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NOO - } Oxygen singlet Ref: E.Rock-INRA France 2009 Energy OH - PDF document

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Main class of anti-oxydant ( Polyphenols and catotenoids) of Indogenous fruits Stress antioxydant Polyphenols chemistry and poyphenols classes & Aspects of analysis and main problems Carotenoids chemistry and carotenoids classes

  1. Main class of anti-oxydant ( Polyphenols and catotenoids) of Indogenous fruits Stress antioxydant Polyphenols chemistry and « poyphenols classes » & Aspects of analysis and main problems Carotenoids chemistry and « carotenoids classes » & Aspects of analysis and main problems ORAC interest and Bioavailability … documents Autors presented: E.Rock, Guyot , (Inra Clermont, France), Kimura, M. & Rodriguez-Amaya, D.B. (1999), Brazil; C.Mertz, F.Vaillant ,P.Brat , cirad, France, F.Hau , University Barquisimeto Venezuela. Pictures/ E.Rock. Inra Clermont France antioxidants against oxidative stress Main antioxydants in fruits (ref/E.Rock:Inra Clermont/France ) O 2 NOO - } Oxygen singlet Ref: E.Rock-INRA France 2009 Energy OH° Yellow Blue Red Green White Hydroxyl radical Reactive Orange Purple HOOH Oxygen Species Hydrogen peroxide Lutein Beta-Carotene Allium Vitamin C Anthocyanins Vitamin A ROS Lycopene Vitamin C Zeaxanthin Allicin Bioflavonoids Anthocyanins Phenolics Indoles Vitamin C peroxynitrite Potassium Vitamin K •¯ Potassium The trends are on the study focused on phytochemicals (i.e. polyphenols & carotenoids) rather than Mammals including human beings minerals and vitamins are adapted to live in oxygen containing atmosphere. 1 Radishes Spinach Carrots Oxygen molecule is somewhat unstable and is at the Blueberries Garlic Tomatoes Cabbage Oranges origin of reactive oxygen species Eggplant Onions 3 Strawberries Lettuce Bananas Broccoli Atmospheric oxygen can be easily transformed into reactive species Oxidative stress: biological concept Polyphenols???? ( ref/ Guyot/inra France) (ref/E.Rock:Inra Clermont/France) ROS ANTIOXIDANTS Respiratory chain Enzymes (SOD, Cat., GPx, GR, ...) Polyphénols ( mitochondria ) Proteins (albumin, caeruloplasmin, ferritin, ...) Phenolics compounds Polyphénols Immunity ? Nutrients and non protein compounds Tannins = (leukocytes) ( vitamins, carotenoids, minerals, flavonoids Tannoïdes Phenolic compounds Detoxification Uric acid, GSH, ...) ( microsomes ) Pollution, irradiation Imbalance Tannins : particular class of polyphenols, do association with proteins Oxidative stress Oxidative stress is an unbalanced situation 1

  2. POLYPHENOLS IN THE FOODS Some chemistry (2) ( ref: Guyot and al /inra-France) main combinations (ref/E.Rock:Inra Clermont/France) O structure and functionality O H H O O Hydrophil groups O H H H O H O H Esterification H O H OH O H O H H O O H C O H O H O H O H C C O H O O H O H • Physico-chimistry : solubility, O H O H O H H O O O H interact with polysaccharides, H O O C C O H O H O H O H protéins … O H H O O H O O O O H O H C H O H C H 2 O H Glycosylation O H O O H O H • Biochimistry reactivity:oxydation, H O O O H R etc … O H O H H O H H O O O H O H O H Thousands of molecules in the diet Hydrophob group Polymerisation Main class of polyphenols of interest in fruits Main class of polyphenols ( ref Wikipedia/ internet) Phenols acid simple C O O H C O O H Main class of polyphenols: Phenolic acids C6-C1ou C6-C3 simple polyphénol and phenolic O H O H acid flavonoids Cafeic acid Benzoic acid Gallic acid Vanillic acid coumarins & naphtaquinones tanins Main class of polyphenols Some chemistry (1) ( ref: Guyot and al /inra-France) Phenol group H Basic structure of this OH H C Main class of polyphenols: phenolic compound C C simple polyphénol and phenolic acid C C C H R : can be a sugar, organic acid flavonoids R H coumarins & nathataquinones Ex : Catéchin H H tanins C OH C C H POLY phénols C C H O C O C C C CH OH H C C CH C C H OH H 2 O H 2

  3. Main class of polyphenols of interest in fruits Main class of polyphenols of interest in fruits ( ref Wikipedia/ internet) ( ref Wikipedia/ internet) Flavonoids(anti-oxydants+++) with or no aglycone, heterosides, methoxylation) Coumarins and naphta quinones Flavonols Coumarine aromatic compounds Flavones Isoflavones Flavonoids Flavanones C6-C3-C6 Flavanols Anthocyanids Naphta quinone Flavanone /hetrosides form:: cytotoxic, anti bacterian,.anti fungi, hesperidine, naringine) Flavonol ( rutine) Aglycones: quercetol, kamepferol Quercetol or (Quercetine) (aglycone form) Main class of polyphenols Main class of polyphenols of interest in fruits ( ref Wikipedia/ internet) Flavonoids(anti-oxydants+++) Flavanols , anthocyandols (with or no aglicones, gallates, polymeres, heterosides) Main class of polyphenols: simple polyphénol and phenolic acid flavonoids coumarins & nathataquinones Catéchine heterosid form: epicathechin Anthocyanidol : aglycone form: tanins exemple:pelargonidol, delphinidol or Anthocyanidin: hererosides forms: exemple :anthocyanes cyanidol 3,5 di glucoside Main class of polyphenols of interest in fruits Main class of polyphenols of interest in fruits ( ref Wikipedia/ internet) Tanins… class Acide ellagique Tanins complex: - ellagitanin and epicatechine - condensed tanins : flavonols polymer Gallo tanin 3

  4. IMPORTANT PHYSICAL AND CHEMICAL PROPERTIES OF Basic polyphenols analysis CAROTENOIDS Kimura, M. & Rodriguez-Amaya, D.B. (1999), Brazil; HPLC – UV : individual molecules analysis Quench singlet Scavenge or interact RT: 0.00 - 42.97 SM: 7B RT: 3.00 - 40.00 SM: 7B 18.73 NL: 18.65 NL: 100 3.91E7 100 8.14E6 oxygen with free radicals Base Peak F: 95 Base Peak F: 95 - c ESI Full - Advantages : very wel difrenciation - c ESI Full 90 ms [ 90 Après ms [ 50.00- 50.00- Avant 85 85 2000.00] MS 2000.00] MS OX0_DP04 - - 18.18 OX2-DP04 bteween polyphenolic compounds. 80 IO 4 IO 4 80 75 oxydation 75 oxydation 70 70 65 65 21.07 Relative Abundance 60 Relative Abundance 60 23.95 55 55 - limits: 50 50 16.87 26.19 45 45 40 40 - expensive 35 35 15.35 30 30 15.35 25 25 20 - Need standard molecules ( if exist) 20 14.40 CAROTENOIDS 15 19.75 15 Absorb light Lipophilic 10 27.19 10 28.51 14.49 30.53 - Sample preparation very long 5 5 3.15 12.06 31.99 35.54 39.65 13.17 20.65 24.24 7.83 8.91 0.57 3.28 6.20 8.72 11.00 27.89 29.62 33.55 36.47 37.86 41.89 0 0 5 10 15 20 25 30 35 40 0 5 10 15 20 25 30 35 40 Time (min) Time (min) Chromatogrammes LC-MS « Base peak » Bind to hydrophobic Dosage de Folin-ciocalteu, total Polyphénol Easily isomerized content ( no diference between the Pp class, surfaces And oxidized A.Ascorbic) HPLC analysis …. examples (ref: C Mertz and al, 2007) POSSIBLE PROTECTIVE MECHANISMS AGAINST CHRONIC DISEASES - Extraction acetone/water/ formic acid  Quenching of singlet oxygen - Qualitative (LC/MS) and quantitative analysis of major compounds  Scavenging of peroxyl radicals  ellagitannins and anthocyanins (blackberry)  Modulation of carcinogen metabolism  hydroxycinnamic acids (tree tomato, naranjilla),  Inhibition of cell proliferation anthocyanins and kaempferol glycoside (red tree tomato)  Enhancement of cell differentiation via - Analysis of minor compounds in blackberries retinoids  liq-liq extraction with ethyl acetate  Stimulation of cell-to-cell communication  flavonols ( quercetin and kaempferol glycosides)  Enhancement of the immune reponse  ellagic acid glycosides Ref: Mertz and al, 7th International Food Data Conference. Sao Paulo, Oct.2007 Carotenoids Biology Compound Pro-Vitamin A Chemopreventive Induction Relative status activity of junctional inhibition of (Inhibition of C communication lipid peroxidation proliferation) The carotenoids ….. __________________________________________________________________________________ b -Carotene ++++ ++++ ++++ ++ Main reference in the area: Canthaxanthine - ++++ ++++ +++ Lutein - + +++ +++ Kimura, M. & Rodriguez-Amaya, D.B. (1999), Brazil Lycopene - +(+) ++ +++ Vit E - + + ++++ Retinoic acid ++++ ++ +++ ND Acycloretinoic acid - +(+) + ND Kimura, M. & Rodriguez-Amaya, D.B. (1999), Brazil; 4

  5. PRINCIPAL CAROTENOIDS IN FOODS CAROTENOIDS CONSIDERED IMPORTANT TO HUMAN HEALTH b -Carotene Lycopene OH OH OH b -Cryptoxanthin HO HO Lutein OH OH Lycopene OH OH HO HO Zeaxanthin HO HO Lutein CAROTENOIDS CONSIDERED IMPORTANT TO HUMAN HEALTH The and Antioxydant value b -Carotene And bioavailability approach OH b -Cryptoxanthin Total Carotenoid Total Carotene b -carotene The Antioxydant value Provitamins A Principal Carotenoids (Provitamin and Non-Provitamin A Carotenoids) Cis – and trans - isomers Complete carotenoid composition EVOLUTION OF CAROTENOID ANALYSIS 5

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