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Presentación De Powerpoint 6/8/2015 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods FA1104 Training School Qualitative, physicochemical and phytochemical indicators of cherry fruit quality [2-4 June 2015] Extraction of phytochemical components Francisco Tomás Barberán CEBAS – CSIC, Murcia, Spain [email protected] FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Bioactive constituents in cherry Acid/base behaviour and solubility in water melatonin Balaton & Montmorency 1-6 ng/g f.w. HPLC ECD Burkhadt et al., JAFC 2011, 49, 4898. 0,220-0,006 ng/g f.w. HPLC-MS Acid. Water soluble in alkaline conditions Huang & Mazza, Crit. Rev. Food Sci. Nut. 2011, 51, 269 serotonin 0,40-0,03 ng/g f.w. HPLC-MS Huang & Mazza, Crit. Rev. Food Sci. Nut. 2011, 51, 269 Neutral. Water insoluble. Extraction: acid extraction in water and then change to alkaline conditions (KOH) and extract with organic solvent (CHCl3) liquid/liquid extraction Basic. Water soluble in acid conditions FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Oligomeric polyphenols (tannins) Monomeric and oligomeric phenolics in cherries 1 6/8/2015 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Extractable/Non-extractable polyphenols Extraction methods (extractable) • Polyphenols Extractable phenolics – Problems: stability (anthocyanins); oxidation by oxygen, by PPO (enzymatic); precipitation. • Fresh plant material. – (Methanol 80 °C). Problem with anthocyanins. – Methanol-Water (8:2; v:v) + 4 mM FNa + acid (0.1-1%)(HCl, formic acid) (room temp.) (ultraturrax). • Dried plant material (freeze dried) Non-extractable phenolics – Methanol-Water (7:3; v:v) FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Drupe extractable λ = 320 nm Solid Phase Extraction Cartridges 0,14 1 phenolic compounds 16 0,12 5 0,10 Plant extract 98% phenolics 0,08 recovered 0,06 17 0,04 4 20 0,02 3 * 19 6 14 C18 Sep Pack column 0,00 -0,02 0 10 20 30 40 50 HPLC analysis 0.45 mm filtration 0,25 λ = 510 nm 12 0,20 10 0,15 • Cartridge activation with methanol • Removal of methanol with water (and air?) 0,10 • Introduction of sample (solvent, acid addition) 15 • Elution of sample to be analysed (methanol-water mixtures). 0,05 0,00 0 10 20 30 40 50 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Polyphenol Analysis. Extractable/Non-extractable Phenolics (proanthocyanidins) Non-extractable phenolics have been generally overlooked in food composition analysis and databases Extractable Food % extractable % non-extractable Apples and berries 90-100 0-10 Grape 50 50 Pear 50 50 Cranberry 50 50 Red currant 50 50 Kiwi fruit 20 80 Banana 0 100 Tarascou et al., Arch. Biochem. Biophys. 2010, 501, 16 Non-extractable Food % extractable % non-extractable Apple 10 90 BuOH/H+ Peach 15 85 Nectarine 5 95 Arranz et al., J. Agric. Food Chem., 2009, 57, 7298. 2 6/8/2015 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Gallotannins Kennedy & Jones, 2001, JAFC Galloyl Extension hexahydroxydiphenoyl unit Gallic acid m/z 169 Extension Drupe NON-extractable Ellagic acid m/z 301 unit phenolic compounds Terminal unit Valoneic acid dilactone m/z 469 Mean degree of polymerization Punicalagin m/z 1083 Other ellagitannins Sanguiin H-10 type Sanguisorbic acid dilactone m/z 469 Analysis of non-extractable m/z 463 epicatechin-adduct proanthocyanidins Gallagic acid dilactone m/z 601 by phloroglucinolysis catechin Catequin adduct Punicalin m/z 781 C-glycosyl ellagitannins epicatechin m/z 631 Castalagin type ACID HYDROLYSIS PRODUCTS FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Extraction protocol Chromatographic method Stationary phase: C18 column 1. Place 50 mg of pomegranate extract in a 10 mL pyrex tube (Merck, Darmstadt, Germany) (250 300 1000 (16x100 mm 10 mL) 1200 Supernatant Pellet mm x 4,6 mm, 5 µm particle size) 1200 300 1000 280nm 6 2 6 258 1 2 256 3 A) 250 5 300 270 800 800 1000 250 2. Add 5 mL of 4 M hydrochloric acid, [prepared by adding 3.33 mL 600 800 200 200 Abs, (mAU) Abs, 400 200 600 150 of water and 1.66 mL of concentrated commercial 37% hydrochloric Mobile phase: water with 1% formic 200 Abs (mAU) Abs 100 Abs (mAU) Abs 600 100 380 400 (mAU) Abs 374 acid. Vortex 1 min acid (A) and acetonitrile (B) 0 200 50 0 2 4 6 8 10 150 Time (min) 0 0 0 Gradient: 400 4 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 3. Hydrolyze in an oven at 90ºC for 24 h 100 m m m 400 600 1200 de 0 a 20 min, 5% B a 30% B 4 256 5 6 256 256 8 500 1000 4 Abs, 360 nm (mAU) Abs, 360 nm (mAU) nm Abs, 360 3 200 300 de 20 a 30 min, 30% de B a 55% de B 50 400 4. Leave tubes cool at room temperature 1 800 8 9 11 8 8 11 200 300 600 de 30 a 38 min, 55% de B a 90% de B 8 8 10 3 910 200 380 (mAU) Abs 0 (mAU) Abs (mAU) Abs 400 0 100 366 372 5. Transfer the content of Pyrex tube to a 15 mL falcon tube and de 40 a 48 min, 90% de B a 5% de B 100 200 0 adjust the pH at 2.5 M with 10 M and 5 M NaOH 0 5 10 15 20 25 0 5 10 15 20 25 0 0 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 Flow: 1 ml/min Time (min) Time (min) m m m 300 35 40 80 8 258 9 10 6. Centrifuge the falcon for 10 minutes at 3500 x g. 250 256 30 258 25 30 Supernatant +pellet 200 Injection volumen: 10µl 5 6 20 150 20 15 7. Recover the supernatant and adjust the volume to 10 mL with 100 374 378 UV spectrum: 280 and 360 nm 10 332 Abs (mAU) Abs Abs (mAU) Abs 60 (mAU) Abs B) 372 10 400 50 5 water in a 10 mL measuring cylinder 0 0 0 -50 -5 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 8. Filter the supernatant through a 0.45 µm PVDF filter and inject in Hydrolysis of punicalagin standard 40 m m m 18 16 256 11 HPLC-UV. 50 14 12 10 20 8 Abs, 360 nm (mAU) 6 9. Dissolve the pellet with 10 mL dimethyl sulfoxide:methanol (50:50 40 368 8 (mAU) Abs 4 8 2 9 v/v) by vortexing (2 min) and filter through a 0.45 µm PVDF filter. 0 -2 30 0 -4 Dilute the sample 1:10 with dimethyl sulfoxide:methanol (50:50 v/v) 250 300 350 400 450 acid Ellagic m before injecting in HPLC-UV. acid Gallagic 5 10 15 20 25 Time (min) 20 1200 300 1 300 258 270 2 256 3 1000 250 (360 nm), mAUAbs C) 10 800 200 200 600 150 0 380 400 100 Abs (mAU) Abs 100 Abs (mAU) Abs (mAU) Abs 374 200 50 0 5 10 15 20 25 30 0 0 ACID HYDROLYSIS PRODUCTS OPTIMIZED METHOD Time (min) 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 m m 400 m 600 1200 6 256 4 5 256 500 256 1000 300 400 800 200 300 600 380 200 400 Abs (mAU) Abs Abs (mAU) Abs 366 (mAU) Abs 100 372 100 200 0 0 0 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 m m m 300 35 40 8 258 9 10 250 256 30 258 25 30 200 20 150 20 15 374 100 332 378 10 400 372 (mAU) Abs Abs (mAU) Abs 10 Abs (mAU) Abs 50 5 0 0 0 -50 -5 250 300 350 400 450 250 300 350 400 450 250 300 350 400 450 m m m 18 16 256 11 14 12 10 8 6 FA1104 Training School FA1104 Training School 4 368 Abs (mAU) Abs 2 0 Determination of phytochemical components with advanced Determination of phytochemical components with advanced -2 -4 250 300 350 400 450 analytical methods analytical methods m Proanthocyanidin microbiota metabolism 8 7 Drupe proanthocyanidins 6 5 4 3 2 Extractable 1 microbiota 0 non-extractable extractable Non-extractable microbiota Depolymerization ? Are non-extractable phenolics relevant? Touriño et al., JAFC, 2011, 59, 5955 3 6/8/2015 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Microbiota conversion of non-extractable proanthocyanidins Fruit & Vegetable bioactives and human health Mean degree polymerization Tarascou et al., ABB, 2010 ; Bazzoco et al., Eur. J. Nut, 2008 FA1104 Training School FA1104 Training School Determination of phytochemical components with advanced Determination of phytochemical components with advanced analytical methods analytical methods Evaluation of Bioactives Antioxidant evaluation in vitro • Does not consider bioavailability and metabolism • Antioxidant capacity evaluation of food constituents – ABTS, FRAC, TEAC, DPPH, ORAC, etc.
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