Prof Alan Crozier, Professor of Plant Biochemistry and Human Nutrition, University of Glasgow speaks to the Glasgow Southern Medical Society on the benefits of a diet rich in phytoantioxidants.

1. Healthy Eating & Drinking Alan Crozier Institute of Biomedical and Life Sciences University of Glasgow Scotland, UK Professor of Plant Biochemistry and Human Nutrition

2. FRUITS AND VEGETABLES CONTAIN: minerals, fibre, vitamins and phytochemicals

3. Common C 6 -C 3 -C 6 Flavonoid Structures

4. Structures of Common Dietary Phenolics O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O H O H O O H O H E l l a g i c a c i d S a n g u i i n H - 1 0 ( E l l a g i t a n n i n - h y d r o l y s a b l e t a n n i n )‏ H O H O H O O H H O O H H O O H O H H O H O O H O H O H O H H O H O H O O H H O O H O H O H O H O H H O O H O H C O O H G a l l i c a c i d O H O H H O H O H O O H t r a n s - R e s v e r a t r o l - 3 - O - g l u c o s i d e ( S t i l b e n e )‏ O H O H O H H O O C O H O H 5 - O - C a f f e o y l q u i n i c a c i d ( c h l o r o g e n i c a c i d )‏ ( H y d r o x y c i n n m a t e )‏ H O H O O H O H H O H O O H O H P r o c y a n i d i n t r i m e r C 2 ( C o n d e n s e d t a n n i n )‏ O H O H H O H O O H O H O H E U T U

7. Healthy Supplements to a 5-a-Day Diet Red wine - lots of phenolics, 3 glasses per day because of alcohol Green tea - rich in flavan-3-ol monomers Cocoa - rich in flavan-3-ol monomers and procyanidins - problem - fats Fruit juices - varied phenolics - sugar limits intake Nuts with the skin - contain vitamin E, flavonoids and fats (salt)‏ Black tea - lots of thearubigins - with or without milk ? Berries - raspberries, blueberries, blackberries, strawberries etc

8. UK UK UK UK UK Mal Two-three pieces of chocolate per day !

9. Theobroma cacao, otherwise known as cocoa Seeds from the pods are roasted and used to make cocoa and chocolate Chocolate and cocoa are rich sources of flavan-3-ol monomers (catechins) and polymers (procyanidins) which are strong antioxidants but also contain unsaturated fats

10. Cocoa and chocolate contain monomeric and polymeric flavan-3-ols Protective Effects of Flavan-3-ol-Rich Cocoa Improves vascular health reduced platelet aggregation enhanced vasodilation - reduced blood pressure Kuna Indians San Blas Island 4 cups cocoa per day with age minimal increase in blood pressure reduced hypertension and other CDVs Kuna Indians Panama City 6-fold lower cocoa intake with age increased in blood pressure hypertension and other CDVs Schroeter et al. PNAS 103, 1024-9, 2006 Zutphen Study Reduced blood pressure 50% decreased risk of CVD

11. 0 5 10 15 20 25 30 milk (20 - 34% cocoa)‏ dark (70 - 85% cocoa )‏ cocoa (100%)‏ 35 procyanidin content (µmol/g)‏ Procyanidin Content Different Types of Chocolate (Roger Corder)‏

13. Red Wines, Procyanidins and Inhibition of Endothelin-1 Synthesis Corder et al. Nature, 30 November 2006

14. French 1999 Census - Regional Male Longevity Corder et al. Nature, 30 November 2006

15. In Midi-Pyrenees, South West France………. Red wines, mainly for local consumption, made from Tannat grapes – small, lots of seeds, and, therefore, rich in procyanidins Traditional methods of wine making, 28 day vinification, so seeds extracted and Madiran wine contains high levels of procyanidins Big regional variations in CHD in France. In Midi-Pyrenees, 1999 French census shows 33% more men over 75 years of age and more than double the number over 90 years of age than the French average Similar evidence of longevity in Nuoro province of Sardinia where procyanidin-rich wines are produced, mainly for local consumption

16. “ The potential health benefits of tea consumption are well known ”

17. Young first flush tea ( Camellia sinensis ) shoots ready for plucking

18. Green Tea Flavan-3-ol Structures

19. O O O H O H O H O R T h e a r u b i g i n n Thearubigins are complex polymers of catechins with unknown structure Principle phenolics in black tea

20. Major Phenolic Compounds in Green and Black Tea infusions

21. Fruit and Vegetable Juices……………. A convenient supplement to 5-a-day F & V or a busy lifestyle and less than 5-a-day Fruit and vegetable drinks may be as effective as consumption of fruit and vegetables in relation to a reduced risk of chronic disease Ruxton et al. Int. J. Food Sci. Nutr. 2006 Kame Project Long-term consumption of fruit and vegetable juices can reduce the incidence of Alzheimer’s disease by 75% Dia et al. Am. J. Medicine 119 , 751-9, 2006 Which juices?.....

22. UK a UK UK UK UK Antioxidant Activity of Commercial Fruit Juices

23. UK a UK Phenolic Compounds in UK Commercial Fruit Juices

24. Combination of Fruit Juices Providing High Antioxidants and Diversity of Phenolic Compounds Purple grape - flavonols, hydroxycinnmates, procyanidins, anthocyanins Cranberry - flavonols, procyanidins Citrus - flavanones Cloudy apple - hydroxycinnamates, flavan-3-ol monomers, procyanidins, hydroxychalcones Pomegranate ? - anthocyanins, ellagitannins

25. To what extent are the various dietary phenolics bioavailable ? What is bioavailability ?

26. Possible Routes for Consumed Dietary Phenolics in Humans Dietary phenolics Tissues Small intestine LIVER Colon bile Kidney General circulation Urine Faeces Ileostomy bag

27. The fate of strawberry phenolics in humans with a colon Human volunteers ingested 200 g of strawberries with paracetamol and lactulose Plasma and urine collected at several time points over a 24 h period All samples analysed by HPLC-PDA-MS 2 to determine the fate of anthocyanins

28. The fate of strawberry anthocyanins in humans with a colon - with and without cream

29. Pelargonidin-3-Glucuronide In Plasma After Ingestion of 200 g of Strawberries 50 100 150 200 250 300 0 5 10 15 20 25 Time (h)‏ nmol/L With 100 mL double cream Without cream

30. Absorption and Metabolism of Strawberry and Blackberry Anthocyanins (1% of intake)‏

31. Colonic degradation of anthocyanins (Aura et al., Eur J Nutr 44 , 133-142, 2005)‏

32. Flavonol Glycosides 200 g fried onions - 257  moles 300 mL tomato juice- 176  moles

33. Quercetin-4-Glucoside Metabolites In Plasma A 0 200 400 600 800 0 1 2 3 4 5 6 Time (h)‏ Conc. nmoles/L Quercetin-3'-sulphate Quercetin-3-glucuronide B 25 50 75 100 125 0 1 2 3 4 5 6 Time (h)‏ Conc. nmoles/L 0 Quercetin glucuronide sulphate Isorhamnetin-3-glucuronide Quercetin diglucuronide

34. Flavonol Glycosides 200 g fried onions - 257  moles 300 mL tomato juice- 176  moles

35. 0 2 4 6 8 10 12 14 16 0 1 2 3 4 5 6 7 8 Time (h)‏ Concentration (nmoles/L)‏ Quercetin-3-glucuronide Isorhamnetin-3-glucuronide Quercetin-3-Rutinoside Metabolites In Plasma

36. Fate of Rutin In The Large Intestine

37. Possible Routes for Consumed Dietary Phenolics in Humans Dietary phenolics Tissues Small intestine LIVER Colon bile Kidney General circulation Urine Faeces Ileostomy bag