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11. COMPOUNDS INFLUENCING FOOD COLOUR Perception Visual 11. COMPOUNDS INFLUENCING FOOD COLOUR perception visual colour pigments (colouring matters, colourings) formation primary compounds natural food components natural components of other materials (microorganisms, algae, higher plants), used as additives secondary compounds enzymatic reactions (non-enzymatic browning reaction) chemical reactions synthetic compounds used as additives colour defects natural colours important groups tetrapyrrole colours plants, animals hem colours chlorophyll colours betalain colours plants betacyans betaxanthins flavonoid colours plants anthocyanins anthoxanthins phenolic and quinoid colours plants, animals phenols quinones carotenoid colours plants, animals carotenes xanthophylls TETRAPYRROLE PIGMENTS (TETRAPYRROLES) porphyrin pigments (porphyrins) cyclic hem pigments (hems) chlorophyll pigments (chlorophylls) biline pigments (bilines) linear phycobilins 3 5 7 4 6 2 A B 8 2 3 7 8 1 NH N 9 12 13 17 18 20 10 4 6 9 11 1 A B C 14 16 D 19 19 NH 11 N N N 5 10 N 15 N 18 D C 12 H 16 14 17 15 13 porphyrins bilines hem pigments meat, meat products nomenclature (book 3, tab. 9.1) content (book 3, tab. 9.2, 9.3, 9.4, 9.5) P CH2 N H His93 CH2=CH CH3 N CH2=CH CH3 H C CH=CH 3 2 H C CH=CH N N 3 2 N N Fe (II) Fe (II) N N N N H3C CH3 H3C CH3 CH CH COOH HOOCCH CH HOOCCH2CH2 2 2 2 2 CH CH COOH H2O 2 2 hem (reduced haematin, Fe2+), hemoglobin hematin (Fe3+), myoglobin (P = globin residue,16,8 kDa) protein protein N N O 2 N N myoglobin Fe (II) Fe (II) oxymyoglobin N N N N O O H2O protein N N metmyoglobin Fe (III) N N OH myoglobin (Mb) dark red oxymyoglobin (MbO2) scarlet metmyoglobin (MMb) red to brown reaction of MMb during temperature processing of meat metmyoglobin globin denaturation (70-80oC) globin hydrolysis hematin or hem (loss of Fe3+ or Fe2+) linear tetrapyrroles stabilisation of meat and meat products colour microorganisms in meat: NO3- NO2- - spontaneous reaction: 2 Mb + NO2 2 MMb + NO + H2O 2 Mb + NO MbNO + H2O heating: MbNO Mb(NO)2 + globin MbNO = nitroxymyoglobin Mb(NO)2 = nitroxyhemochrom (nitrosylhemochrom, nitroxymyochromogen) use of ascorbic acid: MMb + H2A Mb + A fuscous up to green colours (sulphomyoglobin, verdochrom, cholemyoglobin) chlorophyll pigments green parts of fruits and vegetables content (book 3, tab.9.7) colour (book 3, tab.9.8) CH2=CH R H3C CH2CH3 N N N N Mg (II) Mg (II) N N N N H3C CH3 CH2 O C O CH2 O C O CH3 methyl fytyl O CH3 CH3 CH3 CH3 CH 3 porphyrins chlorophylls Mg (II) complex chlorophylls R = CH3 chlorophyll a yellow-green R = CH=O chlorophyll b blue-green without Mg (II) pheophytin without phytol chlorophyllide without Mg (II) and phytol pheophorbide reactions of chlorophylls during processing (acids, enzymes) chlorofyly slabá kyselina chlorofylasa feofytiny silná kyselina chlorofylidy silná kyselina silná kyselina feoforbidy colour changes during processing (book 3, tab. 9.9, 9.10 ) colour stabilisation 3 + 2 H N N 2+ - Mg NH N chlorofyl Mg (II) feofytin + N N - 2 H N HN 2+ Mg 2+ 2+ 2+ + Cu , - Mg Cu , - 2H N N Cu (II) měďnatý komplex N N o chlorophylin Cu (chlorophylid Cu) betalain pigments beetroot, prickly pear, amaranth, flowers betacyanins red, orange betaxanthins yellow, orange basic structure 1 R + R N H HOOC N COOH H CH2OR R O O OH O H H + HO + - OH HO N COOH N COO H H N COOH HOOC N COOH HOOC H H betanin (R = H) 95 % vulgaxanthin I (R = NH2) 50 % flavonoid pigments fruits, vegetables, flowers anthocyanins red, violet, blue anthoxanthins yellow, orange basic structure 4 O O A B C 2H-chromene flavan oxidation of 3C chain (ring B) OH groups in rings A, B, C aglycones, glycosides O O O O OH OH OH OH OH O O katechiny leukoanthokyanidiny flavanonoly flavonoly O O O O flavanony flavony O + anthokyanidiny colourless colourless-light pale yellow light yellow-yellow red-blue O O isoflavony light yellow OH OH O O O O chalcones dihydrochalcones aurones yellow-orange yellow-orange gold-yellow anthocyanins basic structure 5 R1 OH HO O 2 + R 7 3 5 OH OH pelargonidin Pg R1 = H R2 = H violet-red cyanidin Cy R1 = H R2 = OH violet delfinidin Dp R1 = OH R2 = OH blue-violet 1 2 peonidin Pn R = H R = OCH3 violet 1 2 petunidin Pt R = OH R = OCH3 dark red 1 2 malvidin Mv R = OCH3 R = OCH3 blue-violet saccharides: Glu, Gal, Xyl, Ara, Rha, always at C-3, often at C-3 and C-5, seldom at C-7 acids: p-cumaric, caffeic, ferulic O H O H HO O + O HO HO CH2 O HO O H O H examples cyanidin-3-O--D-glucoside (general occurrence) OCH3 OH petunidin HO O CH3 + OH O 3 OH HO OH OH 5 O O O CH OH 2 O OH C O H2C O O D-glukosa OH OH p-kumarová kyselina HO rutinosa OH petanine (red coloured potato) (E)-petunidin-3-O-6-O-(4-O-p-cumaroyl--L-rhamnopyranosyl)--D-glucopyranoside-5-O--D- glucopyranoside anthocyanins fruits and vegetables (book 3,. tab. 9.12) colour changes due to different factors pH co-pigmentation, eventual transformation into other pigments SO2 H2O2 6 pH 1 1 R R OH OH OH HO O HO O + 2 2 H2O,- H R + R O glykosyl O glykosyl O glykosyl O glykosyl pH < 1 pH 4,0-4,5 flavyliový kation (červený) karbinolová pseudobáze (bezb.) + - H + 1 1 - H2O - H R R O OH HO O 2 O O 2 R R R1 OH O glykosyl O glykosyl OH O glykosyl O glykosyl HO 2 pH 4,5-7,5 O R neutrální chinoidní báze (tmavě červená) O glykosyl + glykosyl - + - H O pH > 8 H 1 1 R R - O chalkon (žlutá) O - O O 2 O O R R2 O glykosyl O glykosyl O glykosyl O glykosyl pH 7,5-8 anion chinoidní báze (modrá) copigmentation interaction with procyanidinins (catechins = copigments) coloured complexes transformation into other pigments, coloured complexes dimers (oligomers), non-soluble condensation products, polymeric compounds R OH anthokyanidin HO O + R 4 R OR OH OR HO O 8 R katechin OH OH SO2 colourless sulfonic acids R1 R1 OH OH HO2SO HO O 2 O R R 2 O glykosyl O glykosyl O glykosyl glykosyl O OSO2H H2O2 colourless products R1 OH O R2 C HO O O O glykosyl O glykosyl 7 anthoxanthins flavanones pigments of low importance bitter compounds of grapefruits naringin = naringenin + neohesperidose neohesperidin = hesperetin + neohesperidose flavanonols pigments of low importance flavones important anthoxanthins flavonols important anthoxanthins antioxidant activity, rutin = kvercetin + rutinose, bioflavonoids isoflavones pigments of low importance (e.g. in soybeans) estrogenic activity chalcones and aurones important pigments of flowers dihydrochalcones pigments of low importance neohesperidindihydrochalcone (synthetic sweet compound) quinoid pigments lichens, mushrooms, higher plants phenols quinones phenols curcuminoides (diarylheptanoides) O O CH3O OCH3 HO OH curcumin (curcuma, curry) quinones benzoquinones naphtoquinones anthraquinones O O O O O O benzo-1,4-quinone naphto-1,4-quinone anthra-9,10-quinone 8 benzoquinones OH HOCH2 O O OH HO OH arbutin (cranberry leaves, antiseptic activity) (related terphenylquinones and pulvic acids in mushrooms) naftoquinones O OH O juglone (leaves of walnut, 4--D-glucosid 1,4,5-trihydroxynaphtalene) (relative gossypol in cotton seeds, related coenzymes Q, vitamins K) anthraquinones related emodins, bianthrons HO O OH OH O HO OH HO CH CH2OH 3 HO CH O COOH 3 OH OH O CH3 HO OH HO O OH carminic acid (cochineal, dried bodies of female beatles Coccus cacti) hypericine (St. John's wort) carotenoid pigments yellow, orange, red up to violet pigments of plants and microorganisms (in mammals) composition and content in fruits and vegetables (book 3, tab.9.14) carotenoids (tetraterpenes, 40 C atoms, trans-isomers) hydrocarbons carotenes O-derivatives xanthophylls neocarotenoids (cis-isomers) degradated carotenoids (30, 20, 15, 13, 10 C atoms) carotenes acyclic and alicyclic hydrocarbons CH3 CH3 CH3 CH3 CH3 H3C lykopen CH3 CH3 CH3 CH3 H3C OH CH3 CH3 H3C CH3 H3C CH3 CH3 CH3 CH3 -karoten lycopene: tomato, rose-hip, -carotene: carrot, apricot, mango 9 xanthophylls alcohols, ketones, epoxides free, bound (glycosides, fatty acids esters, carotenoproteins) H3C OH CH3 CH3 H3C CH3 H3C CH3 CH3 CH3 HO CH3 zeaxanthin H3C OH CH3 CH3 H3C CH3 H3C CH3 CH3 CH3 HO CH3 lutein (-xanthofyl, kukurbitaxanthin) OH CH3 CH3 H3C CH3 H3C CH3 CH3 O CH3 CH3 HO CH3 kapsanthin O H3C OH CH3 CH3 H3C CH3 H3C CH3 CH3 CH3 HO CH3 O astaxanthin zeaxanthin, lutein: generally wide-spread kapsanthin: red bell pepper astaxanthin: fish, shellfish (-crustacyanin) retinoids degradated carotenoids crocin (18 C) saffron (Crocus sativus), spice CH3 CH3 COOH HOOC CH CH krocetin 3 3 genciobiosa O OH HOCH2 OH CH2OH CH3 CH3 O HO O O CH O 2 C O O OH OH O C OH CH2 HO OH O CH3 CH3 O OH HO OH OH krocin annato (20 C) bixin (Bixa orellana) extract 0,2-0,5 % = mixture cis/trans-isomers, cheese and margarine colouring 10 CH3 CH3 CH3 HOOC 9 , CH3 COOH CH3 CH3 COOH HOOC CH CH3 3 aromatic and gustatory compounds formed from carotenoids H3C CH3 CH O CH2OH O O CH3 OH HO OH pikrokrocin O O oxidace a štěpení H3C CH3 H3C CH3 CH CH3 -karoten 3 + CH3 CH3 -jonon -jonon H3C CH3 H3C CH3 CH O O CH3 O CH3 -cyklocitral dihydroaktindiolid H3C CH3 O O H3C CH3 H C CH 3 3 CH3 CH3 CH3 -damaskon -iron reactions hydrolysis of esters, glycosides dehydration of alcohols to hydrocarbons cis/trans isomeration (neocarotenoids, low colour intensity) autooxidation (low colour intensity, even decolourisation) antioxidants consequences flour bleaching colour changes of orange juices food flavour beneficial food components 11 Enzymatic browning reactions substrates (book 3, tab.
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