1. [1] Erlund, I., Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology. Nutr. Res. 24 (2004), 851–874.
2. [2] Rouseff, R.L., Martin, S.F., Youtsey, C.O., Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus. J. Agric. Food Chem. 35 (1987), 1027–1030.
3. [3] Zou, Z., Xi, W., Hu, Y., Nie, C., Zhou, Z., Antioxidant activity of Citrus fruits. Food Chem. 196 (2016), 885–896.
4. [4] Scalbert, A., Williamson, G., Dietary intake and bioavailability of polyphenols. J. Nutr. 130 (2000), 2073S–2085S.
5. [5] Mamdouh, M.A., Monira, A., The influence of naringin on the oxidative state of rats with streptozotocin-induced acute hyperglycaemia. Zeitschrift für Naturforschung C 59 (2004), 726–733.
6. [6] Jung, U., Kim, H., Lee, J., Lee, M., Kim, H., Park, E., et al. Naringin supplementation lowers plasma lipids and enhances erythrocyte antioxidant enzyme activities in hypercholesterolemic subjects. Clin. Nutr. 22 (2003), 561–568.
7. [7] Kurowska, E., Borradaile, N., Spence, J., Carroll, K., Hypocholesterolemic effects of dietary citrus juices in rabbits. Nutr. Res. 20 (2000), 121–129.
8. [8] So, F.V., Guthrie, N., Chambers, A.F., Moussa, M., Carroll, K.K., Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutr. Cancer, 1996, 167–181.
9. [9] Jeong, K.-W., Lee, J.-Y., Kang, D.-I., Lee, J.-U., Shin, S.Y., Kim, Y., Screening of flavonoids as candidate antibiotics against Enterococcus faecalis. J. Nat. Prod. 72 (2009), 719–724.
10. [10] Lee, K.-A., Moon, S.H., Kim, K.-T., Mendonca, A.F., Paik, H.-D., Antimicrobial effects of various flavonoids on Escherichia coli O157: H7 cell growth and lipopolysaccharide production. Food Sci. Biotechnol. 19 (2010), 257–261.
11. [11] Rice-Evans, C.A., Miller, N.J., Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20 (1996), 933–956.
12. [12] Mielczarek, C., Acid–base properties of selected flavonoid glycosides. Eur. J. Pharm. Sci. 25 (2005), 273–279.
13. [13] Hörter, D., Dressman, J., Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv. Drug Deliv. Rev. 25 (1997), 3–14.
14. [14] Huang, L.-F., Tong, W.-Q.T., Impact of solid state properties on developability assessment of drug candidates. Adv. Drug Deliv. Rev. 56 (2004), 321–334.
15. [15] Gharsallaoui, A., Roudaut, G., Chambin, O., Voilley, A., Saurel, R., Applications of spray-drying in microencapsulation of food ingredients: an overview. Food Res. Int. 40 (2007), 1107–1121.
16. [16] Kanaze, F., Kokkalou, E., Niopas, I., Georgarakis, M., Stergiou, A., Bikiaris, D., Dissolution enhancement of flavonoids by solid dispersion in PVP and PEG matrixes: a comparative study. J. Appl. Polym. Sci. 102 (2006), 460–471.
17. [17] Kanaze, F., Kokkalou, E., Niopas, I., Georgarakis, M., Stergiou, A., Bikiaris, D., Thermal analysis study of flavonoid solid dispersions having enhanced solubility. J. Therm. Anal. Calorim. 83 (2006), 283–290.
18. [18] Ficarra, R., Tommasini, S., Raneri, D., Calabro, M., Di Bella, M., Rustichelli, C., et al. Study of flavonoids/β-cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation. J. Pharm. Biomed. Anal. 29 (2002), 1005–1014.
19. [19] Cui, L., Zhang, Z.-H., Sun, E., Jia, X.-B., Effect of β-cyclodextrin complexation on solubility and enzymatic conversion of naringin. Int. J. Mol. Sci. 13 (2012), 14251–14261.
20. [20] Tolstoguzov, V., Some thermodynamic considerations in food formulation. Food Hydrocoll. 17 (2003), 1–23.
21. [21] Assadpour, E., Jafari, S.M., Maghsoudlou, Y., Evaluation of folic acid release from spray dried powder particles of pectin-whey protein nano-capsules. Int. J. Biol. Macromol. 95 (2017), 238–247.
22. [22] Taha, F., Mohamed, S., Effect of different denaturating methods on lipid–protein complex formation. LWT–Food Sci. Technol. 37 (2004), 99–104.
23. [23] Eliasson, A.-C., Carbohydrates in Food. 2006, CRC press.
24. [24] Faridi, E.A., Jafari, S.M., Biopolymer nano-particles and natural nano-carriers for nano-encapsulation of phenolic compounds. Colloids Surf. B Biointerfaces, 146, 2016, 532.
25. [25] Zhang, G., A Novel Three-way Interaction Among Starch, Protein, and Free-fatty Acid: Functionality and Mechanism Elucidation. 1999.
26. [26] Zhang, G., Hamaker, B.R., A three component interaction among starch, protein, and free fatty acids revealed by pasting profiles. J. Agric. Food Chem. 51 (2003), 2797–2800.
27. [27] Zhang, G., Maladen, M.D., Hamaker, B.R., Detection of a novel three component complex consisting of starch, protein, and free fatty acids. J. Agric. Food Chem. 51 (2003), 2801–2805.
28. [28] Zhang, G., Hamaker, B.R., Sorghum (Sorghum bicolor L. Moench) flour pasting properties influenced by free fatty acids and protein 1. Cereal Chem. 82 (2005), 534–540.
29. [29] Liu, J., Fei, L., Maladen, M., Hamaker, B.R., Zhang, G., Iodine binding property of a ternary complex consisting of starch, protein, and free fatty acids. Carbohydr. Polym. 75 (2009), 351–355.
30. [30] Bhopatkar, D., Feng, T., Chen, F., Zhang, G., Carignano, M., Park, S.H., et al. Self-assembled nanoparticle of common food constituents that carries a sparingly soluble small molecule. J. Agric. Food Chem., 63, 2015.
31. [31] Jafari, S.M., He, Y., Bhandari, B., Encapsulation of nanoparticles of d-limonene by spray drying: role of Emulsifiers and Emulsifying Techniques. Dry. Technol.: Int. J. 25 (2007), 1069–1079.
32. [32] Shin, G.H., Chung, S.K., Kim, J.T., Joung, H.J., Park, H.J., Preparation of chitosan-coated nanoliposomes for improving the mucoadhesive property of curcumin using the ethanol injection method. J. Agric. Food Chem. 61 (2013), 11119–11126.
33. [33] Chen, T., Zhang, Y., Abbas, S., Feng, B., Zhang, X., Xia, S., Modulation of the carotenoid bioaccessibility through liposomal encapsulation. Colloids Surf. B Biointerfaces 123 (2014), 692–700.
34. [34] Pai, D.A., Vangala, V.R., Ng, J.W., Ng, W.K., Tan, R.B.H., Resistant maltodextrin as a shell material for encapsulation of naringin: production and physicochemical characterization. J. Food Eng. 161 (2015), 68–74.
35. [35] Wang, Y., Lu, Z., Wu, H., Lv, F., Study on the antibiotic activity of microcapsule curcumin against foodborne pathogens. Int. J. Food Microbiol. 136 (2009), 71–74.
36. [36] Lauro, M.R., Simone, F.D., Sansone, F., Iannelli, P., Aquino, R.P., Preparations and release characteristics of naringin and naringenin gastro-resistant microparticles by spray-drying. J. Drug Deliv. Sci. Technol. 17 (2007), 119–124.
37. [37] Hasanvand, E., Fathi, M., Bassiri, A., Javanmard, M., Abbaszadeh, R., Novel starch based nanocarrier for vitamin D fortification of milk: production and characterization. Food Bioprod. Process. 96 (2015), 264–277.
38. [38] Li, J., Shin, G.H., Lee, I.W., Chen, X., Park, H.J., Soluble starch formulated nanocomposite increases water solubility and stability of curcumin. Food Hydrocoll. 56 (2016), 41–49.
39. [39] Kizil, R., Irudayaraj, J., Seetharaman, K., Characterization of irradiated starches by using FT-Raman and FTIR spectroscopy. J. Agric. Food Chem. 50 (2002), 3912–3918.
40. [40] Yu, H., Huang, Q., Enhanced in vitro anti-cancer activity of curcumin encapsulated in hydrophobically modified starch. Food Chem. 119 (2010), 669–674.
41. [41] Zhang, G., Maladen, M., Campanella, O.H., Hamaker, B.R., Free fatty acids electronically bridge the self-assembly of a three-component nanocomplex consisting of amylose, protein, and free fatty acids. J. Agric. Food Chem., 58, 2010, 9164.
42. [42] Liu, H., Chaudhary, D., John, J., Tadé, M.O., Morphological investigation into starch bio-nanocomposites via synchrotron radiation and differential scanning calorimetry. J. Nanotechnol. 2011 (2011), 924582.1–924582.14.
43. [43] Bilensoy, E., Çırpanlı, Y., Şen, M., Doğan, A.L., Çalış, S., Thermosensitive mucoadhesive gel formulation loaded with 5-Fu: cyclodextrin complex for HPV-induced cervical cancer. J. Incl. Phenom. 57 (2007), 363–370.
44. [44] Calderini, A., Pessine, F.B.T., Synthesis and characterization of inclusion complex of the vasodilator drug minoxidil with β-cyclodextrin. J. Incl. Phenom. 60 (2008), 369–377.
45. [45] Cevher, E., Sensoy, Demet, Zloh, M., Mülaz, L., Preparation and characterisation of natamycin: γ-cyclodextrin inclusion complex and its evaluation in vaginal mucoadhesive formulations. J. Pharm. Sci. 97 (2008), 4319–4335.
46. [46] Prota, L., Santoro, A., Bifulco, M., Aquino, R.P., Mencherini, T., Russo, P., Leucine enhances aerosol performance of naringin dry powder and its activity on cystic fibrosis airway epithelial cells. Int. J. Pharm. 412 (2011), 8–19.
47. [47] Cui, L., Zhang, Z.H., Sun, E., Jia, X.B., Effect of ß-cyclodextrin complexation on solubility and enzymatic conversion of naringin. Int. J. Mol. Sci. 13 (2012), 14251–14261.
48. [48] Na, K., Park, K.H., Kim, S.W., Bae, Y.H., Self-assembled hydrogel nanoparticles from curdlan derivatives: characterization, anti-cancer drug release and interaction with a hepatoma cell line (HepG2). J. Controlled Release, 69, 2000, 225.
49. ®; E PO solid dispersion: a simple and potent method to solve the problems of curcumin. Eur. J. Pharm. Biopharm. Off. J. Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E V 94 (2015), 322–332.
50. [50] Li, J., Shin, G.H., Chen, X., Park, H.J., Modified curcumin with hyaluronic acid: combination of pro-drug and nano-micelle strategy to address the curcumin challenge. Food Res. Int. 69 (2015), 202–208.
51. [51] Zhang, G., Hamaker, B.R., Starch-free fatty acid complexation in the presence of whey protein. Carbohydr. Polym. 55 (2004), 419–424.
52. [52] Jiang, J., Zhang, X., Sun, P., Zhang L. ZnO/BiOI heterostructures: photoinduced charge-transfer property and enhanced visible-light photocatalytic activity. J. Phys. Chem. C 115 (2011), 20555–20564.
53. [53] Wang, J., Ma, W., Tu, P., The mechanism of self-assembled mixed micelles in improving curcumin oral absorption: in vitro and in vivo. Colloids Surf. B Biointerfaces 133 (2015), 108–119.
54. [54] Tan, C., Xie, J., Zhang, X., Cai, J., Xia, S., Polysaccharide-based nanoparticles by chitosan and gum arabic polyelectrolyte complexation as carriers for curcumin. Food Hydrocoll. 57 (2016), 236–245.
55. [55] Andrieux, K., Forte, L., Lesieur, S., Paternostre, M., Ollivon, M., Grabielle-Madelmont, C., Solubilisation of dipalmitoylphosphatidylcholine bilayers by sodium taurocholate: a model to study the stability of liposomes in the gastrointestinal tract and their mechanism of interaction with a model bile salt. Eur. J. Pharm. Biopharm. Off. J. Arbeitsgemeinschaft Fur Pharmazeutische Verfahrenstechnik E V 71 (2009), 346–355.
56. [56] Nykänen, P., Lempää, S., Aaltonen, M.L., Jürjenson, H., Veski, P., Marvola, M., Citric acid as excipient in multiple-unit enteric-coated tablets for targeting drugs on the colon. Int. J. Pharm. 229 (2001), 155–162.
57. [57] Milojevic, S., Newton, J.M., Cummings, J.H., Gibson, G.R., Botham, R.L., Ring, S.G., et al. Amylose as a coating for drug delivery to the colon: preparation and in vitro evaluation using glucose pellets. J. Controlled Release 38 (1996), 85–94.
58. [58] Zhang, L., Cheng, H., Zheng, C., Dong, F., Man, S., Dai, Y., et al. Structural and release properties of amylose inclusion complexes with ibuprofen. J. Drug Deliv. Sci. Technol. 31 (2015), 101–107.
59. [59] Dimantov, A., Greenberg, M., Kesselman, E., Shimoni, E., Study of high amylose corn starch as food grade enteric coating in a microcapsule model system. Innov. Food Sci. Emerg. Technol. 5 (2004), 93–100.