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Proanthocyanidins of Cocoa: Bioavailability and Biological Activities

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Natural Products

Abstract

Cocoa and dark chocolate contain many active compounds, which seem to play some pharmacological roles both in vitro and in human. Many studies have focused their attention on polyphenol content, which is elevated in cocoa beans and in some kind of dark chocolate, depending on harvest and postharvest handling. Procyanidins monomers and oligomers modulate a large quantity of biological mechanisms. Indeed, scientists might be more interested to better understand pharmacological aspects of such compounds in vivo and their mechanisms of action and interactions with other molecules as well as new medicines. Moreover, some potential adverse effects have to be taken into prompt consideration. This chapter, which is not the result of a specific experimental work but only a short study of recent bibliography on the specific subject, might help in understanding some aspects connected with the chemistry of cocoa and chocolate.

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Abbreviations

APP:

Amyloid precursor protein

Aß:

Amyloid beta

AUC:

Area under the curve

BBB:

Blood-brain barrier

COX-2:

Cyclooxygenase 2

EDR:

Endothelium-dependent relaxation

EGCG:

Epigallocatechin gallate

HDL-c:

High-density lipoprotein cholesterol

iNOS:

Nitric oxide synthases

LDL-c:

Low-density lipoprotein cholesterol

mDP:

Mean degree of polymerization

NFCS:

Nonfat cocoa solids

NF-kB:

Nuclear factor kappa-light-chain-enhancer of activated B cells

NO:

Nitric oxide

NOAEL:

No observed adverse effect level

ORAC:

Oxygen radical absorbance capacity

pKa:

Acidity constant

UGT:

Uridine 5′-diphospho-glucuronosyltransferase

References

  1. Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ (2003) Am J Clin Nutr 77:1466

    CAS  Google Scholar 

  2. Foo LY, Lu Y, Howell AB, Vorsa N (2000) J Nat Prod 63:1225

    Article  CAS  Google Scholar 

  3. Williamson G, Manach C (2005) Am J Clin Nutr 81:243S

    CAS  Google Scholar 

  4. Engler MB, Engler MM (2006) Nutr Rev 64:109

    Article  Google Scholar 

  5. Ding EL, Hutfless SM, Ding X, Girotra S (2006) Nutr Metab (Lond) 3:1

    Article  CAS  Google Scholar 

  6. Corti R, Flammer AJ, Hollenberg NK, Lüscher TF (2009) Circulation 119:1433

    Article  Google Scholar 

  7. Santos-Buelga C, Scalbert A (2000) J Sci Food Agric 80:1094

    Article  CAS  Google Scholar 

  8. Espin CI, Garcia-Conesa MT, Tomas-Barberan FA (2007) Phytochemistry 68:2986

    Article  CAS  Google Scholar 

  9. Lee KW, Kim YJ, Lee HJ, Lee CY (2003) J Agric Food Chem 51:7292

    Article  CAS  Google Scholar 

  10. USDA National Nutrient Database for Standard Reference (2011) Release 24

    Google Scholar 

  11. Perez-Jimenez J, Neveu V, Vos F, Scalbert A (2010) Eur J Clin Nutr 64:S112

    Article  CAS  Google Scholar 

  12. USDA Database for the Proanthocyanidin Content of Selected Foods (2004) Aug

    Google Scholar 

  13. Kühnau J (1976) World Rev Nutr Diet 24:117

    Google Scholar 

  14. Ovaskainen ML, Torronen R, Koponen JM, Sinkko H, Helistrom J, Reinivuo H (2008) J Nutr 138:562

    CAS  Google Scholar 

  15. Bravo L (1998) Nutr Rev 56:317

    Article  CAS  Google Scholar 

  16. Robbins RL, Kwik-Uribe C, Hammerstone JF, Schmitz HH (2006) J Cardiovasc Pharmacol 47:S110

    Article  CAS  Google Scholar 

  17. Pinorini MT, Colombo ML, Conti A (2011) In: Paoletti R, Poli A, Visioli A, Conti A (eds) Chocolate and health. Springer, Milano

    Google Scholar 

  18. Borchers AT, Keen CL, Hannum SM, Gerschwin ME (2000) J Medic Food 3:77

    Article  CAS  Google Scholar 

  19. Counet C, Ouwerx C, Rosoux D, Collin S (2004) J Agric Food Chem 52:6243

    Article  CAS  Google Scholar 

  20. Miller KB, Stuart DA, Smith NL, Lee CY, McHale NL, Flanagan JA, Ou B, Hurst J (2006) J Agric Food Chem 54:4062

    Article  CAS  Google Scholar 

  21. Kelm MA, Johnson JC, Robbins RJ, Hammerstone JF, Schmitz HH (2006) J Agric Food Chem 54:1571

    Article  CAS  Google Scholar 

  22. Clapperton J, Lockwood R, Romanczyk L, Hammerstone JF (1994) Trop Agric 71:303

    Google Scholar 

  23. Clapperton J, Hammerstone JF, Romanczyk R, Yow S, Chan J, Lin D, Lockwood R (1992) In: Proceedings of the 16th international conference of groupe polyphenols, Lisbon

    Google Scholar 

  24. Cooper KA, Donovan JL, Waterhouse AL, Williamson G (2008) Br J Nutr 99:1

    Article  CAS  Google Scholar 

  25. Rusconi M, Conti A (2010) Pharm Res 61:5

    Article  CAS  Google Scholar 

  26. Ultee AJ, van Dorsen J (1909) In: JaVa agriculture station report 33

    Google Scholar 

  27. Adam WB, Hardy P, Nierenstein M (1931) J Am Chem Soc 53:727

    Article  CAS  Google Scholar 

  28. Freudenberg K, Cox RFB, Braun E (1932) J Am Chem Soc 54:1913

    Article  CAS  Google Scholar 

  29. Knapp AW, Hearne JF (1939) Analyst 64:475

    Article  CAS  Google Scholar 

  30. Forsyth WGC (1955) Biochem J 60:108

    CAS  Google Scholar 

  31. Hammerstone JF, Lazarus SA, Mitchell AE, Rucker R, Schmitz HH (1999) J Agric Food Chem 47:490

    Article  CAS  Google Scholar 

  32. Adamson GE, Lazarus SA, Mitchell AE, Prior RL, Cao G, Jacobs PH, Kremers BG, Hammerstone JF, Rucker RB, Ritter KA, Schmitz HH (1999) J Agric Food Chem 47:4184

    Article  CAS  Google Scholar 

  33. Schramm DD, Wang JF, Holt RR, Ensunsa JL, Gonsalves JL, Lazarus SA, Schmitz HH, German JB, Keen CL (2001) Am J Clin Nutr 73:36–40

    CAS  Google Scholar 

  34. Wang JF, Schramm DD, Holt RR, Ensunsa JL, Fraga CG, Schmitz HH, Keen CL (2000) J Nutr 130:2115S

    CAS  Google Scholar 

  35. Karim M, McCormick K, Kappagoda CT (2000) J Nutr 130:2105S

    CAS  Google Scholar 

  36. Holt RR, Lazarus SA, Sullard MC, Zhu QY, Schramm DD, Hammerstone JF, Fraga CG, Schmitz HH, Keen CL (2002) Am J Clin Nutr 76:798

    CAS  Google Scholar 

  37. Fraga CG (2007) IUBMB Life 59:308

    Article  CAS  Google Scholar 

  38. Galleano M, Oteiza PI, Fraga CG (2009) J Cardiovasc Pharmacol 54:483

    Article  CAS  Google Scholar 

  39. Gu L, House SE, Wu X et al (2006) J Agric Food Chem 54:4057

    Google Scholar 

  40. Wollgast J, Anklam A (2000) Food Res Int 33:423

    Article  CAS  Google Scholar 

  41. Arts ICW, Van de Putte B, Hollman CH (2000) J Agric Food Chem 48:1746

    Article  CAS  Google Scholar 

  42. Manach C, Scalbert A, Morand C et al (2004) Am J Clin Nutr 79:727

    CAS  Google Scholar 

  43. Lamuela-Raventos RM, Romero-Perez AI, Andres-Lacueva C, Tornero A (2005) Food Sci Technol Int 11:159

    Article  CAS  Google Scholar 

  44. Cooper KA, Campos-Gimenez E, Alvarez DJ, Nagy K, Donovan JL, Williamson G (2007) J Agric Food Chem 55:2841

    Article  CAS  Google Scholar 

  45. Miller KB, Hurst WJ, Flannigan N, Ou B, Lee CY, Smith N, Stuart DA (2009) J Agric Food Chem 57:9169

    Article  CAS  Google Scholar 

  46. Mathur S, Devaraj S, Grundy SM, Jialal I (2002) J Nutr 132:3663

    CAS  Google Scholar 

  47. Mursu J, Voutilainen S, Nurmi T, Rissanez TH, Virtanen JK, Kaikkonen J, Nyyssonen K, Salonen JT (2004) Free Radic Biol Med 37:1351

    Article  CAS  Google Scholar 

  48. Wan Y, Vinson JA, Etherton TD, Proch J, Lazarus SA, Kris-Etherton PM (2001) Am J Clin Nutr 74:596

    CAS  Google Scholar 

  49. Kris-Etherton PM, Derr JA, Mustad VA, Seligson FH, Pearson TA (1994) Am J Clin Nutr 60:1037S

    CAS  Google Scholar 

  50. Amin I, Koh BK, Asmah R (2004) J Med Food 7:7

    Article  CAS  Google Scholar 

  51. Bisson JF, Guardia-Llorens MA, Hidalgo S, Rozan P, Messaoudi M (2008) Eur J Can Prev 17:54

    Article  Google Scholar 

  52. Bisson JF, Hidalgo S, Rozan P, Messaoudi M (2007) J Med Food 10:628

    Article  CAS  Google Scholar 

  53. Bisson JF, Nejdi A, Rozan P, Hidalgo S, Lalonde R, Messaoudi M (2008) Br J Nutr 100:94

    Article  CAS  Google Scholar 

  54. Rozan P, Hidalgo S, Nejdi A, Bisson JF, Lalonde R, Messaoudi M (2006) J Food Sci 72:S203

    Article  CAS  Google Scholar 

  55. Jalil AMM, Ismail A (2008) Molecules 13:2190

    Article  CAS  Google Scholar 

  56. Levites Y, Amit T, Youdim MB, Mandel S (2002) J Biol Chem 277:30574

    Article  CAS  Google Scholar 

  57. Singh M, Arseneault M, Sanderson T, Murthy V, Ramassamy C (2008) J Agric Food Chem 56:4855

    Article  CAS  Google Scholar 

  58. Levites Y, Amit T, Mandel S, Youdim MB (2003) FASEB J 17:952

    CAS  Google Scholar 

  59. Suganuma M, Okabe S, Oniyama M, Tada Y, Ito H, Fujiki H (1998) Carcinogenesis 19:1771

    Article  CAS  Google Scholar 

  60. Skrzydlewska E, Augustyniak A, Michalak K, Farbiszewski R (2005) Alcohol 37:89

    Article  CAS  Google Scholar 

  61. Erba D, Riso P, Criscuoli F, Testolin G (2003) Nutrition 19:545

    Article  CAS  Google Scholar 

  62. Bickford PC, Gould T, Briederick L, Chadman K, Pollock A, Young D, Shukitt-Hale B, Joseph J (2000) Brain Res 866:211

    Article  CAS  Google Scholar 

  63. Guo S, Bezard E, Zhao B (2005) Free Radic Biol Med 39:682

    Article  CAS  Google Scholar 

  64. Elbling L, Weiss RM, Teufelhofer O, Uhl M, Knasmueller S, Schulte-Hermann R, Berger W, Micksche M (2005) FASEB J 19:807

    CAS  Google Scholar 

  65. Furukawa A, Oikawa S, Murata M, Hiraku Y, Kawanishi S (2003) Biochem Pharmacol 66:1769

    Article  CAS  Google Scholar 

  66. Oikawa S, Furukawaa A, Asada H, Hirakawa K, Kawanishi S (2003) Free Radical Res 37:881

    Article  CAS  Google Scholar 

  67. Levites Y, Youdim MB, Maor G, Mandel S (2002) Biochem Pharmacol 63:21

    Article  CAS  Google Scholar 

  68. Weinreb O, Mandel S, Amit T, Youdim MB (2004) J Nutr Biochem 15:506

    Article  CAS  Google Scholar 

  69. Manach C, Williamson G, Morand C, Scalbert A, Rémésy C (2005) Am J Clin Nutr 81:230S

    CAS  Google Scholar 

  70. Rimbach G, Melchin M, Moehring J, Wagner A (2009) Int J Mol Sci 10:4290

    Article  CAS  Google Scholar 

  71. Scalbert A, Williamson G (2000) J Nutr 130:2073S

    CAS  Google Scholar 

  72. Higuchi WI, Ho NF, Park JY, Komiya I (1981) Rate-limiting steps and factors in drug absorption. In: Prescott LF, Nimno WS (eds) Drug absorption. ADIS Press, New York, p 35

    Google Scholar 

  73. Ho NF, Park JY, Ni PF, Higuchi WI (1983) Advancing quantitative and mechanistic approaches in interfacing gastrointestinal drug absorption studies in animal and humans. In: Crouthamel W, Sarapu AC (eds) Animal models for oral drug delivery. In situ and in vivo approaches. American Pharmaceutical Association, Washington, DC, p 27

    Google Scholar 

  74. Scalbert A (1991) Phytochemistry 30:3875

    Article  CAS  Google Scholar 

  75. Jimenez-Ramsey LM, Rogler JC, Housley TL, Butler L, Elkin RG (1994) J Agric Food Chem 42:963

    Article  CAS  Google Scholar 

  76. Gonthier M, Donovan J, Texier O, Felgines C, Remesy C, Scalbert A (2003) Free Radic Biol Med 35:837

    Article  CAS  Google Scholar 

  77. Tomas-Barberan F, Cienfuegos-Jovellanos E, Marin A, Muguerza B, Gil-Izquierdo A, Cerda B (2007) J Agric Food Chem 55:3926

    Article  CAS  Google Scholar 

  78. Youdim KA, Dobbie MS, Kuhnle G, Proteggente AR, Abbott NJ, Rice-Evans C (2003) J Neurochem 85:180

    Article  CAS  Google Scholar 

  79. Youdim KA, Shukitt-Hale B, Joseph JA (2004) Free Radic Biol Med 37:1683

    Article  CAS  Google Scholar 

  80. Kroemer HK, Klotz U (1992) Clin Pharmacokinet 23:292

    Article  CAS  Google Scholar 

  81. Spencer JPE, Choudry F, Pannala AS, Srai SK, Debnam ES, Rice Evans C (2000) Biochem Biophys Res Commun 272:236

    Article  CAS  Google Scholar 

  82. Yoshino K, Suzuki M, Sasaki K, Miyase T, Sano M (1999) J Nutr Biochem 10:223

    Article  CAS  Google Scholar 

  83. Serafini M, Bugianesi R, Maiani G, Valtuena S, De Santis S, Crozier A (2003) Nature 424:1013

    Article  CAS  Google Scholar 

  84. Mullen W, Borges G, Donovan JL, Edwards CA, Serafini M, Lean ME, Crozier A (2009) Am J Clin Nutr 89:1784

    Article  CAS  Google Scholar 

  85. Ortega N, Reguant J, Romero MP, Macià A, Motilva MJ (2009) J Agric Food Chem 57:5743

    Article  CAS  Google Scholar 

  86. Neilson AP, Sapper TN, Janle EM, Rudolph R, Matusheski NV, Ferruzzi MG (2010) J Agric Food Chem 58:6685

    Article  CAS  Google Scholar 

  87. Donovan JL, Crespy V, Oliveira M, Cooper KA, Gibson BB, Williamson G (2006) Free Radical Res 40:1029

    Article  CAS  Google Scholar 

  88. Fraga CG, Martino VS, Ferraro GE, Coussio JD, Boveris A (1987) Biochem Pharmacol 36:717

    Article  CAS  Google Scholar 

  89. Baba S, Osakabe N, Yasuda A, Natsume M, Takizawa T, Nakamura T, Terao J (2000) Free Radical Res 33:635

    Article  CAS  Google Scholar 

  90. Richelle M, Tavazzi I, Enslen M, Offord E (1999) Eur J Clin Nutr 53:22

    Article  CAS  Google Scholar 

  91. Baba S, Osakabe N, Natsume M, Terao J (2002) Free Radic Biol Med 33:142

    Article  CAS  Google Scholar 

  92. Da Silva EL, Piskula M, Terao J (1998) Free Radic Biol Med 24:1209

    Article  Google Scholar 

  93. Natsume M, Osakabe N, Oyama M, Sasaki M, Baba S, Nakamura Y, Osawa T, Terao J (2003) Free Radic Biol Med 34:840

    Article  CAS  Google Scholar 

  94. Baba S, Osakabe N, Natsume M, Muto Y, Takizawa T, Terao J (2001) J Agric Food Chem 49:6050

    Article  CAS  Google Scholar 

  95. Corder R, Mullen W, Khan NQ, Marks SC, Wood EG, Carrier MJ, Crozier A (2006) Nature 444:56

    Article  CAS  Google Scholar 

  96. St. Leger AS, Cochrane AL, Moore F (1979) Lancet 1:1017

    Article  Google Scholar 

  97. Renauld S, de Lorgeril M (1992) Lancet 339:1523

    Article  Google Scholar 

  98. Hertog MG, Feskens EJ, Hollman PC, Katan MB, Krombout D (1993) Lancet 343:1007

    Article  Google Scholar 

  99. Crozier A, Jaganath IB, Clifford MN (2009) Nat Prod Rep 26:1001

    Article  CAS  Google Scholar 

  100. Aron P, Kennedy JA (2008) Mol Nutr Food Res 52:79

    Article  CAS  Google Scholar 

  101. Ottaviani JI, Actis-Goretta L, Villordo JJ, Fraga CG (2006) Biochimie 88:359

    Article  CAS  Google Scholar 

  102. Spencer JPE, Schroeter H, Rechner AR, Rice-Evans C (2001) Antioxid Redox Signal 3:1023

    Article  CAS  Google Scholar 

  103. Surh YJ, Chun KS, Cha HH, Han SS, Keum YS, Park KK, Lee SS (2001) Mutat Res 480:243

    Google Scholar 

  104. Ramljak D, Romanczyk LJ, Metheny-Barlow LJ, Thompson N, Knezevic V, Galperin M, Ramesh A, Dickson RB (2005) Mol Cancer Ther 4:537

    Article  CAS  Google Scholar 

  105. Chul Park Y, Rimbach G, Saliou C, Valacchi G, Packer L (2000) FEBS Lett 465:93

    Article  Google Scholar 

  106. Vestraeten SV, Hammerstone JF, Keen KL, Fraga CG, Oteiza PI (2005) J Agric Food Chem 53:5041

    Article  CAS  Google Scholar 

  107. Beecher GR (2004) Pharm Biol 42:S2

    Article  Google Scholar 

  108. Ito H, Kobayashi E, Li SH, Hatano T, Sugita D, Kubo N, Shimura S, Itoh Y, Tokuda H, Nishino H, Yoshida T (2002) J Agric Food Chem 50:2400

    Article  CAS  Google Scholar 

  109. Lin JK, Weng MS, Grotewold E (eds) (2006) The science of flavonoids. Springer, New York

    Google Scholar 

  110. Rein D, Paglieroni TG, Pearson DA, Wun T, Schmitz HH, Gosselin R, Keen CL (2000) J Nutr 130:2120S

    CAS  Google Scholar 

  111. Pearson DA, Paglieroni TG, Rein D, Wun T, Schramm DD, Wang JF, Holt RR, Gosselin R, Schmitz HH, Keen CL (2002) Thromb Res 106:191

    Article  CAS  Google Scholar 

  112. Nishida S, Satoh H (2003) Mechanisms for the vasodilation induced by Gingko biloba extract and its main consitituent, bilobide in rat aorta. Life Sci 72:2659

    Article  CAS  Google Scholar 

  113. Reed J (2002) Crit Rev Food Sci Nutr 42:S301

    Article  Google Scholar 

  114. Sato M, Maulik N, Das DK (2002) Ann NY Acad Sci 957:122

    Article  CAS  Google Scholar 

  115. Bagchi D, Sen CK, Ray SD, Das DK, Bagchi M, Preuss HG, Vinson JA (2003) Mut Res 523–524:87

    Google Scholar 

  116. Winston D, Graff A, Brinckmann J, Länger R, Turner A, Reich E, Bieber A, Howell A, Romm AJ, Upton R (eds) (2002) American herbal pharacopoeia and therapeutic compendium. American Herbal Pharmacopoeia, Santa Cruz

    Google Scholar 

  117. Howell AB (2002) Crit Rev Food Sci Nutr 42:S273

    Article  Google Scholar 

  118. Sharon N, Ofek I (2002) Crit Rev Food Sci Nutr 42:S267

    Article  Google Scholar 

  119. Pérez-Jiménez J, Arranz S, Saura-Calixto F (2009) Food Res Int 42:1381

    Article  CAS  Google Scholar 

  120. Fogliano V, Corollaro ML, Vitaglione P, Napolitano A, Ferracane R (2011) Mol Nutr Food Res 55:S44

    Article  CAS  Google Scholar 

  121. Haslam E (1998) Practical polyphenolics: from structure to molecular recognition and physiological action. Cambridge University Press, Cambridge

    Google Scholar 

  122. Chung KT, Wong TY, Wei CI, Huang YW, Lin Y (1998) Crit Rev Food Sci Nutr 38:421

    Article  CAS  Google Scholar 

  123. Butler LG (1996) Effect of condensed tannin on animal nutrition. Plenum Press, New York

    Google Scholar 

  124. Lamuela-Raventós RM, Romero-Pérez AI, Andrés-Lacueva C, Tornero A (2005) Food Sci Tech Int 11:159

    Article  CAS  Google Scholar 

  125. Ramiro-Puig E, Casadesus G, Lee H, Zhu X, McShea A, Perry G (2009) Eur J Nutr 48:54

    Article  CAS  Google Scholar 

  126. Skibola CF, Smith M (2000) Free Radic Biol Med 29:375

    Article  CAS  Google Scholar 

  127. Mennen LI, Walker R, Bennetau-Pelissero C, Scalbert A (2005) Am J Clin Nutr 81:326S

    CAS  Google Scholar 

  128. Shoji T, Akazome Y, Kanada T, Ikeda M (2004) Food Chem Toxicol 42:959

    Article  CAS  Google Scholar 

  129. Yance DR, Sagar SM (2006) Integr Cancer Ther 5:9

    Article  CAS  Google Scholar 

  130. Salunkhe DK, Chavan JK, Kadam SS (1990) Dietary tannins: consequences and remedies. CRC Press, Boca Raton

    Google Scholar 

  131. Hervas G, Perez V, Giraldez FJ, Mantecon AR, Almar MM, Frutos P (2003) J Comp Pathol 129:44

    Article  CAS  Google Scholar 

  132. Brueggemeier R, Richards JA, Joomprabutra S, Bhat AS, Whetstone JL (2001) J Steroid Biochem Mol Biol 79:75

    Article  CAS  Google Scholar 

  133. Chen S, Sun XZ, Kao YC, Kwon A, Zhou D, Eng E (1998) Pharm Biol 36:53

    Article  Google Scholar 

  134. Bentivegna SS, Whitney KM (2002) Food Chem Toxicol 40:1731

    Article  CAS  Google Scholar 

  135. Wren AF, Cleary M, Frantz C, Melton S, Norris L (2002) J Agric Food Chem 50:2180

    Article  CAS  Google Scholar 

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Rusconi, M., Pinorini, M.T., Conti, A. (2013). Proanthocyanidins of Cocoa: Bioavailability and Biological Activities. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_77

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