Polyphenolic and hydroxycinnamate contents of whole coffee fruits from China, India, and Mexico

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 22, 2013, Pages 5298-5309

  Mullen, W ^a   Nemzer, B ^b   Stalmach, A ^a   Ali, S ^a   Combet, E ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b FutureCeuticals Inc   (United States)

Author keywords

caffeine; chlorogenic acid; procyanidins; quercetin; total flavonol; total phenol and antioxidant

Indexed keywords

CHLOROGENIC ACIDS; PROCYANIDINS; QUERCETIN; TOTAL FLAVONOL; TOTAL PHENOLS;

CAFFEINE; COFFEE; FATTY ACIDS; FRUITS; MASS SPECTROMETRY; PHENOLS;

FLAVONOIDS;

ANTIOXIDANT; CINNAMIC ACID DERIVATIVE; FLAVONOL DERIVATIVE; POLYPHENOL;

ARTICLE; CHEMISTRY; CHINA; COFFEE; COMPARATIVE STUDY; DIET SUPPLEMENTATION; ECONOMICS; FOOD INDUSTRY; FRUIT; FUNCTIONAL FOOD; GROWTH, DEVELOPMENT AND AGING; HYDROXYLATION; INDIA; INDUSTRIAL WASTE; MEXICO; PLANT SEED; SURFACE PROPERTY;

ANTIOXIDANTS; CHINA; CINNAMATES; COFFEA; DIETARY SUPPLEMENTS; FLAVONOLS; FOOD-PROCESSING INDUSTRY; FRUIT; FUNCTIONAL FOOD; HYDROXYLATION; INDIA; INDUSTRIAL WASTE; MEXICO; POLYPHENOLS; SEEDS; SURFACE PROPERTIES;

EID: 84878652485     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4003126     Document Type: Article

References (68)

1. Clifford, M. N. Chlorogenic acids-Their complex nature and routine determination in coffee beans Food Chem. 1979, 4, 63-71 (Pubitemid 9116593)
2. Clifford, M. N. Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden J. Sci. Food Agric. 1999, 79, 362-372 (Pubitemid 29150578)
3. Fisher, H. O. L.; Dangschat, G. Konstitution der Chlorogensaure (3. Metteil. Uber Chinasaure und Derivate) Ber. Dtsch. Chem. Ges. A/B 1932, 65, 1037-1040
4. Robiquet, P.-J.; Boutron, A.-F. Ueber den Kaffee. In Annalen der Pharmacie; Liebig, J.; Merck, E.; Mohr, F.; Coblenz, Eds.; Wiley: Germany, 1837; Vol. 23-24, pp 93-95.
5. Payen, S. Memoire sur le café C. R. Acad. Sci. 1846, 23, 244-251
6. Trugo, L. C.; Macrae, R. Chlorogenic acid composition of instant coffees Analyst 1984, 109, 263-266
7. Jaiswal, R.; Matei, M. F.; Golon, A.; Witt, M.; Kuhnert, N. Understanding the fate of chlorogenic acids in coffee roasting using mass spectrometry based targeted and non-targeted analytical strategies Food Funct. 2012, 3, 976-984
8. Farah, A.; De Paulis, T.; Trugo, L. C.; Martin, P. R. Effect of roasting on the formation of chlorogenic acid lactones in coffee J. Agric. Food Chem. 2005, 53, 1505-1513 (Pubitemid 40322144)
9. Singleton, V. L.; Rossi, J. A. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic reagents Am. J. Enol. Vitic. 1965, 16, 144-158
10. Chang, C. C.; Yang, M. H.; Wen, H.-M.; Chern, J.-C. Estimation of total flavonoid content in Propolis by two complementary colorimetric methods J. Food Drug Anal. 2002, 10, 178-182 (Pubitemid 35355995)
11. Benzie, I. F. F.; Strain, J. J. The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": The FRAP assay Anal. Biochem. 1996, 239, 70-76
12. n identification of chlorogenic acids J. Agric. Food Chem. 2003, 51, 2900-2911
13. n J. Agric. Food Chem. 2005, 53, 3821-3832 (Pubitemid 40936729)
14. n of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids J. Agric. Food Chem. 2006, 54, 1957-69
15. Santos-Buelga, C.; Franciaaricha, E. M.; Escribano-Bailon, M. T. Comparative flavan-3-ol composition of seeds from different grape varieties Food Chem. 1995, 53, 197-201
16. Jaiswal, R.; Jayasinghe, L.; Kuhnert, N. Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS J. Mass Spectrom. 2012, 47, 502-15
17. n analysis of phenolic compounds and purine alkaloids in green and black tea J. Agric. Food Chem. 2004, 52, 2807-2815
18. Appeldoorn, M. M.; Vincken, J.-P.; Sanders, M.; Hollman, P. C.; Gruppen, H. Combined normal-phase and reversed-phase liquid chromatography/ESI-MS as a tool to determine the molecular diversity of A-type procyanidins in peanut skins J. Agric. Food Chem. 2009, 57, 6007-6013
19. Prior, R. L.; Lazarus, S. A.; Cao, G. H.; Muccitelli, H.; Hammerstone, J. F. Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry J. Agric. Food Chem. 2001, 49, 1270-1276 (Pubitemid 32884947)
20. Mullen, W.; Marks, S. C.; Crozier, A. Evaluation of phenolic compounds in commercial fruit juices and fruit drinks J. Agric. Food Chem. 2007, 55, 3148-3157 (Pubitemid 46668329)
21. Marks, S. C.; Mullen, W.; Crozier, A. Flavonoid and chlorogenic acid profiles of English cider apples J. Sci. Food Agric. 2007, 87, 719-728 (Pubitemid 46374851)
22. IUPAC Nomenclature of cyclitols Biochem. J. 1976, 153, 23-31
23. n: identification of seven New classes of compounds J. Agric. Food Chem. 2010, 58, 8722-8737
24. Crozier, A.; Jaganath, I. B.; Clifford, M. N. Dietary phenolics: chemistry, bioavailability and effects on health Nat. Prod. Rep. 2009, 26, 1001-1043
25. Clifford, M. N. Chlorogenic acids and other cinnamates-nature, occurrence, dietary burden, absorption and metabolism J. Sci. Food Agric. 2000, 80, 1033-1043 (Pubitemid 30319397)
26. Mullen, W.; Nemzer, B.; Ou, B.; Stalmach, A.; Hunter, J.; Clifford, M. N.; Combet, E. The antioxidant and chlorogenic acid profiles of whole coffee fruits are influenced by the extraction procedures J. Agric. Food Chem. 2011, 59, 3754-62
27. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Gebhardt, S.; Prior, R. L. Concentrations of proanthocyanidins in common foods and estimations of normal consumption J. Nutr. 2004, 134, 613-7 (Pubitemid 38298505)
28. De Colmenares, N. G.; Ramirez-Martinez, J. R.; Aldana, J. O.; Clifford, M. N. Analysis of proanthocyanidins in coffee pulp J. Sci. Food Agric. 1994, 65, 157-162
29. Joet, T.; Laffargue, A.; Descroix, F.; Doulbeau, S.; Bertrand, B.; kochko, A. d.; Dussert, S. Influence of environmental factors, wet processing and their interactions on the biochemical composition of green Arabica coffee beans Food Chem. 2010, 118, 693-701
30. Farris, P. Idebenone, green tea, and Coffeeberry extract: new and innovative antioxidants Dermatol. Ther. 2007, 20, 322-9 (Pubitemid 350197163)
31. Henry-Vitrac, C.; Ibarra, A.; Roller, M.; Merillon, J. M.; Vitrac, X. Contribution of chlorogenic acids to the inhibition of human hepatic glucose-6-phosphatase activity in vitro by Svetol, a standardized decaffeinated green coffee extract J. Agric. Food Chem. 2010, 58, 4141-4
32. Ochiai, R.; Jokura, H.; Suzuki, A.; Tokimitsu, I.; Ohishi, M.; Komai, N.; Rakugi, H.; Ogihara, T. Green coffee bean extract improves human vasoreactivity Hypertens. Res. 2004, 27, 731-7 (Pubitemid 40045512)
33. Watanabe, T.; Arai, Y.; Mitsui, Y.; Kusaura, T.; Okawa, W.; Kajihara, Y.; Saito, I. The blood pressure-lowering effect and safety of chlorogenic acid from green coffee bean extract in essential hypertension Clin. Exp. Hypertens. 2006, 28, 439-49 (Pubitemid 44034669)
34. Farah, A.; Monteiro, M.; Donangelo, C. M.; Lafay, S. Chlorogenic acids from green coffee extract are highly bioavailable in humans J. Nutr. 2008, 138, 2309-15
35. Gonthier, M. P.; Remesy, C.; Scalbert, A.; Cheynier, V.; Souquet, J. M.; Poutanen, K.; Aura, A. M. Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro Biomed. Pharmacother. 2006, 60, 536-40 (Pubitemid 44740368)
36. Monteiro, M.; Farah, A.; Perrone, D.; Trugo, L. C.; Donangelo, C. Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans J. Nutr. 2007, 137, 2196-201 (Pubitemid 47529576)
37. Stalmach, A.; Steiling, H.; Williamson, G.; Crozier, A. Bioavailability of chlorogenic acids following acute ingestion of coffee by humans with an ileostomy Arch. Biochem. Biophys. 2010, 501, 98-105
38. dos Santos, M. D.; Martins, P. R.; dos Santos, P. A.; Bortocan, R.; Iamamoto, Y.; Lopes, N. P. Oxidative metabolism of 5- O -caffeoylquinic acid (chlorogenic acid), a bioactive natural product, by metalloporphyrin and rat liver mitochondria Eur. J. Pharm. Sci. 2005, 26, 62-70 (Pubitemid 41097262)
39. Dupas, C.; Marsset Baglieri, A.; Ordonaud, C.; Tome, D.; Maillard, M. N. Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study Mol. Nutr. Food Res. 2006, 50, 1053-60 (Pubitemid 44861501)
40. Lafay, S.; Gil-Izquierdo, A.; Manach, C.; Morand, C.; Besson, C.; Scalbert, A. Chlorogenic acid is absorbed in its intact form in the stomach of rats J. Nutr. 2006, 136, 1192-7
41. Lafay, S.; Morand, C.; Manach, C.; Besson, C.; Scalbert, A. Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats Br. J. Nutr. 2006, 96, 39-46 (Pubitemid 44160894)
42. Rodriguez de Sotillo, D. V.; Hadley, M. Chlorogenic acid modifies plasma and liver concentrations of: cholesterol, triacylglycerol, and minerals in (fa/fa) Zucker rats J. Nutr. Biochem. 2002, 13, 717-726 (Pubitemid 35463200)
43. Bassoli, B. K.; Cassolla, P.; Borba-Murad, G. R.; Constantin, J.; Salgueiro-Pagadigorria, C. L.; Bazotte, R. B.; da Silva, R. S.; de Souza, H. M. Chlorogenic acid reduces the plasma glucose peak in the oral glucose tolerance test: effects on hepatic glucose release and glycaemia Cell Biochem. Funct. 2008, 26, 320-8 (Pubitemid 351613172)
44. Konishi, Y.; Kobayashi, S. Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers J. Agric. Food Chem. 2004, 52, 2518-26
45. Zhao, Y.; Wang, J.; Ballevre, O.; Luo, H.; Zhang, W. Antihypertensive effects and mechanisms of chlorogenic acids Hypertens. Res. 2011, 35, 370-374
46. Suzuki, A.; Kagawa, D.; Ochiai, R.; Tokimitsu, I.; Saito, I. Green coffee bean extract and its metabolites have a hypotensive effect in spontaneously hypertensive rats Hypertens. Res. 2002, 25, 99-107 (Pubitemid 34196302)
47. Kahle, K.; Huemmer, W.; Kempf, M.; Scheppach, W.; Erk, T.; Richling, E. Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption J. Agric. Food Chem. 2007, 55, 10605-10614
48. Onakpoya, I.; Terry, R.; Ernst, E. The use of green coffee extract as a weight loss supplement: A systematic review and meta-analysis of randomised clinical trials. Gastroenterol. Res. Pract. 2011, 2011, DOI: 10.1155/2011/382852.
49. van Dam, R. M.; Willett, W. C.; Manson, J. E.; Hu, F. B. Coffee, caffeine, and risk of type 2 diabetes: a prospective cohort study in younger and middle-aged U.S. women Diabetes Care 2006, 29, 398-403 (Pubitemid 44106525)
50. Wadge, A. Food Standard Agency's advice on caffeine BMJ 2009, 338, b299
51. Crozier, T. W. M.; Stalmach, A.; Lean, M. E. J.; Crozier, A. Espresso coffees, caffeine and chlorogenic acid intake: potential health implications Food Funct. 2012, 3, 30-33
52. IFIC Caffeine and Health: Clarifying the controversies. http://www.foodinsight.org/Content/3147/Caffeine-v8-2.pdf.
53. Delfiol, D. J. Z.; Oliveira, J. P.; Casalecchi, F. L.; Kievitsbosch, T.; Hussni, C. A.; Riet-Correa, F.; Araujo, J. P.; Borges, A. S. Equine poisoning by coffee husk (Coffea arabica L.). BMC Vet. Res. 2012, 8, DOI: 10.1186/1746-6148-8-4.
54. Ramalakshmi, K.; Raghavan, B. Caffeine in coffee: its removal. Why and how? Crit. Rev. Food Sci. Nutr. 1999, 39, 441-456
55. Clifford, M. N.; Ramirez-Martinez, J. R. Tannins in wet-processed coffee beans and coffee pulp Food Chem. 1991, 40, 191-200
56. Vincent, J. C. Green Coffee Processing. In Coffee; Clarke, R. J.; Macrae, R., Eds.; Springer: The Netherlands, 1987; pp 1-33.
57. Gonzalez-Rios, O.; Suarez-Quiroz, M. L.; Boulanger, R.; Barel, M.; Guyot, B.; Guiraud, J.-P.; Schorr-Galindo, S. Impact of "ecological" post-harvest processing on the volatile fraction of coffee beans: I. Green coffee J. Food Compos. Anal. 2007, 20, 289-296 (Pubitemid 46217453)
58. Spradling, V. B. Phenolics in Red Wine Pomace and Their Potential Application in Animal and Human Health; University of Missouri, Kansas City, MO, 2008.
59. Cardona, J. A.; Wysocki, A. F.; Talcott, S. T. Economic analysis of an isolated product obtained from Muscadine grape pomace Horttechnology 2010, 20, 160-168
60. Makris, D. P.; Boskou, G.; Andrikopoulos, N. K. Polyphenolic content and in vitro antioxidant characteristics of wine industry and other agri-food solid waste extracts J. Food Compos. Anal. 2007, 20, 125-132 (Pubitemid 44793707)
61. Shrikhande, A. J. Wine by-products with health benefits Food Res. Int. 2000, 33, 469-474 (Pubitemid 30427826)
62. Ena, A.; Pintucci, C.; Carlozzi, P. The recovery of polyphenols from olive mill waste using two adsorbing vegetable matrices J. Biotechnol. 2012, 157, 573-577
63. Bhushan, S.; Kalia, K.; Sharma, M.; Singh, B.; Ahuja, P. S. Processing of apple pomace for bioactive molecules Crit. Rev. Biotechnol. 2008, 28, 285-296
64. Tow, W. W.; Premier, R.; Jing, H.; Ajlouni, S. Antioxidant and antiproliferation effects of extractable and non-extractable polyphenols isolated from apple waste using different extraction methods J. Food Sci. 2012, 76, T163-T172
65. Tomaino, A.; Martorana, M.; Arcoraci, T.; Monteleone, D.; Giovinazzo, C.; Saija, A. Antioxidant activity and phenolic profile of pistachio (Pistacia vera L., variety Bronte) seeds and skins Biochimie 2010, 92, 1115-1122
66. Andrade, K. S.; Goncalvez, R. T.; Maraschin, M.; Ribeiro-do-Valle, R. M.; Martinez, J.; Ferreira, S. R. Supercritical fluid extraction from spent coffee grounds and coffee husks: antioxidant activity and effect of operational variables on extract composition Talanta 2012, 88, 544-52
67. Murthy, P.; Naidu, M. M. Recovery of phenolic antioxidants and functional compounds from coffee industry by-products Food Bioprocess. Technol. 2012, 5, 897-903
68. Edwards, C.; Garcia, A.; Combet, E. Colonic Metabolism of Bioactive Molecules; Potential Impact of Dietary Fiber. In Dietary Fiber and Health; Cho, S.; Almeida, N., Eds.; CRC Press: Boca Raton, FL, 2012; pp 209-233.