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Beyond Caffeine. Unexplored Potentiality of other Coffee Compounds

Beyond Caffeine. Unexplored Potentiality of other Coffee Compounds. Luciano Navarini Research & Scientific Coordination luciano.navarini@illy.com. German Research School J ü lich, 25 August 2010. Coffee & Health. 90% of medical research on coffee is focussed on caffeine.

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Beyond Caffeine. Unexplored Potentiality of other Coffee Compounds

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  1. Beyond Caffeine. Unexplored Potentiality of other Coffee Compounds Luciano Navarini Research & Scientific Coordination luciano.navarini@illy.com German Research School Jülich, 25 August 2010

  2. Coffee & Health 90% of medical research on coffee is focussed on caffeine

  3. Caffeine therapeutic prospects (Daly, Cell. Mol. Life Sci. 2007) • Alzheimer’s disease • Asthma – Antiinflammatories • Behavior targets – Antidepressant – Anxiolytic – Cognitive enhancement – Neuroprotection • Cancer • Diabetes (type 2) • Pain • Parkinson’s disease • Renal effects – Diuretics • Respiratory targets – Antitussives – Apnea – Chronic obstructive pulmonary disease Adenosine receptor antagonist – Phosphodiesterase inhibitor – G2 checkpoint inhibitor – Phosphoenolpyruvate carboxykinase inhibitor – Di-peptidyl peptidase IV inhibitor

  4. However many studies suggest that some coffee properties and coffee physiological effects are not strictly related to caffeine e.g. antioxidant activity Caffeine is a free radical scavenger (Parras et al, 2007, Devasagayam et al., 1996, ) however it cannot be the only antioxidant present Dorea & da Costa, Br. J. Nutr. 2005; Ranheim & Halvorsen, Mol. Nutr. Food Res. 2005

  5. very high antioxidant activity Pellegrini et al. J. Nutr. 2003

  6. Something else? > 1500 chemical compounds

  7. 1.0 % Trigonelline 5.1% Acids & Polyphenols 1.3 % Caffeine 4.5% Minerals 38 % Carbohydrates 33 % Melanoidins 17 % Lipids in particular…

  8. Carbohydrates 3 types of polysaccharides: type II arabinogalactans, galactomannans, (cellulose), Major components (62%) of the soluble dietary fiber (SDF) complex isolated from coffee brews Fermented by human intestinal microbiota (Short-Chain Fatty Acids)   0.5 g – 0.7 of SDF Dietary fiber intake: 7 g/day (Spain) 14 g/day (USA) 20 g/day (Germany) Diaz-Rubio & Saura-Calixto, 2007; Gniechwitz et al.2007, 2008, Reichardt et al., 2009

  9. Carbohydrates Oligosaccharides: several present in coffee brews (di-, tri, up to esa- containing Man, Gal, Ara, Rha ecc. in variable amount) Several studies on mannooligosaccharides isolated from coffee as prebiotic and actually used in japanese instant coffee products

  10. Acids & Polyphenols

  11. Hydroxycinnamic acids g/mL in coffee brews antioxidant, antiinflammatory, antimutagenic CA = Caffeic acid FA = Ferulic acid pCoA = p-Coumaric Acid (Devipriya et al., 2008) are widely present, mainly in esterified form,in: (Nardini et al., 2002)

  12. Very high alkyl peroxyl radical scavenger activity Protective effect of apples against cancer Chlorogenic acids In green coffee beans (C. arabica) 3(5)-caffeoylquinic acid • mg/mL in coffee brews • up to 1g/day intake Sawa et al., 1999; Boyer & Liu 2004;

  13. by roasting, conversion to quinides 3,4-diferuloyl-1,5-quinide J. Nutr. (2003) 133, 3529

  14. Chlorogenic acid – Caffeine complex low binding energy  20 – 25 % bound caffeine Physiological effects ? Other complexes ? Horman & Viani, 1971;1972; D’Amelio et al., 2009

  15. Isoflavonoids & Lignans (phyto-oestrogens) Mazur et al., Br. J. Nutr., 1998. Isoflavonoids & Lignans possess several biological activities, such as antioxidant and (anti)oestrogenic properties, and thus may reduce the risk of certain cancers as well as cardiovascular diseases (Milder et al, 2005; Osoki & Kennelly 2003)

  16. Isoflavones Moderate consuption of 3-5 EC cups/day (arabica/robusta blend 70/30) = isoflavone ingestion of 300 – 500 μg/day soy & soy products 0.1 – 3.0 mg/g; apple = broccoli = cauliflower 0.1 μg/g Alves et al., 2010

  17. Lignans Milder et al. Br. J. Nutr 2005

  18. Milder et al.J. Nutr,. 2005

  19. Proteins Carbohydrates Phenolics Melanoidins Macromolecular, nitrogenous, brown-colored Maillard reaction end-products formed during home and industrial heat processing of foods, widely distributed in our diet (coffee, cocoa, bread, malt, honey...) Proteins non-enzymatic browning Phenolics Carbohydrates

  20. Melanoidins: easy to recognize

  21. Modified proteins containing low Mw chromophores able to crosslink proteins via -amino groups AA. Hofmann, Eur.Food Res.Tecnol., 1998 A skeleton made up of polymerized sugar degradation products, formed in the early stages of Maillard reaction Polymers built up of repeating units of furans and/or pyrroles formed during advanced stages of Maillard reaction Tressl et al.J.A.F.C.,. 1998 Caemmerer et al.J.A.F.C.,. 2002 Melanoidins: challenging chemistry

  22. Coffee Brew LMw Fractions < 3 KDa IMw Fractions HMw Fractions >10-15 KDa Coffee melanoidins dialysis/diafiltration/ultrafiltration • Antioxidant activity (Daglia et al.,2008; Delgado-Andrade et al, 2005; Nicoli et al., 1997; Manzocco et al., 2001) • Metal-chelating properties (Wen et al., 2005; Rufian-Henares & de la Cueva, 2009; Homma & Murata, 1995) • Antimicrobial activity (Rufian-Henares & Morales, 2008; Daglia et al., 1994 and 1998) • Antihypertensive activity (Rufian-Henares & Morales, 2007) • Antimutagenic activity (Powrie et al., 1983) • Partially degraded by the human gut bacteria (Reichardt et al. 2009)

  23. Melanoidin Melanoidin Fe3+ Fe3+ Fe3+ Fe3+ Fe3+ Mg2+ Fe3+ Mg2+ Mg2+ Fe3+ Fe3+ Fe3+ Mg2+ Melanoidin Melanoidin Melanoidin Siderophore Siderophore Siderophore Mechanisms of antimicrobial activity OUTSIDE INSIDE (Microbial cell) Membrane Disruption Iron Starvation Melanoidin Siderophores Chelation Rufian-Henares & de la Cueva, J. Agric Food Chem. (2009)

  24.  50 – 100 mg Lipids Maier, 1981

  25. Hyper-cholesterolemic Anticarcinogenic Chemopreventive Diterpenes Scandinavian-style boiled coffee Temporary cholesterol increase Filter, instant, espresso, moka Gross et al. 1997; Cavin et al., 2002; Weusten-van der Wouw et al.,1994, Urgert &Katan, 1997, De Roos et al., 2001

  26. Tocopherols (Vitamin E) Very small contribution to the recommended daily Vitamin E intake (15 mg of -tocopherol) Complement to the overall antioxidant effect provided by the brew  = 349 – 825 mg/Kg oil  = 455 - 749 mg/Kg oil  = 31.9 – 113 mg/Kg oil Jham et al.,JAFC (2007) 55 5995  = 1.37 ± 0.47 g  = 2.09 ± 0.67 g Alves et al.,Food Chem (2009) 115, 1549

  27. Phytosterols In green coffee beans (% of sterols) Frega et al.,1993; Speer et al., 1996

  28. J. Nutr. 2009 Trigonelline second most abundant alkaloid in green coffee (C. arabica: 7.9 – 10.6 g/kg; C. canephora: 6.6 – 6.8 g/kg) • antimicrobial agent inhibiting the growth of Streptococcus mutans (dental caries) (Daglia et al., JAFC 2002) • in vitro inhibits the invasion of liver cancer cells (Hirakawa et al, Biosc. Biotechnol. Biochem. 2005) • associated with regeneration of dentrites and axons in cortical neurons in rats (Tohda et al., Neurosignals 2005)

  29. - CO2 N-methylpyridinium - CH3 Nicotinic acid Nicotinamide Methyl nicotinate Niacin = Vitamin B3 (pellagra: niacin deficiency disease) Trigonelline undergoes significant degradation during roasting Aroma compounds (pyridine and pyrrole derivatives)

  30.  2 mg = 17 mg/day = 13 mg/day Niacin 0.617 mol/g 0.029 mol/g 0.028 mol/g 1.323 mol/g 0.047 mol/g 1.426 mol/g 0.023 mol/g 0.158 mol/g Lang et al., J. Agric. Food Chem. (2008)

  31. N-methylpyridinium major food source induction of chemopreventive phase II detoxifying enzyme activities in vitro and in vivo (glutathione S-trasferase; UDP-glucuronyl-trasferase) Somoza et al., J. Agric. Food Chem. (2003)

  32. Coffee brews Monoamine oxidase (MAO) inhibitors B A antidepressants treatment & prevention of Parkinson’s disease Herraiz & Chaparro, 2006, Life Sciences, 78, 795

  33. -Carbolines Monoamine oxidase (MAO) inhibitors ristretto lungo

  34. Minerals • Potassium: relevant source (Gillies & Birkbeck, 1983) • Magnesium: substantial source. A mean of 63.7 g/cup (100 mL) has been reported (Astier-Dumas & Gounelle de Pontanel, 1974) • Manganese:significant contribution (Gillies & Birkbeck, 1983) • Chromium: 8% daily intake (Santos et al., 2004)

  35. Acrylamide A wide range of cooked foods contain the “probably carcinogenic to humans” compound acrylamide 299 – 762* < 2 g/cup Koehler et al * Bagdonaite et al., JAFC 2008

  36. Furan is a potential concern as, based on animal trials, is considered possibly carcinogenic to humans (IARC 1995) Light Dark  5 g/cup Guenther et al, Food Add. & Contam. 2009

  37. PAHs Polycyclic aromatic hydrocarbons potentially carcinogenic, B[a]Peq, in coffee brews (moka) range from 0.008 to 0.060 g/L A maximum level of 5 g/kg in smoked fish and meat (Commission Regulation 2005/208/EC) “coffee contributes with very insignificant quantities to the daily human intake” Orecchio et al., 2009, Food and Chemical Toxicology, 47, 819; Houessou, 2007, PhD Thesis; Houessou et al.,J.Agric. Food Chem. 2007; 2008)

  38. MODERATE CONSUMPTION OF 3-5 CUPS/DAY Risks Benefits not only due to caffeine!

  39. “Many studies support the idea that coffee-drinking has health benefits. Thus it is simple to conceptualise coffee as a functional food” FURTHER RESEARCH: in vivo; melanoidins; caffeine complexation, new compounds…

  40. > 1500 chemical compounds as a function of botanical species, variety, geographical origin, processing, blending, roasting, brewing technique… different taste, flavour, mouthfeel… …but also physiological effects ???

  41. Thank you ! Research as love for the World. Ernesto Illy (1925 – 2008)

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