Skip to main content

Health Benefits of Dietary Phenolic Compounds and Biogenic Amines

  • Living reference work entry
  • Latest version View entry history
  • First Online:
  • 603 Accesses

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

Abstract

The bioavailability of dietary phytochemicals may be influenced by several factors as food matrix, cultivation conditions, host microbiota, and physiological state. Phenolic compounds and polyamines have been associated with various health benefits. However, their role in human health is dependent on interactions with the gut microbiota and conversion to further bioactive compounds. Dietary compounds have a wide range of effects that are play after the binding and/or interaction between these compounds and other molecules.

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

Abbreviations

ADC:

Arginine decarboxylase

AIH:

Agmatine iminohydrolase

BHA:

Butylated hydroxyanisole

BHT:

Butylated hydroxytoluene

CANSpdDC:

Carboxynorspermidine decarboxylase

CANSpdDH:

Carboxynorspermidine dehydrogenase

CPA:

N-carbamoylputrescine amidohydrolase

DAO:

Diamine oxidase

DDC:

3,4-dihydroxyphenylalanine decarboxylase

DOPA:

3,4 Dihydroxyphenylalanine

E4-P:

Erythrose 4-phosphate

GABA:

γ-aminobutyric acid

HDC:

Histidine decarboxylase

ODC:

Ornithine decarboxylase

PAL:

Phenylalanine ammonia liase

PAO:

Polyamine oxidase

PEP:

Phosphoenolpyruvate

POD:

Peroxidase

PPO:

Polyphenol oxidases

ROS:

Reactive oxygen species

SAM:

S- adenosylmethionine

SAMDC:

S-adenosylmethionine decarboxylase

SAT1:

Spermidine/spermine-N1-acetyltransferase

SPDS:

Spermidine synthase

SPMS:

Spermine synthase

TAL:

Tyrosine ammonia-lyase

TGFβ:

Transforming growth factor-β

References

  1. Du G, Li M, Ma F, Liang D (2009) Antioxidant capacity and the relationship with polyphenol and vitamin C in Actinidia fruits. Food Chem 113:557–562. https://doi.org/10.1016/j.foodchem.2008.08.025

    Article  CAS  Google Scholar 

  2. Crozier A, Del Rio D, Clifford MN (2010) Bioavailability of dietary flavonoids and phenolic compounds. Mol Asp Med 31:446–467. https://doi.org/10.1016/j.mam.2010.09.007

    Article  CAS  Google Scholar 

  3. Pan M-H, Lai C-S, Ho C-T (2010) Anti-inflammatory activity of natural dietary flavonoids. Food Funct 1:15. https://doi.org/10.1039/c0fo00103a

    Article  CAS  Google Scholar 

  4. Heo HJ, Kim YJ, Chung D, Kim DO (2007) Antioxidant capacities of individual and combined phenolics in a model system. Food Chem 104:87–92. https://doi.org/10.1016/j.foodchem.2006.11.002

    Article  CAS  Google Scholar 

  5. Tzin V, Galili G (2010) The biosynthetic pathways for shikimate and aromatic amino acids in Arabidopsis thaliana. Arabidopsis Book 8:e0132. https://doi.org/10.1199/tab.0132

    Article  Google Scholar 

  6. Maeda H, Dudareva N (2012) The shikimate pathway and aromatic amino acid biosynthesis in plants. Annu Rev Plant Biol 63:73–105. https://doi.org/10.1146/annurev-arplant-042811-105439

    Article  CAS  Google Scholar 

  7. Caretto S, Linsalata V, Colella G et al (2015) Carbon fluxes between primary metabolism and phenolic pathway in plant tissues under stress. Int J Mol Sci 16:26378–26394. https://doi.org/10.3390/ijms161125967

    Article  CAS  Google Scholar 

  8. Saito K, Yonekura-Sakakibara K, Nakabayashi R et al (2013) The flavonoid biosynthetic pathway in Arabidopsis: structural and genetic diversity. Plant Physiol Biochem 72:21–34. https://doi.org/10.1016/j.plaphy.2013.02.001

    Article  CAS  Google Scholar 

  9. Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell Online 7:1085–1097. https://doi.org/10.1105/tpc.7.7.1085

    Article  CAS  Google Scholar 

  10. Zhang Z, Pang X, Xuewu D et al (2005) Role of peroxidase in anthocyanin degradation in litchi fruit pericarp. Food Chem 90:47–52. https://doi.org/10.1016/j.foodchem.2004.03.023

    Article  CAS  Google Scholar 

  11. Richard-Forget FC, Gauillard FA (1997) Oxidation of chlorogenic acid, catechins, and 4-methylcatechol in model solutions by combinations of pear (Pyrus communis Cv. Williams) polyphenol oxidase and peroxidase: a possible involvement of peroxidase in enzymatic browning. J Agric Food Chem 45:2472–2476. https://doi.org/10.1021/jf970042f

    Article  CAS  Google Scholar 

  12. Kumari P, Barman K, Patel VB et al (2015) Reducing postharvest pericarp browning and preserving health promoting compounds of litchi fruit by combination treatment of salicylic acid and chitosan. Sci Hortic 197:555–563. https://doi.org/10.1016/j.scienta.2015.10.017

    Article  CAS  Google Scholar 

  13. Barman K, Siddiqui W, Patel VB, Prasad M (2014) Nitric oxide reduces pericarp browning and preserves bioactive antioxidants in litchi. Sci Hortic 171:71–77. https://doi.org/10.1016/j.scienta.2014.03.036

    Article  CAS  Google Scholar 

  14. Ali S, Khan AS, Malik AU (2016) Postharvest l -cysteine application delayed pericarp browning, suppressed lipid peroxidation and maintained antioxidative activities of litchi fruit. Postharvest Biol Technol 121:135–142. https://doi.org/10.1016/j.postharvbio.2016.07.015

    Article  CAS  Google Scholar 

  15. Haddouche L, Phalak A, Tikekar RV (2015) Inactivation of polyphenol oxidase using 254nm ultraviolet light in a model system. LWT Food Sci Technol 62:97–103. https://doi.org/10.1016/j.lwt.2015.01.039

    Article  CAS  Google Scholar 

  16. Binh PNT, Soda K, Kawakami M (2010) Mediterranean diet and polyamine intake: possible contribution of increased polyamine intake to inhibition of age- associated disease. Nutr Diet Suppl:1. https://doi.org/10.2147/NDS.S15349

  17. Shalaby AR (1996) Significance of biogenic amines to food safety and human health. Food Res Int 29:675–690. https://doi.org/10.1016/S0963-9969(96)00066-X

    Article  CAS  Google Scholar 

  18. Maijala RL (1993) Formation of histamine and tyramine by some lactic acid bacteria in MRS- broth and modified decarboxylation agar. Lett Appl Microbiol 17:40–43. https://doi.org/10.1111/j.1472-765X.1993.tb01431.x

    Article  CAS  Google Scholar 

  19. Santos MHS (1996) Biogenic amines: their importance in foods. Int J Food Microbiol 29:213–231. https://doi.org/10.1016/0168-1605(95)00032-1

    Article  CAS  Google Scholar 

  20. Latorre-Moratalla ML, Veciana-Nogués T, Bover-Cid S et al (2008) Biogenic amines in traditional fermented sausages produced in selected European countries. Food Chem 107:912–921. https://doi.org/10.1016/j.foodchem.2007.08.046

    Article  CAS  Google Scholar 

  21. Cooke JP, Singer AH, Tsao P et al (1992) Antiatherogenic effects of L-arginine in the hypercholesterolemic rabbit. J Clin Invest 90:1168–1172. https://doi.org/10.1172/JCI115937

    Article  CAS  Google Scholar 

  22. Cipolla BG, Havouis R, Moulinoux JP (2007) Polyamine contents in current foods: a basis for polyamine reduced diet and a study of its long term observance and tolerance in prostate carcinoma patients. Amino Acids 33:203–212. https://doi.org/10.1007/s00726-007-0524-1

    Article  CAS  Google Scholar 

  23. Thomas T, Thomas TJ (2003) Polyamine metabolism and cancer. J Cell Mol Med 7:113–126. https://doi.org/10.1111/j.1582-4934.2003.tb00210.x

    Article  CAS  Google Scholar 

  24. Alcázar R, Altabella T, Marco F et al (2010) Polyamines: molecules with regulatory functions in plant abiotic stress tolerance. Planta 231:1237–1249. https://doi.org/10.1007/s00425-010-1130-0

    Article  CAS  Google Scholar 

  25. Li Y, Sun H, Chen Z et al (2016) Implications of GABAergic neurotransmission in Alzheimer’s disease. Front Aging Neurosci 8:1–12. https://doi.org/10.3389/fnagi.2016.00031

    Google Scholar 

  26. Mody I, De Koninck Y, Otis TS, Soltesz I (1994) Bridging the cleft at GABA synapses in the brain. Trends Neurosci 17:517–525. https://doi.org/10.1016/0166-2236(94)90155-4

    Article  CAS  Google Scholar 

  27. Bouchereau A, Guénot P, Larher F (2000) Analysis of amines in plant materials. J Chromatogr B Biomed Sci Appl 747:49–67. https://doi.org/10.1016/S0378-4347(00)00286-3

    Article  CAS  Google Scholar 

  28. Minois N, Carmona-Gutierrez D, Madeo F (2011) Polyamines in aging and disease. Aging (Albany NY) 3:716–732. https://doi.org/10.1016/S0044-8486(03)00351-X

    Article  Google Scholar 

  29. Kusano T, Yamaguchi K, Berberich T, Takahashi Y (2007) Advances in polyamine research in 2007. J Plant Res 120:345–350. https://doi.org/10.1007/s10265-007-0074-3

    Article  CAS  Google Scholar 

  30. Lima GPP, Vianello F (2011) Review on the main differences between organic and conventional plant-based foods. Int J Food Sci Technol 46:1–13. https://doi.org/10.1111/j.1365-2621.2010.02436.x

    Article  CAS  Google Scholar 

  31. Wallace HM, Fraser AV (2004) Inhibitors of polyamine metabolism: review article. Amino Acids 26:353–365. https://doi.org/10.1007/s00726-004-0092-6

    Article  CAS  Google Scholar 

  32. Wallace H, Caslake R (2001) Polyamines and colon cancer. Eur J Gastroenterol Hepatol 13:1033. https://doi.org/10.1097/00042737-200109000-00006

    Article  CAS  Google Scholar 

  33. Narisawa T, Takahashi M, Niwa M et al (1989) Increased mucosal ornithine decarboxylase activity in large bowel with multiple tumors, adenocarcinoma, and adenoma. Cancer 63:1572–1576. https://doi.org/10.1002/1097-0142(19890415)63:8<1572::AID-CNCR2820630821>3.0.CO;2-U

    Article  CAS  Google Scholar 

  34. Gill SS, Tuteja N (2010) Polyamines and abiotic stress tolerance in plants. Plant Signal Behav 5:26–33. https://doi.org/10.4161/psb.5.1.10291

    Article  CAS  Google Scholar 

  35. Pottosin I, Shabala S (2014) Polyamines control of cation transport across plant membranes: implications for ion homeostasis and abiotic stress signaling. Front Plant Sci 5:1–16. https://doi.org/10.3389/fpls.2014.00154

    Article  Google Scholar 

  36. Edison TNJI, Atchudan R, Sethuraman MG, Lee YR (2016) Reductive-degradation of carcinogenic azo dyes using Anacardium occidentale testa derived silver nanoparticles. J Photochem Photobiol B Biol 162:604–610. https://doi.org/10.1016/j.jphotobiol.2016.07.040

    Article  CAS  Google Scholar 

  37. Rau DC, Parsegian VA (1992) Direct measurments of the intermolecular forces between counterion-condensed DNA double helices. Biophys J 61:246–259

    Article  CAS  Google Scholar 

  38. Schellman JA, Parthasarathy N (1984) X-ray diffraction studies on cation-collapsed DNA. J Mol Biol 175:313–329. https://doi.org/10.1016/0022-2836(84)90351-6

    Article  CAS  Google Scholar 

  39. Iacomino G, Picariello G, Stillitano I, D’Agostino L (2014) Nuclear aggregates of polyamines in a radiation-induced DNA damage model. Int J Biochem Cell Biol 47:11–19. https://doi.org/10.1016/j.biocel.2013.11.007

    Article  CAS  Google Scholar 

  40. Fujisawa S, Kadoma Y (2005) Kinetic evaluation of polyamines as radical scavengers. Anticancer Res 25:965–969

    CAS  Google Scholar 

  41. González-Montelongo R, Gloria Lobo M, González M (2010) Antioxidant activity in banana peel extracts: testing extraction conditions and related bioactive compounds. Food Chem 119:1030–1039. https://doi.org/10.1016/j.foodchem.2009.08.012

    Article  CAS  Google Scholar 

  42. Schneider Y, Vincent F, Duranton B et al (2000) Anti-proliferative effect of resveratrol, a natural component of grapes and wine, on human colonic cancer cells. Cancer Lett 158:85–91. https://doi.org/10.1016/S0304-3835(00)00511-5

    Article  CAS  Google Scholar 

  43. Moinard C, Cynober L, Debandt J (2005) Polyamines: metabolism and implications in human diseases. Clin Nutr 24:184–197. https://doi.org/10.1016/j.clnu.2004.11.001

    Article  CAS  Google Scholar 

  44. Cipolla B, Guillí F, Moulinoux J-P (2003) Polyamine-reduced diet in metastatic hormone-refractory prostate cancer (HRPC) patients. Biochem Soc Trans 31:384–387. https://doi.org/10.1042/BST0310384

    Article  CAS  Google Scholar 

  45. Murador DC, Mercadante AZ, De Rosso VV (2015) Cooking techniques improve the levels of bioactive compounds and antioxidant activity in kale and red cabbage. Food Chem 196:1101–1107. https://doi.org/10.1016/j.foodchem.2015.10.037

    Article  CAS  Google Scholar 

  46. Lima GPP, Costa SM, de Monaco KA et al (2017) Cooking processes increase bioactive compounds in organic and conventional green beans. Int J Food Sci Nutr 7486:1–12. https://doi.org/10.1080/09637486.2017.1324563

    Google Scholar 

  47. Drinkwater JM, Tsao R, Liu R et al (2015) Effects of cooking on rutin and glutathione concentrations and antioxidant activity of green asparagus (Asparagus officinalis) spears. J Funct Foods 12:342–353. https://doi.org/10.1016/j.jff.2014.11.013

    Article  CAS  Google Scholar 

  48. Gliszczyńska-Świgło A, Ciska E, Pawlak-Lemańska K et al (2006) Changes in the content of health-promoting compounds and antioxidant activity of broccoli after domestic processing. Food Addit Contam 23:1088–1098. https://doi.org/10.1080/02652030600887594

    Article  CAS  Google Scholar 

  49. Minatel IO, Borges CV, Ferreira MI et al (2017) Phenolic compounds: functional properties, impact of processing and bioavailability. Phenolic Compd-Biol Act. https://doi.org/10.5772/66368

  50. Bardocz S, Grant G, Brown DS et al (1993) Polyamines in food – implications for growth and health. J Nutr Biochem 4:66–71

    Article  CAS  Google Scholar 

  51. Kalač P (2014) Health effects and occurrence of dietary polyamines: a review for the period 2005–mid 2013. Food Chem 161:27–39. https://doi.org/10.1016/j.foodchem.2014.03.102

    Article  CAS  Google Scholar 

  52. Tassoni A, Tango N, Ferri M (2013) Comparison of biogenic amine and polyphenol profiles of grape berries and wines obtained following conventional, organic and biodynamic agricultural and oenological practices. Food Chem 139:405–413. https://doi.org/10.1016/j.foodchem.2013.01.041

    Article  CAS  Google Scholar 

  53. Leong SY, Oey I (2012) Effects of processing on anthocyanins, carotenoids and vitamin C in summer fruits and vegetables. Food Chem 133:1577–1587. https://doi.org/10.1016/j.foodchem.2012.02.052

    Article  CAS  Google Scholar 

  54. Gupta K, Sengupta A, Chakraborty M, Gupta B (2016) Hydrogen peroxide and polyamines act as double edged swords in plant abiotic stress responses. Front Plant Sci 7:1343. https://doi.org/10.3389/fpls.2016.01343

    Google Scholar 

  55. Faller ALK, Fialho E (2010) Polyphenol content and antioxidant capacity in organic and conventional plant foods. J Food Compos Anal 23:561–568. https://doi.org/10.1016/j.jfca.2010.01.003

    Article  CAS  Google Scholar 

  56. Lima GPP, da Rocha SA, Takaki M et al (2008) Comparison of polyamine, phenol and flavonoid contents in plants grown under conventional and organic methods. Int J Food Sci Technol 43:1838–1843. https://doi.org/10.1111/j.1365-2621.2008.01725.x

    Article  CAS  Google Scholar 

  57. Rossetto MRM, Vianello F, Saeki MJ, Lima GPP (2015) Polyamines in conventional and organic vegetables exposed to exogenous ethylene. Food Chem 188:218–224. https://doi.org/10.1016/j.foodchem.2015.04.125

    Article  CAS  Google Scholar 

  58. Winter CK, Davis SF (2006) Organic foods. J Food Sci 71:R117–R124. https://doi.org/10.1111/j.1750-3841.2006.00196.x

    Article  CAS  Google Scholar 

  59. Monaco KA, Costa SM, Minatel IO et al (2016) Influence of ozonated water sanitation on postharvest quality of conventionally and organically cultivated mangoes after postharvest storage. Postharvest Biol Technol 120:69–75. https://doi.org/10.1016/j.postharvbio.2016.05.003

    Article  CAS  Google Scholar 

  60. Cao YY, Chen YH, Chen MX et al (2016) Growth characteristics and endosperm structure of superior and inferior spikelets of indica rice under high-temperature stress. Biol Plant 60:532–542. https://doi.org/10.1007/s10535-016-0606-6

    Article  CAS  Google Scholar 

  61. da Silva Borges L, de Souza Vieira MC, Vianello F et al (2016) Antioxidant compounds of organically and conventionally fertilized jambu (Acmella oleracea). Biol Agric Hortic 32:149–158. https://doi.org/10.1080/01448765.2015.1103304

    Article  Google Scholar 

  62. Selmar D, Kleinwächter M (2013) Stress enhances the synthesis of secondary plant products: the impact of stress-related over-reduction on the accumulation of natural products. Plant Cell Physiol 54:817–826. https://doi.org/10.1093/pcp/pct054

    Article  CAS  Google Scholar 

  63. Kong J-Q (2015) Phenylalanine ammonia-lyase, a key component used for phenylpropanoids production by metabolic engineering. RSC Adv 5:62587–62603. https://doi.org/10.1039/C5RA08196C

    Article  CAS  Google Scholar 

  64. Oliveira AB, Moura CFH, Gomes-Filho E et al (2013) The impact of organic farming on quality of tomatoes is associated to increased oxidative stress during fruit development. PLoS One 8:e56354. https://doi.org/10.1371/journal.pone.0056354

    Article  CAS  Google Scholar 

  65. Vallverdú-Queralt A, Medina-Remón A, Casals-Ribes I, Lamuela-Raventos RM (2012) Is there any difference between the phenolic content of organic and conventional tomato juices? Food Chem 130:222–227. https://doi.org/10.1016/j.foodchem.2011.07.017

    Article  CAS  Google Scholar 

  66. Alasalvar C, Al-Farsi M, Quantick PC et al (2005) Effect of chill storage and modified atmosphere packaging (MAP) on antioxidant activity, anthocyanins, carotenoids, phenolics and sensory quality of ready-to-eat shredded orange and purple carrots. Food Chem 89:69–76. https://doi.org/10.1016/j.foodchem.2004.02.013

    Article  CAS  Google Scholar 

  67. McRae JM, Schulkin A, Kassara S et al (2013) Sensory properties of wine tannin fractions: implications for in-mouth sensory properties. J Agric Food Chem 61:719–727. https://doi.org/10.1021/jf304239n

    Article  CAS  Google Scholar 

  68. Corredor Z, Rodriguez-Ribera L, Coll E et al (2016) Unfermented grape juice reduce genomic damage on patients undergoing hemodialysis. Food Chem Toxicol 92:1–7. https://doi.org/10.1016/j.fct.2016.03.016

    Article  CAS  Google Scholar 

  69. Leong SY, Burritt DJ, Oey I (2016) Evaluation of the anthocyanin release and health-promoting properties of Pinot Noir grape juices after pulsed electric fields. Food Chem 196:833–841. https://doi.org/10.1016/j.foodchem.2015.10.025

    Article  CAS  Google Scholar 

  70. Vanzo A, Terdoslavich M, Brandoni A et al (2008) Uptake of grape anthocyanins into the rat kidney and the involvement of bilitranslocase. Mol Nutr Food Res 52:1106–1116. https://doi.org/10.1002/mnfr.200700505

    Article  CAS  Google Scholar 

  71. Bisht K, Wagner KH, Bulmer AC (2010) Curcumin, resveratrol and flavonoids as anti-inflammatory, cyto- and DNA-protective dietary compounds. Toxicology 278:88–100. https://doi.org/10.1016/j.tox.2009.11.008

    Article  CAS  Google Scholar 

  72. Mukhopadhyay P, Prajapati AK (2015) Quercetin in anti-diabetic research and strategies for improved quercetin bioavailability using polymer-based carriers – a review. RSC Adv 5:97547–97562. https://doi.org/10.1039/C5RA18896B

    Article  CAS  Google Scholar 

  73. Chen AY, Chen YC (2013) A review of the dietary flavonoid, kaempferol on human health and cancer chemoprevention. Food Chem 138:2099–2107. https://doi.org/10.1016/j.foodchem.2012.11.139

    Article  CAS  Google Scholar 

  74. Schlachterman A, Valle F, Wall KM et al (2008) Combined resveratrol, quercetin, and catechin treatment reduces breast tumor growth in a nude mouse model. Transl Oncol 1:19–27. https://doi.org/10.1593/tlo.07100

    Article  Google Scholar 

  75. Che J, Liang B, Zhang Y et al (2017) Kaempferol alleviates ox-LDL-induced apoptosis by up-regulation of autophagy via inhibiting PI3K/Akt/mTOR pathway in human endothelial cells. Cardiovasc Pathol 31:57. https://doi.org/10.1016/j.carpath.2017.08.001

    Article  CAS  Google Scholar 

  76. Choi JH, Park SE, Kim SJ, Kim S (2015) Kaempferol inhibits thrombosis and platelet activation. Biochimie 115:177–186. https://doi.org/10.1016/j.biochi.2015.06.001

    Article  CAS  Google Scholar 

  77. Nam S-Y, Jeong H-J, Kim H-M (2017) Kaempferol impedes IL-32-induced monocyte-macrophage differentiation. Chem Biol Interact 274:107–115. https://doi.org/10.1016/j.cbi.2017.07.010

    Article  CAS  Google Scholar 

  78. Iacopini P, Baldi M, Storchi P, Sebastiani L (2008) Catechin, epicatechin, quercetin, rutin and resveratrol in red grape: content, in vitro antioxidant activity and interactions. J Food Compos Anal 21:589–598. https://doi.org/10.1016/j.jfca.2008.03.011

    Article  CAS  Google Scholar 

  79. Grujic-Milanovic J, Miloradovic Z, Jovovic D et al (2017) The red wine polyphenol, resveratrol improves hemodynamics, oxidative defence and aortal structure in essential and malignant hypertension. J Funct Foods 34:266–276. https://doi.org/10.1016/j.jff.2017.04.035

    Article  CAS  Google Scholar 

  80. Oh M, Lee JH, Bae SY et al (2015) Protective effects of red wine and resveratrol for foodborne virus surrogates. Food Control 47:502–509. https://doi.org/10.1016/j.foodcont.2014.07.056

    Article  CAS  Google Scholar 

  81. Norouzzadeh M, Amiri F, Saboor-Yaraghi AA et al (2017) Does resveratrol improve insulin signalling in HepG2 cells? Can J Diabetes 41:211–216. https://doi.org/10.1016/j.jcjd.2016.09.015

    Article  Google Scholar 

  82. Fernandes I, Faria A, Calhau C et al (2014) Bioavailability of anthocyanins and derivatives. J Funct Foods 7:54–66. https://doi.org/10.1016/j.jff.2013.05.010

    Article  CAS  Google Scholar 

  83. Fu Y, Zhou E, Wei Z et al (2014) Cyanidin-3-O-β-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts. Biochem Pharmacol 90:126–134. https://doi.org/10.1016/j.bcp.2014.05.004

    Article  CAS  Google Scholar 

  84. Fratantonio D, Cimino F, Molonia MS et al (2017) Cyanidin-3-O-glucoside ameliorates palmitate-induced insulin resistance by modulating IRS-1 phosphorylation and release of endothelial derived vasoactive factors. Biochim Biophys Acta Mol Cell Biol Lipids 1862:351–357. https://doi.org/10.1016/j.bbalip.2016.12.008

    Article  CAS  Google Scholar 

  85. Ferrari D, Speciale A, Cristani M et al (2016) Cyanidin-3-O-glucoside inhibits NF-kB signalling in intestinal epithelial cells exposed to TNF-α and exerts protective effects via Nrf2 pathway activation. Toxicol Lett 264:51–58. https://doi.org/10.1016/j.toxlet.2016.10.014

    Article  CAS  Google Scholar 

  86. Chen P-N, Chu S-C, Chiou H-L et al (2006) Mulberry anthocyanins, cyanidin 3-rutinoside and cyanidin 3-glucoside, exhibited an inhibitory effect on the migration and invasion of a human lung cancer cell line. Cancer Lett 235:248–259. https://doi.org/10.1016/j.canlet.2005.04.033

    Article  CAS  Google Scholar 

  87. Decendit A, Mamani-Matsuda M, Aumont V et al (2013) Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats. Biochem Pharmacol 86:1461–1467. https://doi.org/10.1016/j.bcp.2013.06.010

    Article  CAS  Google Scholar 

  88. Mackert JD, McIntosh MK (2016) Combination of the anthocyanidins malvidin and peonidin attenuates lipopolysaccharide-mediated inflammatory gene expression in primary human adipocytes. Nutr Res 36:1353–1360. https://doi.org/10.1016/j.nutres.2016.11.003

    Article  CAS  Google Scholar 

  89. Khandelwal N, Abraham SK (2014) Intake of anthocyanidins pelargonidin and cyanidin reduces genotoxic stress in mice induced by diepoxybutane, urethane and endogenous nitrosation. Environ Toxicol Pharmacol 37:837–843. https://doi.org/10.1016/j.etap.2014.02.012

    Article  CAS  Google Scholar 

  90. Sohanaki H, Baluchnejadmojarad T, Nikbakht F, Roghani M (2016) Pelargonidin improves memory deficit in amyloid β25-35 rat model of Alzheimer’s disease by inhibition of glial activation, cholinesterase, and oxidative stress. Biomed Pharmacother 83:85–91. https://doi.org/10.1016/j.biopha.2016.06.021

    Article  CAS  Google Scholar 

  91. Son JE, Jeong H, Kim H et al (2014) Pelargonidin attenuates PDGF-BB-induced aortic smooth muscle cell proliferation and migration by direct inhibition of focal adhesion kinase. Biochem Pharmacol 89:236–245. https://doi.org/10.1016/j.bcp.2014.02.015

    Article  CAS  Google Scholar 

  92. Lim W, Jeong W, Song G (2016) Delphinidin suppresses proliferation and migration of human ovarian clear cell carcinoma cells through blocking AKT and ERK1/2 MAPK signaling pathways. Mol Cell Endocrinol 422:172–181. https://doi.org/10.1016/j.mce.2015.12.013

    Article  CAS  Google Scholar 

  93. Sobiepanek A, Milner-Krawczyk M, Bobecka-Wesołowska K, Kobiela T (2016) The effect of delphinidin on the mechanical properties of keratinocytes exposed to UVB radiation. J Photochem Photobiol B Biol 164:264–270. https://doi.org/10.1016/j.jphotobiol.2016.09.038

    Article  CAS  Google Scholar 

  94. Zang LY, Cosma G, Gardner H et al (2000) Effect of antioxidant protection by p-coumaric acid on low-density lipoprotein cholesterol oxidation. Am J Phys Cell Phys 279:C954–C960

    Article  CAS  Google Scholar 

  95. Bami E, Ozakpınar OB, Ozdemir-Kumral ZN et al (2017) Protective effect of ferulic acid on cisplatin induced nephrotoxicity in rats. Environ Toxicol Pharmacol 54:105–111. https://doi.org/10.1016/j.etap.2017.06.026

    Article  CAS  Google Scholar 

  96. Miao M, Cao L, Li R et al (2017) Protective effect of chlorogenic acid on the focal cerebral ischemia reperfusion rat models. Saudi Pharm J 25:556–563. https://doi.org/10.1016/j.jsps.2017.04.023

    Article  Google Scholar 

  97. Meng S, Cao J, Feng Q et al (2013) Roles of chlorogenic acid on regulating glucose and lipids metabolism: a review. Evid-Based Complement Alternat Med 2013:1–11. https://doi.org/10.1155/2013/801457

    Google Scholar 

  98. Huang Y, Chen H, Zhou X et al (2017) Inhibition effects of chlorogenic acid on benign prostatic hyperplasia in mice. Eur J Pharmacol 809:191–195. https://doi.org/10.1016/j.ejphar.2017.04.017

    Article  CAS  Google Scholar 

  99. Martin-Tanguy J (1985) The occurrence and possible function of hydroxycinnamoyl acid amides in plants. Plant Growth Regul 3:381–399. https://doi.org/10.1007/BF00117595

    Article  CAS  Google Scholar 

  100. Bassard JE, Ullmann P, Bernier F, Werck-Reichhart D (2010) Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 71:1808–1824. https://doi.org/10.1016/j.phytochem.2010.08.003

    Article  CAS  Google Scholar 

  101. Blagbrough IS, Moya E, Taylor S (1994) Polyamines and polyamine amides from wasps and spiders. Biochem Soc Trans 22:888–893

    Article  CAS  Google Scholar 

  102. Walters D, Cowley T, Mitchell A (2002) Methyl jasmonate alters polyamine metabolism and induces systemic protection against powdery mildew infection in barley seedlings. J Exp Bot 53:747–756. https://doi.org/10.1093/jexbot/53.369.747

    Article  CAS  Google Scholar 

  103. Edreva AM, Velikova VB, Tsonev TD (2007) Phenylamides in plants. Russ J Plant Physiol 54:287–301. https://doi.org/10.1134/S1021443707030016

    Article  CAS  Google Scholar 

  104. Yonei S, Furui H (1981) Lethal and mutagenic effects of malondialdehyde, a decomposition product of peroxidized lipids, on Escherichia coli with different DNA-repair capacities. Mutat Res 88:23–32

    Article  CAS  Google Scholar 

  105. Pariza MW (1982) Mutagens in heated foods. Food Technol 36:53

    CAS  Google Scholar 

  106. Nakatani N, Inatani R, Ohta H, Nishioka A (1986) Chemical constituents of peppers (Piper spp.) and application to food preservation: naturally occurring antioxidative compounds. Environ Health Perspect 67:135–142. https://doi.org/10.1289/ehp.8667135

    Article  CAS  Google Scholar 

  107. Kusano T, Berberich T, Tateda C, Takahashi Y (2008) Polyamines: essential factors for growth and survival. Planta 228:367–381. https://doi.org/10.1007/s00425-008-0772-7

    Article  CAS  Google Scholar 

  108. Melgarejo E, Urdiales JL, Sánchez-Jiménez F, Medina MÁ (2010) Targeting polyamines and biogenic amines by green tea epigallocatechin-3-gallate. Amino Acids 38:519–523. https://doi.org/10.1007/s00726-009-0411-z

    Article  CAS  Google Scholar 

  109. Pegg AE (1988) Polyamine metabolism and its importance in neoplastic growth and as a target for chemotherapy. Cancer Res 48:759–774

    CAS  Google Scholar 

  110. Wolter F, Ulrich S, Stein J (2004) Molecular mechanisms of the chemopreventive effects of resveratrol and its abalogs in colorectal cancer. Key role of polyamines. J Nutr 134:3219–3222

    CAS  Google Scholar 

  111. Bertoldi M, Gonsalvi M, Borri Voltattorni C (2001) Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase. Biochem Biophys Res Commun 284:90–93. https://doi.org/10.1006/bbrc.2001.4945

    Article  CAS  Google Scholar 

  112. Yamashita K, Suzuki Y, Matsui T et al (2000) Epigallocatechin gallate inhibits histamine release from rat basophilic leukemia (RBL-2H3) cells: role of tyrosine phosphorylation pathway. Biochem Biophys Res Commun 274:603–608. https://doi.org/10.1006/bbrc.2000.3200

    Article  CAS  Google Scholar 

  113. Rodríguez-Caso C, Rodríguez-Agudo D, Sánchez-Jiménez F, Medina MA (2003) Green tea epigallocatechin-3-gallate is an inhibitor of mammalian histidine decarboxylase. Cell Mol Life Sci 60:1760–1763. https://doi.org/10.1007/s00018-003-3135-3

    Article  CAS  Google Scholar 

  114. Alberto MR, Arena ME, Manca de Nadra MC (2007) Putrescine production from agmatine by Lactobacillus hilgardii: effect of phenolic compounds. Food Control 18:898–903. https://doi.org/10.1016/j.foodcont.2006.05.006

    Article  CAS  Google Scholar 

  115. Cardona F, Andrés-Lacueva C, Tulipani S et al (2013) Benefits of polyphenols on gut microbiota and implications in human health. J Nutr Biochem 24:1415–1422. https://doi.org/10.1016/j.jnutbio.2013.05.001

    Article  CAS  Google Scholar 

  116. Kutschera M, Engst W, Blaut M, Braune A (2011) Isolation of catechin-converting human intestinal bacteria. J Appl Microbiol 111:165–175. https://doi.org/10.1111/j.1365-2672.2011.05025.x

    Article  CAS  Google Scholar 

  117. Bandele OJ, Clawson SJ, Osheroff N (2008) Dietary polyphenols as topoisomerase II poisons: B ring and C ring substituents determine the mechanism of enzyme-mediated DNA cleavage enhancement. Chem Res Toxicol 21:1253–1260. https://doi.org/10.1021/tx8000785

    Article  CAS  Google Scholar 

  118. Pommier Y, Leo E, Zhang H, Marchand C (2010) DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem Biol 17:421–433. https://doi.org/10.1016/j.chembiol.2010.04.012

    Article  CAS  Google Scholar 

  119. Pastoriza S, Mesías M, Cabrera C, Rufián-Henares JA (2017) Healthy properties of green and white teas: an update. Food Funct 8:2650–2662. https://doi.org/10.1039/c7fo00611j

    Article  CAS  Google Scholar 

  120. Opitz SEW, Goodman BA, Keller M et al (2017) Understanding the effects of roasting on antioxidant components of coffee brews by coupling on-line ABTS assay to high performance size exclusion chromatography. Phytochem Anal 28:106–114. https://doi.org/10.1002/pca.2661

    Article  CAS  Google Scholar 

  121. Rivero D, Pérez-Magariño S, González-Sanjosé ML et al (2005) Inhibition of induced DNA oxidative damage by beers: correlation with the content of polyphenols and Melanoidins. J Agric Food Chem 53:3637–3642. https://doi.org/10.1021/jf048146v

    Article  CAS  Google Scholar 

  122. Crozier TWM, Stalmach A, Lean MEJ, Crozier A (2012) Espresso coffees, caffeine and chlorogenic acid intake: potential health implications. Food Funct 3:30–33. https://doi.org/10.1039/C1FO10240K

    Article  CAS  Google Scholar 

  123. Murase T, Yokoi Y, Misawa K et al (2012) Coffee polyphenols modulate whole-body substrate oxidation and suppress postprandial hyperglycaemia, hyperinsulinaemia and hyperlipidaemia. Br J Nutr 107:1757–1765. https://doi.org/10.1017/S0007114511005083

    Article  CAS  Google Scholar 

  124. Natella F, Nardini M, Giannetti I et al (2002) Coffee drinking influences plasma antioxidant capacity in humans. J Agric Food Chem 50:6211–6216. https://doi.org/10.1021/jf025768c

    Article  CAS  Google Scholar 

  125. Hoelzl C, Knasmüller S, Wagner K-H et al (2010) Instant coffee with high chlorogenic acid levels protects humans against oxidative damage of macromolecules. Mol Nutr Food Res 54:1722–1733. https://doi.org/10.1002/mnfr.201000048

    Article  CAS  Google Scholar 

  126. Lecumberri E, Dupertuis YM, Miralbell R, Pichard C (2013) Green tea polyphenol epigallocatechin-3-gallate (EGCG) as adjuvant in cancer therapy. Clin Nutr 32:894–903. https://doi.org/10.1016/j.clnu.2013.03.008

    Article  CAS  Google Scholar 

  127. Fantini M, Benvenuto M, Masuelli L et al (2015) In vitro and in vivo antitumoral effects of combinations of polyphenols, or polyphenols and anticancer drugs: perspectives on cancer treatment. Int J Mol Sci 16:9236–9282. https://doi.org/10.3390/ijms16059236

    Article  CAS  Google Scholar 

  128. Ho JWS, Cheung MWM (2014) Combination of phytochemicals as adjuvants for cancer therapy. Recent Pat Anticancer Drug Discov 9:297–302

    Article  CAS  Google Scholar 

  129. Okarter N, Liu RH (2010) Health benefits of whole grain phytochemicals. Crit Rev Food Sci Nutr 50:193–208. https://doi.org/10.1080/10408390802248734

    Article  CAS  Google Scholar 

  130. Zhang Y-J, Gan R-Y, Li S et al (2015) Antioxidant phytochemicals for the prevention and treatment of chronic diseases. Molecules 20:21138–21156. https://doi.org/10.3390/molecules201219753

    Article  CAS  Google Scholar 

  131. Kaulmann A, Bohn T (2014) Carotenoids, inflammation, and oxidative stress – implications of cellular signaling pathways and relation to chronic disease prevention. Nutr Res 34:907–929. https://doi.org/10.1016/j.nutres.2014.07.010

    Article  CAS  Google Scholar 

  132. Minatel IO, Francisqueti FV, Corrêa CR, Lima GPP (2016) Antioxidant activity of γ-Oryzanol: a complex network of interactions. Int J Mol Sci 17:1107. https://doi.org/10.3390/ijms17081107

    Article  CAS  Google Scholar 

  133. Carnésecchi S, Schneider Y, Lazarus SA et al (2002) Flavanols and procyanidins of cocoa and chocolate inhibit growth and polyamine biosynthesis of human colonic cancer cells. Cancer Lett 175:147–155. https://doi.org/10.1016/S0304-3835(01)00731-5

    Article  Google Scholar 

  134. Zhang M, Wang H, Tracey KJ (2000) Regulation of macrophage activation and inflammation by spermine: a new chapter in an old story. Crit Care Med 28:N60–N66

    Article  CAS  Google Scholar 

  135. Adibhatla RM, Hatcher JF, Sailor K, Dempsey RJ (2002) Polyamines and central nervous system injury: spermine and spermidine decrease following transient focal cerebral ischemia in spontaneously hypertensive rats. Brain Res 938:81–86. https://doi.org/10.1016/S0006-8993(02)02447-2

    Article  CAS  Google Scholar 

  136. Lee S-Y, Kim C-Y, Lee J-J et al (2003) Effects of delayed administration of (−)-epigallocatechin gallate, a green tea polyphenol on the changes in polyamine levels and neuronal damage after transient forebrain ischemia in gerbils. Brain Res Bull 61:399–406. https://doi.org/10.1016/S0361-9230(03)00139-4

    Article  CAS  Google Scholar 

  137. Brooks WH (2013) Increased polyamines alter chromatin and stabilize autoantigens in autoimmune diseases. Front Immunol 4:91. https://doi.org/10.3389/fimmu.2013.00091

    Article  CAS  Google Scholar 

  138. Hanfrey CC, Pearson BM, Hazeldine S et al (2011) Alternative spermidine biosynthetic route is critical for growth of campylobacter jejuni and is the dominant polyamine pathway in human gut microbiota. J Biol Chem 286:43301–43312. https://doi.org/10.1074/jbc.M111.307835

    Article  CAS  Google Scholar 

  139. Di Martino ML, Campilongo R, Casalino M et al (2013) Polyamines: emerging players in bacteria–host interactions. Int J Med Microbiol 303:484–491. https://doi.org/10.1016/j.ijmm.2013.06.008

    Article  CAS  Google Scholar 

  140. Tabor H, Tabor CW, Rosenthal SM (1961) The biochemistry of the polyamines: spermidine and spermine. Annu Rev Biochem 30:579–604. https://doi.org/10.1146/annurev.bi.30.070161.003051

    Article  CAS  Google Scholar 

  141. Mullen W, Archeveque M-A, Edwards CA et al (2008) Bioavailability and metabolism of orange juice flavanones in humans: impact of a full-fat yogurt. J Agric Food Chem 56:11157–11164. https://doi.org/10.1021/jf801974v

    Article  CAS  Google Scholar 

  142. Yamamoto M, Jokura H, Hashizume K et al (2013) Hesperidin metabolite hesperetin-7-O-glucuronide, but not hesperetin-3′-O-glucuronide, exerts hypotensive, vasodilatory, and anti-inflammatory activities. Food Funct 4:1346. https://doi.org/10.1039/c3fo60030k

    Article  CAS  Google Scholar 

  143. Lentini A, Forni C, Provenzano B, Beninati S (2007) Enhancement of transglutaminase activity and polyamine depletion in B16-F10 melanoma cells by flavonoids naringenin and hesperitin correlate to reduction of the in vivo metastatic potential. Amino Acids 32:95–100. https://doi.org/10.1007/s00726-006-0304-3

    Article  CAS  Google Scholar 

  144. Young JE, Zhao X, Carey EE et al (2005) Phytochemical phenolics in organically grown vegetables. Mol Nutr Food Res 49:1136–1142. https://doi.org/10.1002/mnfr.200500080

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors are grateful to the National Council for Scientific and Technological Development (CNPq, Brazil) (305177/2015-0), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (02441/09-8) and the São Paulo Research Foundation (FAPESP) (2016/22665-2)

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Giuseppina Pace Pereira Lima .

Editor information

Editors and Affiliations

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

Gomez-Gomez, H.A., Borges, C.V., Minatel, I.O., Luvizon, A.C., Lima, G.P.P. (2018). Health Benefits of Dietary Phenolic Compounds and Biogenic Amines. 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_27-2

Download citation

  • DOI: https://doi.org/10.1007/978-3-319-54528-8_27-2

  • 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

Chapter history

  1. Latest

    Health Benefits of Dietary Phenolic Compounds and Biogenic Amines
    Published:
    12 January 2018

    DOI: https://doi.org/10.1007/978-3-319-54528-8_27-2

  2. Original

    Heath Benefits of Dietary Phenolic Compounds and Biogenic Amines
    Published:
    22 November 2017

    DOI: https://doi.org/10.1007/978-3-319-54528-8_27-1