Skip to main content
SpringerLink
Log in
Book cover

Bioactive Molecules in Food pp 1–18Cite as

Bound Phenolics in Foods

  • Living reference work entry
  • First Online:

Part of the book series: Reference Series in Phytochemistry ((RSP))

Abstract

Bound phenolic compounds are widely distributed among several plants, especially cereals. In most of the cases, covalent bonds are formed with polysaccharides, proteins, or lipids. But additionally, hydrophobic interactions may affect their release from the food matrix. Many studies have reported their bioactivity after their release from foods, in most of the cases involving acid or basic hydrolysis and further extraction with organic solvents. Besides their antioxidant activity, bound phenolics have important effects on the inhibition of cancer cell growth, key enzymes involved in the metabolism of carbohydrates, as well as in the regulation of inflammatory processes. Food processing and gastrointestinal digestion affect the bound phenolic bioavailability and in consequence the potential benefits to human health. Recent studies have demonstrated that microbiota composition in the gastrointestinal tract affect the release of bound phenolics and their metabolism. Therefore future studies will help us to understand the complex interactions between bound phenolics and gastrointestinal microbiota and produce natural controlled released bioactive phenolic compounds.

This is a preview of subscription content, log in via an institution.

References

  1. Tomás-Barberán FA, Espín JC (2001) Phenolic compounds and related enzymes as determinants of quality in fruits and vegetables. J Sci Food Agric 81:853–876. https://doi.org/10.1002/jsfa.885

    Article  Google Scholar 

  2. Mandal SM, Chakraborty D, Dey S (2010) Phenolic acids act as signaling molecules in plant-microbe symbioses. Plant Signal Behav 5:359–368. https://doi.org/10.4161/psb.5.4.10871

    Article  CAS  Google Scholar 

  3. Tsao R, Rong (2010) Chemistry and biochemistry of dietary polyphenols. Nutrients 2:1231–1246. https://doi.org/10.3390/nu2121231

    Article  CAS  Google Scholar 

  4. Reis Giada MdeL (2013) Food phenolic compounds: main classes, sources and their antioxidant power. In: Oxidative stress and chronic degenerative diseases- a role for antioxidants. pp 87–112

    Google Scholar 

  5. Goufo P, Trindade H (2014) Rice antioxidants: phenolic acids, flavonoids, anthocyanins, proanthocyanidins, tocopherols, tocotrienols, γ -oryzanol, and phytic acid. Food Sci Nutr 2:75–104. https://doi.org/10.1002/fsn3.86

    Article  CAS  Google Scholar 

  6. Ayoub M, De Camargo AC, Shahidi F (2016) Antioxidants and bioactivities of free, esterified and insoluble-bound phenolics from berry seed meals. Food Chem 197:221–232. https://doi.org/10.1016/j.foodchem.2015.10.107

    Article  CAS  Google Scholar 

  7. Girgin N, El SN (2015) Effects of cooking on in vitro sinigrin bioaccessibility, total phenols, antioxidant and antimutagenic activity of cauliflower (Brassica oleraceae L. var. Botrytis). J Food Compos Anal 37:119–127. https://doi.org/10.1016/J.JFCA.2014.04.013

    Article  CAS  Google Scholar 

  8. Karimi A, Mohammadi-Kamalabadi M, Rafieian-Kopaei M et al (2016) Determination of antioxidant activity, phenolic contents and antiviral potential of methanol extract of Euphorbia spinidens Bornm (Euphorbiaceae). Trop J Pharm Res 15:759. https://doi.org/10.4314/tjpr.v15i4.13

    Article  Google Scholar 

  9. Luo J, Zhang P, Li S, Shah NP (2016) Antioxidant, antibacterial, and antiproliferative activities of free and bound phenolics from peel and flesh of Fuji apple. J Food Sci 81:M1735–M1742. https://doi.org/10.1111/1750-3841.13353

    Article  CAS  Google Scholar 

  10. Mushtaq M, Sultana B, Anwar F, Batool S (2015) Antimutagenic and antioxidant potential of aqueous and acidified methanol extracts from Citrus limonum fruit residues. J Chil Chem Soc 60:2979–2983. https://doi.org/10.4067/S0717-97072015000200025

    Article  CAS  Google Scholar 

  11. Acosta-Estrada BA, Gutiérrez-Uribe JA, Serna-Saldívar SO (2014) Bound phenolics in foods, a review. Food Chem 152:46–55. https://doi.org/10.1016/j.foodchem.2013.11.093

    Article  CAS  Google Scholar 

  12. Le Bourvellec C, Renard CMGC (2012) Interactions between polyphenols and macromolecules: quantification methods and mechanisms. Crit Rev Food Sci Nutr 52:213–248. https://doi.org/10.1080/10408398.2010.499808

    Article  Google Scholar 

  13. Shahidi F, Yeo JD (2016) Insoluble-bound phenolics in food. Molecules 21. https://doi.org/10.3390/molecules21091216

  14. Alu’datt MH, Rababah T, Alhamad MN et al (2017) Occurrence, types, properties and interactions of phenolic compounds with other food constituents in oil-bearing plants. Crit Rev Food Sci Nutr:1–10. https://doi.org/10.1080/10408398.2017.1391169

  15. Li M, Koecher K, Hansen L, Ferruzzi MG (2017) Phenolics from whole grain oat products as modifiers of starch digestion and intestinal glucose transport. J Agric Food Chem 65:6831–6839. https://doi.org/10.1021/acs.jafc.7b02171

    Article  CAS  Google Scholar 

  16. Buitimea-Cantúa NE, Gutiérrez-Uribe JA, Serna-Saldívar SO (2017) Phenolic–protein interactions: Effects on food properties and health benefits. J Med Food 0:jmf.2017.0057. https://doi.org/10.1089/jmf.2017.0057

  17. He T, Liang Q, Luo T, Wang Y, Luo G (2010) Study on interactions of phenolic acid-like drug candidates with bovine serum albumin by capillary electrophoresis and fluorescence spectroscopy. J Solut Chem 39:1653–1664. https://doi.org/10.1007/s10953-010-9608-8

    Article  CAS  Google Scholar 

  18. Li S, Huang K, Zhong M, Guo J, Wang WZ, Zhu R (2010) Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin. Spectrochim Acta Part A Mol Biomol Spectrosc 77:680–686. https://doi.org/10.1016/J.SAA.2010.04.026

    Article  Google Scholar 

  19. Skrt M, Benedik E, Podlipnik Č, Ulrih NP (2012) Interactions of different polyphenols with bovine serum albumin using fluorescence quenching and molecular docking. Food Chem 135:2418–2424. https://doi.org/10.1016/J.FOODCHEM.2012.06.114

    Article  CAS  Google Scholar 

  20. Ropiak HM, Lachmann P, Ramsay A, Green RJ, Mueller-Harvey I (2017) Identification of structural features of condensed tannins that affect protein aggregation. PLoS One 12:e0170768. https://doi.org/10.1371/journal.pone.0170768

    Article  Google Scholar 

  21. Cong-Cong X, Bing W, Yi-Qiong P, Jian-Sheng T, Zhang T (2017) Advances in extraction and analysis of phenolic compounds from plant materials. Chin J Nat Med 15:721–731. https://doi.org/10.1016/S1875-5364(17)30103-6

    Google Scholar 

  22. Yeo J, Shahidi F (2017) Effect of hydrothermal processing on changes of insoluble-bound phenolics of lentils. J Funct Foods 38:716–722. https://doi.org/10.1016/J.JFF.2016.12.010

    Article  CAS  Google Scholar 

  23. Manach C, Scalbert A, Morand C, Rémésy C, Jiménez L (2004) Polyphenols: food sources and bioavailability. Am J Clin Nutr 79:727–747. https://doi.org/10.1038/nature05488

    Article  CAS  Google Scholar 

  24. Adom KK, Liu RH (2002) Antioxidant activity of grains. J Agric Food Chem 50:6182–6187. https://doi.org/10.1021/jf0205099

    Article  CAS  Google Scholar 

  25. Zhu Y, Li T, Fu X, Abbasi AM, Zheng B, Liu RH (2015) Phenolics content, antioxidant and antiproliferative activities of dehulled highland barley (Hordeum vulgare L.) J Funct Foods 19:439–450. https://doi.org/10.1016/j.jff.2015.09.053

    Article  CAS  Google Scholar 

  26. Rohn S, Rawel HM, Kroll J (2004) Antioxidant activity of protein-bound quercetin. J Agric Food Chem 52:4725–4729. https://doi.org/10.1021/JF0496797

    Article  CAS  Google Scholar 

  27. Rao RSP, Muralikrishna G (2006) Water soluble feruloyl arabinoxylans from rice and ragi: changes upon malting and their consequence on antioxidant activity. Phytochemistry 67:91–99. https://doi.org/10.1016/J.PHYTOCHEM.2005.09.036

    Article  CAS  Google Scholar 

  28. Ayala-Soto FE, Serna-Saldívar SO, Welti-Chanes J, Gutierrez-Uribe JA (2015) Phenolic compounds, antioxidant capacity and gelling properties of glucoarabinoxylans from three types of sorghum brans. J Cereal Sci 65:277–284. https://doi.org/10.1016/j.jcs.2015.08.004

    Article  CAS  Google Scholar 

  29. Chan CL, Gan RY, Corke H (2016) The phenolic composition and antioxidant capacity of soluble and bound extracts in selected dietary spices and medicinal herbs. Int J Food Sci Technol 51:565–573. https://doi.org/10.1111/ijfs.13024

    Article  CAS  Google Scholar 

  30. Siddaraju MN, Dharmesh SM (2007) Inhibition of gastric H+,K+-ATPase and Helicobacter pylori growth by phenolic antioxidants of Zingiber officinale. Mol Nutr Food Res 51:324–332. https://doi.org/10.1002/mnfr.200600202

    Article  CAS  Google Scholar 

  31. Gordon MH, Wishart K (2010) Effects of chlorogenic acid and bovine serum albumin on the oxidative stability of low density lipoproteins in vitro. J Agric Food Chem 58:5828–5833. https://doi.org/10.1021/jf100106e

    Article  CAS  Google Scholar 

  32. Wang H, Guo X, Hu X, Li T, Fu X, Liu RH (2017) Comparison of phytochemical profiles, antioxidant and cellular antioxidant activities of different varieties of blueberry (Vaccinium spp.) Food Chem 217:773–781. https://doi.org/10.1016/j.foodchem.2016.09.002

    Article  CAS  Google Scholar 

  33. Su D, Zhang R, Hou F, Zhang M, Guo J, Huang F, Deng Y, Wei Z (2014) Comparison of the free and bound phenolic profiles and cellular antioxidant activities of litchi pulp extracts from different solvents. BMC Complement Altern Med 14:9. https://doi.org/10.1186/1472-6882-14-9

    Article  Google Scholar 

  34. Acosta-Estrada BA, Serna-Saldívar SO, Gutiérrez-Uribe JA (2015) Chemopreventive effects of feruloyl putrescines from wastewater (Nejayote) of lime-cooked white maize (Zea mays). J Cereal Sci 64:23–28. https://doi.org/10.1016/j.jcs.2015.04.012

    Article  CAS  Google Scholar 

  35. Antunes-Ricardo M, Moreno-García BE, Gutiérrez-Uribe JA, Aráiz-Hernández D, Alvarez MM, Serna-Saldivar SO (2014) Induction of apoptosis in colon cancer cells treated with isorhamnetin glycosides from Opuntia ficus-indica pads. Plant Foods Hum Nutr 69:331–336. https://doi.org/10.1007/s11130-014-0438-5

    Article  CAS  Google Scholar 

  36. Haratifar S, Meckling KA, Corredig M (2014) Antiproliferative activity of tea catechins associated with casein micelles, using HT29 colon cancer cells. J Dairy Sci 97:672–678. https://doi.org/10.3168/jds.2013-7263

    Article  CAS  Google Scholar 

  37. Shi J, Shan S, Li Z, Li H, Li X, Li Z (2015) Bound polyphenol from foxtail millet bran induces apoptosis in HCT-116 cell through ROS generation. J Funct Foods 17:958–968. https://doi.org/10.1016/J.JFF.2015.06.049

    Article  CAS  Google Scholar 

  38. Alu’datt MH, Rababah T, Alhamad MN, Al-Mahasneh MA, Ereifej K, Al-Karaki G, Al-Duais M, Andrade JE, Tranchant CC, Kubow S, Ghozlan KA (2017) Profiles of free and bound phenolics extracted from Citrus fruits and their roles in biological systems: content, and antioxidant, anti-diabetic and anti-hypertensive properties. Food Funct 8:3187–3197. https://doi.org/10.1039/C7FO00212B

    Article  Google Scholar 

  39. Pradeep PM, Sreerama YN (2017) Soluble and bound phenolics of two different millet genera and their milled fractions: comparative evaluation of antioxidant properties and inhibitory effects on starch hydrolysing enzyme activities. J Funct Foods 35:682–693. https://doi.org/10.1016/J.JFF.2017.06.033

    Article  CAS  Google Scholar 

  40. Oboh G, Ademosun AO (2011) Shaddock peels (Citrus maxima) phenolic extracts inhibit α-amylase, α-glucosidase and angiotensin I-converting enzyme activities: a nutraceutical approach to diabetes management. Diabetes Metab Syndr Clin Res Rev 5:148–152. https://doi.org/10.1016/j.dsx.2012.02.008

    Article  Google Scholar 

  41. Ademiluyi AO, Oboh G (2013) Soybean phenolic-rich extracts inhibit key-enzymes linked to type 2 diabetes (alpha-amylase and alpha-glucosidase) and hypertension (angiotensin I converting enzyme) in vitro. Exp Toxicol Pathol 65:305–309. https://doi.org/10.1016/j.etp.2011.09.005

    Article  CAS  Google Scholar 

  42. Tang Y, Zhang B, Li X, Chen PX, Zhang H, Liu R, Tsao R (2016) Bound phenolics of quinoa seeds released by acid, alkaline, and enzymatic treatments and their antioxidant and α-glucosidase and pancreatic lipase inhibitory effects. J Agric Food Chem 64:1712–1719. https://doi.org/10.1021/acs.jafc.5b05761

    Article  CAS  Google Scholar 

  43. Ademosun AO, Oboh G, Passamonti S, Tramer F, Ziberna L, Boligon AA, Athayde ML (2015) Phenolics from grapefruit peels inhibit HMG-CoA reductase and angiotensin-I converting enzyme and show antioxidative properties in endothelial EA.Hy 926 cells. Food Sci Human Wellness 4:80–85. https://doi.org/10.1016/j.fshw.2015.05.002

    Article  Google Scholar 

  44. Antunes-Ricardo M, Gutiérrez-Uribe JA, López-Pacheco F, Alvarez MM, Serna-Saldívar SO (2015) In vivo anti-inflammatory effects of isorhamnetin glycosides isolated from Opuntia ficus-indica (L.) mill cladodes. Ind Crop Prod 76:803–808. https://doi.org/10.1016/j.indcrop.2015.05.089

    Article  CAS  Google Scholar 

  45. Massaretto IL, Alves MF, de Mira NV, Carmona AK, Marquez UM (2011) Phenolic compounds in raw and cooked rice (Oryza sativa L.) and their inhibitory effect on the activity of angiotensin I-converting enzyme. J Cereal Sci 54:236–240. https://doi.org/10.1016/j.jcs.2011.06.006

    Article  CAS  Google Scholar 

  46. Shahidi F, Zhong Y (2015) Measurement of antioxidant activity. J Funct Foods 18:757–781. https://doi.org/10.1016/j.jff.2015.01.047

    Article  CAS  Google Scholar 

  47. Cömert ED, Gökmen V (2017) Antioxidants bound to an insoluble food matrix: their analysis, regeneration behavior, and physiological importance. Compr Rev Food Sci Food Saf 16:382–399. https://doi.org/10.1111/1541-4337.12263

    Article  Google Scholar 

  48. Min B, Gu L, McClung AM, Bergman CJ, Chen MH (2012) Free and bound total phenolic concentrations, antioxidant capacities, and profiles of proanthocyanidins and anthocyanins in whole grain rice (Oryza sativa L.) of different bran colours. Food Chem 133:715–722. https://doi.org/10.1016/j.foodchem.2012.01.079

    Article  CAS  Google Scholar 

  49. Ayala-Soto FE, Serna-Saldívar SO, Welti-Chanes J (2017) Effect of arabinoxylans and laccase on batter rheology and quality of yeast-leavened gluten-free bread. J Cereal Sci 73:10–17

    Article  CAS  Google Scholar 

  50. Zhang R, Zeng Q, Deng Y, Zhang M, Wei Z, Zhang Y, Tang X (2013) Phenolic profiles and antioxidant activity of litchi pulp of different cultivars cultivated in Southern China. Food Chem 136:1169–1176. https://doi.org/10.1016/j.foodchem.2012.09.085

    Article  CAS  Google Scholar 

  51. Wolfe KL, Liu RH (2007) Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. J Agric Food Chem 55:8896–8907. https://doi.org/10.1021/jf0715166

    Article  CAS  Google Scholar 

  52. Wegrzyn TF, Farr JM, Hunter DC, Au J, Wohlers MW, Skinner MA, Stanley RA (2008) Stability of antioxidants in an apple polyphenol–milk model system. Food Chem 109:310–318. https://doi.org/10.1016/J.FOODCHEM.2007.12.034

    Article  CAS  Google Scholar 

  53. Cuendet M, Oteham CP, Moon RC, Pezzuto JM (2006) Quinone reductase induction as a biomarker for chancer chemoprevention. J Nat Prod 69:460–463

    Article  CAS  Google Scholar 

  54. de Sales PM, de Souza PM, Simeoni LA, Magalhães PO, Silveira D (2012) α-amylase inhibitors: a review of raw material and isolated compounds from plant source. J Pharm Pharm Sci 15:141–183. https://doi.org/10.18433/J35S3K

    Article  Google Scholar 

  55. Kumar V, Prakash O, Kumar S, Narwal S (2011) α-glucosidase inhibitors from plants: a natural approach to treat diabetes. Pharmacogn Rev 5:19. https://doi.org/10.4103/0973-7847.79096

    Article  CAS  Google Scholar 

  56. Birari RB, Bhutani KK (2007) Pancreatic lipase inhibitors from natural sources: unexplored potential. Drug Discov Today 12. https://doi.org/10.1016/j.drudis.2007.07.024

  57. Fogliano V, Corollaro ML, Vitaglione P, Napolitano A, Ferracane R, Travaglia F, Arlorio M, Costabile A, Klinder A, Gibson G (2011) In vitro bioaccessibility and gut biotransformation of polyphenols present in the water-insoluble cocoa fraction. Mol Nutr Food Res 55:S44–S55. https://doi.org/10.1002/mnfr.201000360

    Article  CAS  Google Scholar 

  58. Papillo VA, Vitaglione P, Graziani G, Gokmen V, Fogliano V (2014) Release of antioxidant capacity from five plant foods during a multistep enzymatic digestion protocol. J Agric Food Chem 62:4119–4126. https://doi.org/10.1021/jf500695a

    Article  CAS  Google Scholar 

  59. Vitaglione P, Napolitano A, Fogliano V (2008) Cereal dietary fibre: a natural functional ingredient to deliver phenolic compounds into the gut. Trends Food Sci Technol 19:451–463. https://doi.org/10.1016/j.tifs.2008.02.005

    Article  CAS  Google Scholar 

  60. Williams BA, Grant LJ, Gidley MJ, Mikkelsen D (2017) Gut fermentation of dietary fibres: Physico-chemistry of plant cell walls and implications for health. Int J Mol Sci 18:2203

    Article  Google Scholar 

Download references

Acknowledgments

We appreciate the support from NutriOmics Chair from Tecnológico de Monterrey.

Author information

Authors and Affiliations

  1. Tecnologico de Monterrey, School of Engineering and Science, Centro de Biotecnología-FEMSA, Monterrey, Mexico

    Liliana Santos-Zea & Javier Villela-Castrejón

  2. Tecnologico de Monterrey, School of Engineering and Science, Department of Bioengineering and Science, Campus Puebla, Puebla, Mexico

    Janet A. Gutiérrez-Uribe

Authors
  1. Liliana Santos-Zea
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Javier Villela-Castrejón
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Janet A. Gutiérrez-Uribe
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Janet A. Gutiérrez-Uribe .

Editor information

Editors and Affiliations

  1. Gr. d'Etude Subst. Vég. à Act. Biol, Institut des Sciences de la Vigne e Gr. d'Etude Subst. Vég. à Act. Biol, Villenave d'Ornon, France

    Jean-Michel Mérillon

  2. M.L. Sukhadia University , Badgaon, Rajasthan, India

    K.G. Ramawat

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer International Publishing AG

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Santos-Zea, L., Villela-Castrejón, J., Gutiérrez-Uribe, J.A. (2018). Bound Phenolics in Foods. In: Mérillon, JM., Ramawat, K. (eds) Bioactive Molecules in Food. Reference Series in Phytochemistry. Springer, Cham. https://doi.org/10.1007/978-3-319-54528-8_13-1

Download citation

  • DOI: https://doi.org/10.1007/978-3-319-54528-8_13-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Cham

  • Print ISBN: 978-3-319-54528-8

  • Online ISBN: 978-3-319-54528-8

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics

Search

Navigation