Chemical changes of lipid oxidation compounds under simulated gastric conditions
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1 Chemical changes of lipid oxidation compounds under simulated gastric conditions G. Márquez-Ruiz Ruiz,, J. Velasco, A. Morales, F. Holgado & MC Dobarganes Instituto del Frío (CSIC), Madrid & (CSIC), Sevilla SPAIN 1
2 Gastric conditions: Chemical changes of dietary oxidized lipids are largely unknown. Structural changes? Further oxidation? 2
3 Objective: Evaluation of chemical changes of dietary lipid oxidation compounds under in vitro gastric conditions. Experimental conditions: Samples representative of major dietary oxidized compounds: Model oxidized fatty acid methyl esters and oxidized oils Simulated gastric fluid: 3.2% w/v pepsin, 0.03 M NaCl, 0.1 M HCl (ph 1.0) Digestion at 37ºC for 3 h Analytical determinations: - Loss of oxidized compounds by GC-FID/MS - Hydroperoxides and their products by HPLC-UV - Nonvolatile oxidation compounds by CC and HPSEC-RI 3
4 Model fatty acid methyl esters Methyl 12-hydroxystearate OH COOMe Methyl 12-oxostearate O COOMe Methyl 9,10-epoxystearate O COOMe Epoxy-, oxo- and hydroxy- compounds are abundantly formed during frying and baking 4
5 Model fatty acid methyl esters Methyl linoleate hydroperoxides R OOH R OOH 9-OOH 13-OOH Hydroperoxides are major compounds formed during storage 5
6 Quantitative analysis of methyl 9,10-epoxystearate, 12- oxostearate and 12-hydroxystearate by GC-FID/MS 6
7 Digestion of mixture of methyl 9,10-epoxystearate, 12-oxostearate and 12-hydroxystearate by GC-FID/MS [Compounds Mixture] 12 mg/ml 24 mg/ml 48 mg/ml Compounds Epoxy Oxo Hidroxy Epoxy Oxo Hidroxy Epoxy Oxo Hidroxy Loss after digestion (%) 52.7 nd nd 44.4 nd nd 40.3 nd nd 7
8 Monoepoxides HOOC 9 O 10 cis-9,10-es C18:1 O HOOC trans-9,10-es HOOC 9 O 10 cis-9,10-eo C18:2 HOOC HOOC O 12 O 13 trans-9,10-eo cis-12,13-eo O HOOC trans-12,13-eo Quantities in dietary used frying oils: % in oils at the limit of rejection. Velasco et al., J. Agric. Food Chem. (2004) 8
9 Before digestion After digestion O COOMe Methyl 9,10-epoxystearate OH COOMe OH Methyl 9,10-dihydroxystearate 9
10 Digestion of 9,10 epoxystearate Solution A B Volume / Amount 1 ml / 3.4 mg 2 ml / 6.8 mg 3 ml / 10.2 mg 1 ml / 16.7 mg 2 ml / 33.5 mg 4 ml / 67.0 mg Loss after digestion (%)
11 Hydroperoxides: Analytical approach by GC C18:0 A : Original hydroperoxides after reduction C21:0 (IS) hydroxy C18:0 keto C18:0 B : Hydroperoxides after digestion and reduction
12 Digestion of hydroperoxides Solution A B ph Minimum loss after digestion (%)
13 Hydroperoxides: Analytical approach by HPLC-UV ROOH A keto ROOH hydroxy B Time (min) 13
14 Hydroperoxides: Analysis of volatiles after digestion , hexanal; 2, methyl heptanoate; 3, methyl octanoate; 4 and 5, decadienals; 6, methyl 8-hydroxyoctanoate; 7, methyl 8-oxooctanoate; 8, methyl 9-oxononanoate. 14
15 Assays with sunflower oil samples Oils were oxidized at 40ºC Sample concentration for in vitro digestion: 10 mg/ml Analytical determinations: - Peroxide value - Nonvolatile oxidation compounds:oxidized triacylglycerol monomers, dimers and polymers 15
16 Changes in peroxide values of sunflower oils 1600 Initial Peroxide Value (meq 0 2 /Kg) Digested A B C D E F G H Non oxidized 16
17 Sunflower oils: Analytical approach Light petroleum:diethyl ether 90:10 OIL Diethyl ether UNOXIDIZED TRIACYLGLYCEROLS POLAR COMPOUNDS HPSEC TG Dimers Oxidized TG monomers R oxtgm R = Oxygenated function TGD TG Polymers TGP O Dobarganes et al., Pure Appl. Chem. (2000) 17 Ruiz
18 Overall change in nonvolatile oxidation compounds Oxidized sunflower oils (Initial total oxidation, %) C (4.7) D (11.1) E (15.2) F (29.4) G (49.3) H (70.4) Compounds oxtgm TGD +TGP oxtgm TGD +TGP oxtgm TGD +TGP oxtgm TGD +TGP oxtgm TGD +TGP oxtgm TGD +TGP After digestion (%) oxtgm:oxidized triacylglycerol monomers TGD: triacylglycerol dimers TGP: triacylglycerol polymers 18
19 Main results Model compounds: instability of hydroperoxide and epoxide structures while oxo- and hydroxystearate remained unaltered. Changes in epoxystearate: Losses between 15 and 52%. The major new compounds formed were diols. Changes in hydroperoxides: Losses between 40 and 70%. New compounds formed include hydroxydienes, ketodienes and volatiles. Sunflower oils: changes only in oxidized oils. - General increase of total oxidation compounds. - Decrease of peroxide value in highly oxidized oils. - Polymer formation in highly oxidized oils. 19
20 G. Márquez-Ruiz Ruiz,, J. Velasco, A. Morales, F. Holgado & MC Dobarganes Instituto del Frío (SPAIN) 20
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