Polyphenols and Their Formulations: Different Strategies to Overcome the Drawbacks Associated with Their Poor Stability and Bioavailability

Polyphenols in Human Health and Disease

Volumn 1, Issue , 2013, Pages 29-45

  Parisi, Ortensia Ilaria ^a   Puoci, Francesco ^a   Restuccia, Donatella ^a   Farina, Grazia ^b   Iemma, Francesca ^a   Picci, Nevio ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

^b Aptuit Inc   (United States)

Author keywords

Bioavailability; Encapsulation; Polyphenols; Stability; Water solubility

Indexed keywords

EID: 84902572207     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-398456-2.00004-9     Document Type: Chapter

References (99)

1. Vinson J.A., Su X., Zubik L., Bose P. Phenol antioxidant quantity and quality in foods: fruits. J Agric Food Chem 2001, 49(11):5315-5321.
2. Landete J.M. Updated knowledge about polyphenols: functions, bioavailability, metabolism, and health. Crit Rev Food Sci 2012, 52(10):936-948.
3. Dehkharghanian M., Lacroix M., Vijayalakshmi M.A. Antioxidant properties of green tea polyphenols encapsulated in caseinate beads. Dairy Sci Techno 2009, 89(5):485-499.
4. Nichols J.A., Katiyar S.K. Skin photoprotection by natural polyphenols: anti-inflammatory, antioxidant and DNA repair mechanisms. Arch Dermatol Re 2010, 302(2):71-73.
5. Zern T.L., Fernandez M.L. Cardioprotective effects of dietary polyphenols. J Nutr 2005, 135(10):2291-2294.
6. Aquilano K., Baldelli S., Rotilio G., Ciriolo M.R. Role of nitric oxide synthase in Parkinson's disease: a review on the antioxidant and anti-inflammatory activity of polyphenols. Neurochem Res 2008, 33(12):2416-2426.
7. Balu M., Sangeetha P., Haripriya D., Panneerselvam C. Rejuvenation of antioxidant system in central nervous system of aged rats by grape seed extract. Neurosci Lett 2005, 383(3):295-300.
8. Baydar N.G., Sagdic O., Ozkan G., Cetin S. Determination of antibacterial effects and total phenolic contents of grape (Vitis vinifera) seed extracts. Int J Food Sci 2006, 41(7):799-804.
9. Jung H.J., Hwang I.A., Sung W.S., Kang H., Kang B.S., Seu Y.B., et al. Fungicidal effect of resveratrol on human infectious fungi. Arch Pharm Res 2005, 28(5):557-560.
10. de Bruyne T., Pieters L., Witvrouw M., de Clercq E., Berghe D.V., Vlietinck A.J. Biological evaluation of proanthocyanidin dimers and related polyphenols. J Nat Prod 1999, 62(7):954-958.
11. Chávez J.H., Leal P.C., Yunes R.A., Nunes R.J., Barardi C.R.M., Pinto A.R., et al. Evaluation of antiviral activity of phenolic compounds and derivatives against rabies virus. Vet Microbiol 2006, 116(1-3):53-59.
12. Hudson T.S., Hartle D.K., Hursting S.D., Nunez N.P., Wang T.T.Y., Young H.A., et al. Inhibition of prostate cancer growth by muscadine grape skin extract and resveratrol through distinct mechanisms. Cancer Res 2007, 67(17):8396-8405.
13. Lazzè M.C., Pizzala R., Pecharromán F.J.G., Garnica P.G., Rodriguez J.M.A., Fabris N., et al. Grape waste extract obtained by supercritical fluid extraction contains bioactive antioxidant molecules and induces antiproliferative effects in human colon adenocarcinoma cells. J Med Food 2009, 12(3):561-568.
14. Gamet-Payrastre L., Manenti S., Gratacap M.P., Tulliez J., Chap H., Payrastre B. Flavonoids and the inhibition of PKC and PI 3-kinase. Gen Pharmacol 1999, 32(3):279-286.
15. Richard T., Lefeuvre D., Descendit A., Quideau S., Monti J.P. Recognition characters in peptide-polyphenol complex formation. Biochim Biophys Acta 2006, 1760(6):951-958.
16. Xia E.-Q., Deng G.-F., Guo Y.-J., Li H.-B. Biological activities of polyphenols from grapes. Int J Mol Sci 2010, 11(2):622-646.
17. Desai K.G.H., Park H.J. Recent developments in microencapsulation of food ingredients. Dry Technol 2005, 23(7):1361-1394.
18. Picot A., Lacroix C. Production of multiphase water-insoluble microcapsules for cell microencapsulation using an emulsification/spray-drying technology. J Food Sci 2003, 68(9):2693-2700.
19. Munin A., Edwards-Lévy F. Encapsulation of natural polyphenolic compounds; a review. Pharmaceutics 2011, 3(4):793-829.
20. Gharsallaoui A., Roudaut G., Chambin O., Voilley A., Saurel R. Applications of spraydrying in microencapsulation of food ingredients: an overview. Food Res Int 2007, 40(9):1107-1121.
21. Sun-Waterhouse D., Wadhwa S.S., Waterhouse G.I.N. Spray-drying microencapsulation of polyphenol bioactives: a comparative study using different natural fibre polymers as encapsulants. Food Bioprocess Technol 2012, doi:10.1007/s11947-012-0946-y.
22. Gibbs B.F., Kermash S., Alli I., Mulligan C.N. Encapsulation in the food industry: a review. Int J Food Sci Nutr 1999, 50(3):213-224.
23. Roberfroid M.B., Delzenne N.M. Dietary fructans. Annu Rev Nutr 1998, 18:117-143.
24. Makris D.P., Boskou G., Andrikopoulos N.K. Recovery of antioxidant phenolics from white vinification solid by-products employing water/ethanol mixtures. Bioresource Technol 2007, 98(15):2963-2967.
25. Davidov-Pardo G., Arozarena I., Marín-Arroyo M.R. Optimization of a wall material formulation to microencapsulate a grape seed extract using a mixture design of experiments. Food Bioprocess Technol 2013, 6(4):941-951.
26. Haidong L., Fang Y., Zhihong T., Huanwei S., Tiehui Z. Use of combinations of gum arabic, maltodextrin and soybean protein to microencapsulate ginkgo leaf extracts and its inhibitory effect on skeletal muscle injury. Carbohyd Polym 2012, 88(2):435-440.
27. Fang Z., Bhandari B. Effect of spray drying and storage on the stability of bayberry polyphenols. Food Chem 2011, 129(3):1139-1147.
28. Bakowska-Barczak A.M., Kolodziejczyk P.P. Black currant polyphenols: their storage stability and microencapsulation. Ind Crop Prod 2011, 34(2):1301-1309.
29. Moyer R., Hummer K., Finn C., Frei B., Wrolstad R.E. Anthocyanins phenolics, and antioxidant capacity of diverse small fruits: Vaccinium, Ribes and Rubus. J Agric Food Chem 2002, 50(3):519-525.
30. Cocero M.J., Martín A., Mattea F., Varona S. Encapsulation and co-precipitation processes with supercritical fluids: fundamentals and applications. J Supercrit. Fluids 2009, 47(3):546-555.
31. Visentin A., Rodríguez-Rojo S., Navarrete A., Maestri D., Cocero M.J. Precipitation and encapsulation of rosemary antioxidants by supercritical antisolvent process. J Food Eng 2012, 109(1):9-15.
32. Escobar-Chávez J.J., López-Cervantes M., Naïk A., Kalia Y.N., Quintanar-Guerrero D., Ganem-Quintanar A. Applications of thermoreversible Pluronic F-127 gels in pharmaceutical formulations. J Pharm Pharmaceut Sci 2006, 9(3):339-358.
33. Gouin S. Microencapsulation: industrial appraisal of existing technologies and trends. Trends Food Sci Tech 2004, 15(7-8):330-347.
34. Xiong S., Melton L.D., Easteal A.J., Siew D. Stability and antioxidant activity of black currant anthocyanins in solution and encapsulated in glucan gel. J Agric Food Chem 2006, 54(17):6201-6208.
35. Deladino L., Anbinder P.S., Navarro A.S., Martino M.N. Encapsulation of natural antioxidants extracted from Ilex paraguariensis. Carbohydr Polym 2008, 71(1):126-134.
36. Ghisalberti E.L. Propolis: a review. Bee World 1979, 60:59-74.
37. Alencar S.M., Oldoni T.L.C., Castro M.L., Cabral I.S.R., Costa-Neto C.M., Cury J.A., et al. Chemical composition and biological activity of a new type of Brazilian propolis: red propolis. J Ethnopharmacol 2007, 113(2):278-283.
38. Bankova V., Popov S., Marekov N.L. Isopentenyl cinnamates from poplar buds and propolis. Phytochemistry 1989, 28(3):871-973.
39. Aso K., Kanno S.I., Tadano T., Satoh S., Ishikawa M. Inhibitory effect of propolis on the growth of human leukemia U937. Biol Pharm Bull 2004, 27(5):727-730.
40. Burdock G.A. Review of the biological properties and toxicity of bee propolis. Food Chem Toxicol 1998, 36(4):347-363.
41. Nori M.P., Favaro-Trindade C.S., Matias de Alencar S., Thomazini M., de Camargo Balieiro J., Contreras Castillo C.J. Microencapsulation of propolis extract by complex coacervation. LWT - Food Sci Technol 2011, 44(2):429-435.
42. Vandamme T.F., Poncelet D., Subra-Paternault P. Microencapsulation: des Sciences aux Technologies 2007, Lavoisier Tec & Doc, Paris, France.
43. Grant G.T., Morris E.R., Rees D.A., Smith P.J.C., Thom D. Biological interactions between polysaccharides and divalent cations: the egg box model. FEBS Lett 1973, 32(1):195-198.
44. Liang J., Li F., Fang Y., Yang W., An X., Zhao L., et al. Synthesis, characterization and cytotoxicity studies of chitosan-coated tea polyphenols nanoparticles. Coll Surf B Biointerf 2011, 82(2):297-301.
45. Chan E.-S., Yim Z.-H., Phan S.-H., Mansa R.F., Ravindra P. Encapsulation of herbal aqueous extract through absorption with ca-alginate hydrogel beads. Food Bioprod Process 2010, 88(2-3):195-201.
46. Mizugaki M., Ishizawa F., Yamazaki T., Hishinuma T. Methodological considerations for characterizing potential antioxidant actions of bioactive components in plant foods. Mutation Res 2003, 523-524:9-20.
47. Dube A., Ng K., Nicolazzo J.A., Larson I. Effective use of reducing agents and nanoparticle encapsulation in stabilizing catechins in alkaline solution. Food Chem 2010, 122(3):662-667.
48. Friberg S., Larsson K., Sjoblom J. Food Emulsions 2004, Marcel Dekker, New York. 4th ed.
49. Sessa M., Casazza A.A., Perego P., Tsao R., Ferrari G., Donsì F. Exploitation of polyphenolic extracts from grape marc as natural antioxidants by encapsulation in lipid-based nanodelivery systems. Food Bioprocess Technol 2012, doi:10.1007/s11947-012-0911-9.
50. Almajano M.P., Carbó R., Jiménez J.A.L., Gordon M.H. Antioxidant and antimicrobial activities of tea infusions. Food Chem 2008, 108(1):55-63.
51. Barras A., Mezzetti A., Richard A., Lazzaroni S., Roux S., Melnyk P., et al. Formulation and characterization of polyphenol-loaded lipid nanocapsules. Int J Pharmaceut 2009, 379(2):270-277.
52. Arshady R. Preparation of biodegradable microspheres and microcapsules: 2. Polylactides and related polyesters. J Control Release 1991, 17:1-21.
53. Wischke C., Schwendeman S.P. Principles of encapsulating hydrophobic drugs in PLA/PLGA microparticles. Int J Pharm 2008, 364(2):298-327.
54. Shahani K., Panyam J. Highly loaded, sustained-release microparticles of curcumin for chemoprevention. J Pharm Sci 2011, 100(7):2599-2609.
55. Gusman J., Malonne H., Atassi G. A reappraisal of the potential chemopreventive and chemotherapeutic properties of resveratrol. Carcinogenesis 2001, 22(8):1111-1117.
56. Joe A.K., Liu H., Suzui M., Vural M.E., Xiao D., Weinstein I.B. Resveratrol induces growth inhibition, S-phase arrest, apoptosis, and changes in biomarker expression in several human cancer cell lines. Clin. Cancer Res 2002, 8(3):893-903.
57. Kuwajerwala N., Cifuentes E., Gautam S., Menon M., Barrack E.R., VeerReddy G.P. Resveratrol induces prostate cancer cell entry into S phase and inhibits DNA synthesis. Cancer Res 2002, 62(9):2488-2492.
58. Shao J., Li X., Lu X., Jiang C., Hu Y., Li Q., et al. Enhanced growth inhibition effect of resveratrol incorporated into biodegradable nanoparticles against glioma cells is mediated by the induction of intracellular reactive oxygen species levels. Coll Surf B Biointerf 2009, 72(1):40-47.
59. Cabane E., Zhang X., Langowska K., Palivan C.G., Meier W. Stimuli-responsive polymers and their applications in nanomedicine. Biointerphases 2012, 7(1-4):1-27.
60. Lin Q.L., Wang J., Qin D., Björn B. Influence of amphiphilic structures on the stability of polyphenols with different hydrophobicity. Sci China Ser B-Chem 2007, 50(1):121-126.
61. Lu Q., Li D.-C., Jiang J.-G. Preparation of a tea polyphenol nanoliposome system and Its physicochemical properties. J Agric Food Chem 2011, 59(24):13004-13011.
62. Caddeo C., Teskač K., Sinico C., Kristl J. Effect of resveratrol incorporated in liposomes on proliferation and UV-B protection of cells. Int J Pharmaceut 2008, 363(1-2):183-191.
63. Bernardy N., Romio A.P., Barcelos E.I., Pizzol C.D., Dora C.L., Lemos-Senna E., et al. Nanoencapsulation of quercetin via miniemulsion polymerization. J Biomed NanoTechnol 2010, 6(2):181-186.
64. Pagington J.S. α-Cyclodextrin and its uses in the flavour industry. Developments in Food Flavours 1986, Elsevier Applied Science, London. G.G. Birch, M.G. Lindley (Eds.).
65. Zhou J., Ritter H. Cyclodextrin functionalized polymers as drug delivery systems. Polym Chem 2010, 1:1552-1559.
66. López-Tobar E., Blanch G.P., Ruiz del Castillo M.L., Sanchez-Cortes S. Encapsulation and isomerization of curcumin with cyclodextrins characterized by electronic and vibrational spectroscopy. Vib Spectrosc 2012, 62:292-298.
67. Anselmi C., Centini M., Maggiore M., Gaggelli N., Andreassi M., Buonocore A., et al. Non-covalent inclusion of ferulic acid with α-cyclodextrin improves photo-stability and delivery: NMR and modeling studies. J Pharm Biomed Anal 2008, 46(4):645-652.
68. Oetjen G.-W., Haseley P. Freeze-drying 2004, Wiley-VCH Verlag Gmbh & Co. KGaA, Weinheim.
69. Delgado-Vargas F., Jimenez A.R., Pardes-Lopez O. Natural pigments: carotenoids, anthocyanins and betalains - characteristics, biosynthesis, processing and stability. Crit Rev Food Sci Nutr 2000, 40(3):173-289.
70. Laine P., Kylli P., Heinonen M., Jouppila K. Storage stability of microencapsulated cloudberry (Rubus chamaemorus) phenolics. J Agric Food Chem 2008, 56(23):11251-11261.
71. 4-induced hepatic injury and fibrosis through reduction of pro-inflammatory cytokines and stellate cell activation. Lab Invest 2011, 91(9):1383-1395.
72. Parisi O.I., Puoci F., Iemma F., Curcio M., Cirilli G., Spizzirri U.G., et al. Flavonoids preservation and release by methacrylic acid-grafted (N-vinyl-pyrrolidone). Pharm Dev Technol 2013, 18(5):1058-1065.
73. Tita B., Fulias A., Bandur G., Marian E., Tita D. Compatibility study between ketoprofen and pharmaceutical excipients used in solid dosage forms. J Pharm Biomed Anal 2011, 56(2):221-227.
74. Kivikero N., Murtomaa M., Antikainen O., Hatara J., Juppo A.M., Sandler N. Rapid formulation screening with a multipart microscale fluid bed powder processor. Pharm Dev Technol 2011, 16(4):358-366.
75. Cirillo G., Puoci F., Iemma F., Curcio M., Parisi O.I., Spizzirri U.G., et al. Starch-quercetin conjugate by radical grafting: synthesis and biological characterization. Pharm Dev Technol 2011, 17(4):466-476.
76. Landete J.M. Updated knowledge about polyphenols: functions, bioavailability, metabolism, and health. Crit Rev Food Sci Nutr 2012, 52(10):936-948.
77. Karakaya S. Biovailability of phenolic compounds. Crit Rev Food Sci Nutr 2004, 44(6):453-464.
78. Semalty A., Semalty M., Rawat M.S.M., Franceschi F. Supramolecular phospholipids-polyphenolics interactions: the PHYTOSOME® strategy to improve the bioavailability of phytochemicals. Fitoterapia 2010, 81(5):306-314.
79. Muqbil I., Masood A., Sarkar F.H., Mohammad R.M., Azmi A.S. Progress in nanotechnology based approaches to enhance the potential of chemopreventive agents. Cancers 2011, 3(1):428-445.
80. Lambert J.D., Yang C.S. Cancer chemopreventive activity and bioavailability of tea and tea polyphenols. Mutat Res 2003, 523-524:727-747.
81. Chen Z., Zhu Q.Y., Tsang D., Huang Y. Degradation of green tea catechins in tea drinks. J Agric Food Chem 2001, 49(1):477-482.
82. Lu H., Meng X., Yang C.S. Enzymology of methylation of tea catechins and inhibition of catechol-O-methyltransferase by (-)-epigallocatechin gallate. Drug Metab Dispos 2003, 31(5):572-579.
83. Smith A., Giunta B., Bickford P.C., Fountain M., Tan J., Shytle R.D. Nanolipidic particles improve the bioavailability and α-secretase inducing ability of epigallocatechin-3-gallate (EGCG) for the treatment of Alzheimer's disease. Int J Pharmaceut 2010, 389(1-2):207-212.
84. Pan M.H., Huang T.M., Lin J.K. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab Dispos 1999, 27(4):486-494.
85. Soleas G.J., Yan J., Goldberg D.M. Measurement of trans-resveratrol, (+)-catechin, and quercetin in rat and human blood and urine by gas chromatography with mass selective detection. Methods Enzymol 2001, 335:130-145.
86. Narayanan N.K., Nargi D., Randolph C., Narayanan B.A. Liposome encapsulation of curcumin and resveratrol in combination reduces prostate cancer incidence in PTEN knockout mice. Int J Cancer 2009, 125(1):1-8.
87. Clifford M.N. Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden. J Agric Food Chem 1999, 79(3):362-372.
88. Çelik S.E., Tufan A.N., Ozyurek M., Güçlü K., Apak R. Spectroscopic study and antioxidant properties of the inclusion complexes of rosmarinic acid with natural and derivative cyclodextrins. Spectrochimica Acta Part A 2011, 78(5):1615-1624.
89. Esmaili M., Ghaffari S.M., Moosavi-Movahedi Z., Atri A., Sharifizadeh, Farhadi M., et al. Beta casein-micelle as a nano vehicle for solubility enhancement of curcumin; food industry application. LWT - Food Sci Technol 2011, 44(10):2166-2172.
90. Lu Z., Cheng B., Hu Y., Zhang Y., Zou G. Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity. Food Chem 2009, 113(1):17-20.
91. Atanacković M., Poŝša M., Heinle H., Gojković-Bukarica L., Cvejić J. Solubilization of resveratrol in micellar solutions of different bile acids. Col Surf B: Biointerfaces 2009, 72(1):148-154.
92. Ma Z., Haddadi A., Molavi O., Lavasanifar A., Lai R., Samuel J. Micelles of poly(ethylene oxide)-b-poly(ε-caprolactone) as vehicles for the solubilization, stabilization, and controlled delivery of curcumin. J Biomed Mater Res A 2008, 86(2):300-310.
93. Paramera E.I., Konteles S.J., Karathanos V.T. Stability and release properties of curcumin encapsulated in Saccharomyces cerevisiae, β-cyclodextrin and modified starch. Food Chem 2011, 125(3):913-922.
94. Walle T. Absorption and metabolim of flavonoids. Free Radic Biol Med 2004, 36(7):829-837.
95. Rechner A.R., Smith M.A., Kuhnle G., Gibson G.R., Debnam E.S., Srai S.K., et al. Colonic metabolim of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic Biol Med 2004, 36(2):212-225.
96. Selma M.V., Espin J.C., Tomás-Barberan F.A. Interaction between phenolics and gut microbiota role in human health. J Agric Food Chem 2009, 57(15):6485-6501.
97. Aziz M.H., Kumar R., Ahmad N. Cancer chemoprevention by resveratrol: in vitro and in vivo studies and the underlying mechanisms (review). Int J Oncol 2003, 23(1):17-28.
98. Bonechi C., Martini S., Ciani L., Lamponi S., Rebmann H., Rossi C., et al. Using liposomes as carriers for polyphenolic compounds: the case of trans-resveratrol. PLoS ONE 2012, 7(8):e41438.
99. Shahani K., Swaminathan S.K., Freeman D., Blum A., Ma L., Panyam J. Injectable sustained release microparticles of curcumin: a new concept for cancer chemoprevention. Cancer Res 2010, 70(11):4443-4452.