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1 KOREAN J. FOOD SCI. TECHNOL. Vol. 40, No. 6, pp. 611~620 (2008) The Korean Society of Food Science and Technology Š w s qp g s qp k e ƒ y e w ½ xá * w w t w Effects of Phosphatidylcholine and Phosphatidylethanolamine from Egg Yolk on Thermal Oxidation of Canola Oil Kanghyun Kim and Eunok Choe* Department of Food and Nutrition, Inha University Abstract The principal objective of this study was to assess the effects of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) extracted from egg yolk on the oxidation of tocopherol-stripped canola oil and its browning, as well as their content changes during 12 hr of heating at 180 o C. PC and/ or PE contents in the oil were measured at 200, 500, 1,000, or 2,000 ppm. PL contents in the oil and oil browning were determined by high performance liquid chromatography (HPLC) and spectrophotometry, respectively. The oil oxidation was evaluated by the combination of fatty acid composition, conjugated dienoic acid content, and p-anisidine value. PC was degraded at a slower rate than PE during heating and the co-presence of PE reduced its rate of degradation. PE increased oil browning more profoundly than PC did. PC significantly reduced oil oxidation during heating; however, we noted a possible antagonism between PE and PC in reducing the oil oxidation. Egg yolk PC was a better antioxidant in oil oxidation during heating. Key words: phosphatidylcholine, phosphatidylethanolamine, canola oil, oxidation, heating œ» w o C ƒ y w, w ƒ y t w v w (1). ƒ y w e, w,, ƒ, y y (1). y y ù» w mgr,, s r w (2). w y y š ù z x ¾ w. y j yw x w ù(3-6), y g e w (7) y w. w ƒ w yw y» w š (8). ù w j, g x sy w y w š (9). *Corresponding author: Eunok Choe, Department of Food and Nutrition, Inha University, Incheon , Korea Tel: Fax: eochoe@inha.ac.kr Received August 7, 2008; revised October 17, 2008; accepted October 21, 2008 ù y w ƒ û y w, ƒ w o½ ww 150 o C š y w w». (10) y w z z z y e w w. w (11) Š ƒw 180 o C w» 25 o o½ o½ t yƒ w š w o½ y Š w w š. Š w phosphatidylcholine(pc) phosphatidylethanolamine(pe) wš e ƒw z 180 o C ƒ w š ƒ y e w y z sƒwš, y wì sƒw o½ š y k w» œwš w. Š CKF t (Yangpyeong, Korea) w, e (refined, bleached, deodorized canola oil) F&B(Seoul, Korea) w., 14% BF 3 - k, t t(pc, PE), t t, ù(activity 611
2 612 w t wz 40 «6y (2008) grade, neutral type WN-3) Sigma-Aldrich (St. Louis, MO, USA), TLC plate (precoated Kieselgel; 60 F ) 254 silica gel 60( mesh ASTM) Merck (Darmstadt, Germany), high performance liquid chromatography(hplc) mù p, k k J. T. Baker (Philipsburg, NJ, USA) w w š, w. Tocopherol-stripped canola oil Tocopherol-stripped canola oil(tsco) e l ù f j m v w (12)., e n-x z ùƒ f (30 mm i.d. 300 mm) wš, x g. z œ»(n-n series, Eyela, Tokyo, Japan) w ú ü TSCO z š j m v (13) w mgr y w., TSCO n-x 0.2 µm polytetrafluoroethylene syringe filter(0.2 µm 13 mm; National Scientific Co., Lawrenceville, GA, USA) w z, 20 µl š j m v(younglin SP 930D, Younglin Instrument, Anyang, Korea) w. µ-porasil column( mm, 10 µm i.d. Waters, Milford, MA, USA) w š, x : v q yw (99.8:0.2, v/v) 2.0 ml/min g. w xÿ» q excitation 294 nm, emission 330 nm. Š l Š w k x w Palacious Wang (14) w w z (Fig. 1), Weining (15) xw e f j m v (silica gel column chromatography, SGCC) w., j s k (2:1, v/v) yw ww e f (30 mm 300 mm) wš w g 30 z. ƒ z z œ» w w z j m v (thin layer chromatography; TLC)(16,17) PC PE y, w z w., ƒ z j s k yw (2:1, v/v) TLC q wš j s, m, k, p, (65:20:10:10:3, v/v/v/v/v) yw w z, 5% y ƒ 110 o C 10 g PC PE t R f w Fr 13-Fr 30 Fr 3-Fr 5 ƒƒ PC PE w w z y w (Fig. 2). z TLC q Fr 13-Fr 30 Fr 3-Fr 5 j s k yw (2:1, v/v) TLCq wš k z PC PE ü š w ú ü PC PE ƒƒ w. PC PE HPLC (18) w PC PE t t retention time w y w (Fig. 3).»» Younglin SP 930D HPLC, f Cosmosil packed column 5SL-II( mm; i.d., 5 µm; Nacalai Tesque, Kyoto, Japan), mù p, k, yw (80:20:0.35, v/v/v) w š, UV» q 205 nm š w. ƒ y e ƒ y w PC PE sƒw» Fig. 1. Scheme for crude phospholipids extraction from egg yolk. Fig. 2. Thin layer chromatogram of crude phospholipid fractions obtained by silica gel column chromatography (1-2, Fr 1-Fr 2; 3-4, Fr 3-Fr 5; 5-6, Fr 6-Fr 12; 7-10, Fr 13-Fr 30; 11, standard PE; 12: standard PC). w Š w PC PE TSCO 0, 200, 500, 2,000 ppm ƒƒ ƒwš 60 C 15 o w. wì Š w PC PE TSCO 1,000 ppm ƒƒ, 1,000 ppm yw ƒwš 60 C o 15 w ƒ e y w PC PE y sƒw w. y w 50 ml 5g š œ» w w z open-capped aluminum cap. ƒ 180 o C oven 12 ƒ w 4
3 » ƒ y w Š w 613 Fig. 3. HPLCs of PC and PE. Éü w. 2z xw w. Š w TSCO Š, w gas chromatography (GC) w w (11).»» Supelcowax 10 capillary column(30 m 0.53 mm 10 µm thick; Bellefonte, PA, USA) y»ƒ Varian CP GC(Varian, Palo Alto, CA, USA),,»,» ƒƒ 240, 280, 280 o C. x 30 ml/min š, split ratio 50:1. t t retention time w w, ƒ ùkü peak area w t w. w» HPLC (18) w w, PC PE t t w š w w. ƒ y ƒ y King (19) w 0.1 g j s 3mL UV-Visible spectrophotometer(hp 8453, Hewlett Packard, Wilmington, DE, USA) w 430 nm Ÿ d w sƒw. y ƒ y GC w y(11) AOCS (20) w œ (conjugated dienoic acid, CDA) (Ti la-64) (p-anisidine value, PAV; Cd 18-90) sƒw. m SAS/PC(version 9.1, SAS Institute, USA, 2003) w (Duncan s multiple range test) z (regression coefficient) w w 5%. s³, t r, xz Microsoft excel 2003(Microsoft Co., Redmond, WA, USA) w. š TSCO Š TSCO (43.9±0.07%), (38.1±0.03%), q p (8.5±0.01%), (5.7±0.07%), l (2.1±0.01%). Š PC (35.7±0.99%), q p (34.9±1.29%), (15.8±0.31%), l (11.6±0.06%), j (1.6±1.55%), PE l (31.1±0.58%), (22.8±0.45%), q p (18.0±0.24%), j (14.5±0.08 %) (13.4±0.13%). PC PE w q p w l j w û PE p sy w PC w. w PC PE š(14,21) w.
4 614 w t wz 40 «6y (2008) Fig. 4. Content changes of PC and PE added to tocopherol-stripped canola oil during heating at 180 o C. Fig. 5. Content changes of PC and PE co-added to tocopherol-stripped canola oil during heating at 180 o C. Š ƒwtsco ƒ y Š PC PE 200, 500, 2,000 ppm ƒ w TSCO 180 o C 4 ƒ w w y Fig. 4. TSCO ƒ w PC PE w ƒ 1-3 z, PEƒ PC. ƒ Š w ùkü û Zamora (22) š. Fig. 5 PC PEƒ 1,000 ppm wì ƒ TSCO ƒ PC PE w. TSCO ƒ PC PE 180 o C 4 ƒ w ƒ w. ù PC w PC PE 1,000 ppm ƒƒ ƒw TSCO PC PE 1,000 ppm wì ƒw TSCO w (p<0.05) û. ù PE w TSCO PC PE ƒƒ ƒw PC PE wì ƒw ƒ. PC TSCO wì ƒ PE w ù, PC PE w w ùkü. Š ƒw TSCO ƒ y Š PC PE 0, 200, 500, 2,000 ppm ƒ w TSCO 180 o C 12 ƒ w 430 nm Ÿ d w TSCO y Fig. 6. TSCO y ƒ ƒw ƒw w. TSCO ƒ y PC ƒ w ƒw w ù, PC ƒ w. ù, w
5 » ƒ y w Š w 615 Fig. 6. Effects of PC and PE on browning of tocopherol-stripped canola oil during heating at 180 o C. PE TSCO ƒw 180 C ƒ w TSCO o y PE ƒ ƒ ƒw w ƒw (p<0.05). g» ƒ PC» ƒ PE ƒ TSCO y wù w yw w» w š ƒ. sy w w wš yw w hydroxyalkylpyrrole yw (23). Zamora PE ƒ w pyrrolized phospholipids yw šw (22). ù PC PE ƒw TSCO ƒ w y ùkü ƒ y TSCO ƒw w» w w w. ƒ y ƒ w w yw w w» w (24-26). TSCO ƒ yƒ» w ƒ 1,000 ppm PC PE, wì TSCO ƒw TSCO y ùkù (Table 1). PC PE wì ƒw ƒ w TSCO PC PE ƒ w y w w û y ùkþ., PC PE ƒƒ 1,000 ppm ƒw 12 ƒ w TSCO y ƒƒ 0.003, w 0.253, PC PE 1,000 ppm wì ƒw 12 ƒ w TSCO y , PC PE ƒƒ ƒw TSCO y w w (PC w y+» w y+pe w y+» w y)ƒ ùkú, PC PE wì ƒw TSCO y (PC z +PE z +» w y) w PC PE wì ƒw ƒ w TSCO yƒ PC PE ƒw TSCO y w û ùkû ƒ. Š ƒƒ TSCO ƒ y e w Š l w PC 0, 200, 500, 2,000 ppm ƒƒ ƒwš 180 o C 12 ƒ w TSCO Table 2. TSCO ƒ ƒw q p, l, w ƒw š, w w, q p P/L q p P/Ln ƒ w. P/L P/Ln ƒ y d w t š (27), ƒ y sy q p w sy y ƒ w P/L, P/Ln ƒw yƒ w š ùkü. PC ƒw TSCO PC ƒw TSCO w yƒ š, P/L P/Ln w (p<0.05) û Table 1. Effect of co-addition of PC and PE on the browning (as absorbance at 430 nm) of tocopherol-stripped canola oil during heating at 180 o C Heating time (hr) Separate addition, 1,000 ppm PC PE Sum 1) Co-addition of PC and PE, 1,000 ppm each ) Values are calculated sum of browning in samples added with either PC or PE separately.
6 616 w t wz 40 «6y (2008) Table 2. Effect of PC on fatty acid composition in tocopherol-stripped canola oil during heating at 180 o C Concentration (ppm) Heating time (hr) Relative content (%) 16:0 18:0 18:1 18:2 18:3 P/L 1) P/Ln 2) ± ± ± ± ± ±0.001 b 1.67±0.18 a ± ± ± ± ± ±0.002 a 2.28±0.05 a ± ± ± ± ± ±0.001 a 4.74±0.95 a ± ± ± ± ± ±0.002 a 7.83±1.48 a ± ± ± ± ± ±0.003 a 1.56±0.02 a ± ± ± ± ± ±0.003 a 2.18±0.02 b ± ± ± ± ± ±0.003 b 3.57±0.02 ab ± ± ± ± ± ±0.001 c 4.91±0.09 b ± ± ± ± ± ±0.002 ab 1.53±0.01 a ± ± ± ± ± ± a 2.32±0.00 a ± ± ± ± ± ±0.005 a 3.89±0.09 ab ± ± ± ± ± ±0.001 b 6.39±0.21 ab ± ± ± ± ± ±0.000 ab 1.51±0.00 a 2, ± ± ± ± ± ±0.003 b 2.06±0.04 c ± ± ± ± ± ±0.004 c 3.30±0.07 b ± ± ± ± ± ±0.015 d 4.70±0.05 b 1) P/L=content ratio of palmitic acid to linoleic acid 2) P/Ln=content ratio of palmitic acid to linolenic acid Table 3. Effect of PE on fatty acid composition of tocopherol-stripped canola oil during heating at 180 o C Concentration (ppm) Heating time (hr) Relative content (%) 16:0 18:0 18:1 18:2 18:3 P/L 1) P/Ln 2) ± ± ± ± ±0.50 a0.22±0.001 ab 1.67±0.18 a ± ± ± ± ± ±0.002 b 2.28±0.05 a ± ± ± ± ± ±0.001 a 4.74±0.95 a ± ± ± ± ± ±0.002 a 7.83±1.48 a ± ± ± ± ± ±0.000 a 1.51±0.02 a ± ± ± ± ± ±0.001 a 2.37±0.02 a ± ± ± ± ±0.09 a0.39±0.000 ab 4.32±0.15 a ± ± ± ± ± ±0.010 b 6.17±1.44 a ± ± ± ± ± ±0.003 b 1.52±0.09 a ± ± ± ± ±0.10 a0.28±0.001 ab 2.30±0.05 a ± ± ± ± ± ±0.001 b 4.01±0.07 a ± ± ± ± ±0.42 a0.52±0.001 ab 7.57±1.81 a 2, ± ± ± ± ± ±0.001 b 1.52±0.09 a ± ± ± ± ± ±0.003 a 2.38±0.01 a ± ± ± ± ±0.07 a0.39±0.001 ab 4.03±0.05 a ± ± ± ± ± ±0.001 c 5.74±1.47 a 1) P/L=content ratio of palmitic acid to linoleic acid 2) P/Ln=content ratio of palmitic acid to linolenic acid ùkü. PE ƒw 180 C ƒ w TSCO o y PC ƒw TSCO w (Table 3). Table 4 PC PEƒ ƒ TSCO ƒ P/L P/Ln. TSCO ƒ P/L P/Ln (r 2 >0.9), tƒ ƒ w yw y w. PC PE ƒw TSCO ƒ TSCO w ƒ P/L P/Ln ƒ (a ) g PC PE ƒ TSCO ƒ y w w. w PCƒ PE w P/L P/Ln ƒ g PCƒ TSCO ƒ y z. PC PE ƒ w (p<0.05). ƒ TSCO CDA Table 5 ƒ ¼ ƒw. œ œ sy ƒ y p, y» y ƒw w 2,4-hexadienes, trans, trans- trans, cis-œ x (28,29). TSCO œ w š 43.8% w wš y œ
7 Table 4. Regression analysis between heating time and P/L or P/ Ln of tocopherol-stripped canola oil added with PC or PE during heating at 180 o C Additives Regression parameters 1) Kinds Concentration (ppm) w ƒ yw ƒw. Š PC 200, 500, 2,000 ppm ƒƒ ƒw TSCO ƒ PC ƒw TSCO û CDA ùkü š, ƒw PC ƒ ƒw CDA w w. PCƒ TSCO ƒ y w ùk ü, g PC w y š(30) ew. PEƒ ƒ TSCO ƒ CDA PE ƒw TSCO w. PEƒ TSCO ƒ œ ƒ g w, PE w 4 ƒ š j w y w œ ƒ» ƒ. Husain (9) methyl linoleate PE 0.1%, 1% ƒw 50 o C w PE sy w w ƒ» y w šw. TSCO ƒ PAV y Fig. 7 ƒw. ƒ ƒ y 1 y w z w 2-alkenal, 2,4-alkadienal w w» w (2). wr ƒ 12 PAVƒ» ƒ y w Š w 617 a b r 2 P/L ratio None P/Ln ratio PC , PE , None PC , PE , ) P/L or P/Ln=a heating time+b, r=correlation coefficient w w w y w w ƒ. w w o½ š (31,32). PC ƒ TSCO w w š ƒ w w ƒw (p<0.05). ù, PE ƒ CDA ƒ TSCO PAV ƒ k w ù w. Š w PC e ƒ y w y w ww ù PE w y z. Š yw ƒƒ TSCO ƒ y e w 1,000 ppm PC PE ƒƒ, wì ƒw z 180 o C 12 ƒ w TSCO y Table 6. PC PE wì ƒw ƒ w TSCO q p, l, PC PE ƒƒ ƒw TSCO w ƒw š w P/Lrhk P/ Lnƒ û. w TSCO ƒ P/L P/Ln ƒ (a ) PC PE ƒw TSCO PC PE w Ì ƒw TSCO û (Table 7). PC PE wì ƒw ƒƒ ƒw w ƒ y w w. PC PE y wì ƒ ùkù ƒ» w ƒ. 1,000 ppm PC PE ƒƒ, wì ƒw z 180 o C 12 ƒ w TSCO CDA Table 8 ƒ ƒw. PC, PE TSCO ƒ CDA g, 1,000 ppm PC PE wì ƒw TSCO ƒƒ 1,000 ppm ƒw TSCO w û CDA. w PC PE y wì ƒ ù kù ƒ» w ƒ. Table 8 w TSCO ƒ œ w PC PE yw ƒ z ƒ PC PE ƒ z w û, PC PE 1,000 ppm yw ƒw TSCO CDA 0.40 PC PEƒ ƒƒ 1,000 ppm ƒ w TSCO CDA 0.13, 0.38 w 0.51 w û. TSCO ƒ œ PC PE antagonism ƒ w. Hidalgo (30) PC PE yw (1:1, w/w) 400 ppm 60 o C ƒw PC PEƒ 200 ppm» g, Table 5. Effects of PC or PE on conjugated dienoic acid contents of tocopherol-stripped canola oil during heating at 180 o C Additives Heating time (hr) Kinds Concentration (ppm) None 00.33±0.00 w1) 1.95±0.01 p 2.77±0.01 h 3.01±0.00 a PC ±0.01 w 1.86±0.01 r 2.64±0.05 k 2.88±0.04 e ±0.02 v 1.92±0.02 q 2.67±0.13 j 2.95±0.03 b 2, ±0.01 v 1.72±0.08 s 2.44±0.04 l 2.92±0.10 c PE ±0.00 u 2.11±0.04 m 2.81±0.01 f 2.74±0.11 i ±0.00 t 2.08±0.01 n 2.81±0.03 f 2.79±0.04 g 2, ±0.01 v 2.04±0.06 o 2.81±0.00 f 2.90±0.02 d 1) Different superscript means significant differences among samples at α=0.05.
8 618 w t wz 40 «6y (2008) Fig. 7. Effects of PC or PE on p-anisidine value of tocopherol-stripped canola oil during heating at 180 o C.» PC PE š šw. 1,000 ppm PC PE ƒƒ, wì ƒw z 180 o C 12 ƒ w TSCO PAV Table 9 ƒ ƒ w. 1,000 ppm PC PE wì ƒw TSCO 1,000 ppm ƒƒ ƒw TSCO PAV ƒw TSCO w û. œ ƒ PC PE yw ƒ w PAV z PC PE ƒ w TSCO ƒ PAV z w û. PC PEƒ TSCO ƒ w antagonist wš w. Š w PC PE, wš mgr w TSCO 0, 200, 500, 2,000 ppm, 1,000 ppm yww ƒw z 180 o C 12 ƒ w w w y TSCO y r š, TSCO ƒ y e w, œ, sƒw. TSCO ƒ ƒ z 2-3 ü š, ƒ PE w ƒ PC w. PC PEƒ Table 6. Effect of PC and PE mixture on fatty acid composition in tocopherol-stripped canola oil during heating at 180 o C Additive Heating time (hr) Relative content (%) 16:0 18:0 18:1 18:2 18:3 P/L 1) P/Ln 2) ± ± ± ± ±0.50 a0.22±0.001 ab 1.67±0.18 a ± ± ± ± ± ±0.002 b 2.28±0.05 a ± ± ± ± ± ±0.001 a 4.74±0.95 a ± ± ± ± ± ±0.002 a 7.83±1.48 a ± ± ± ± ± ±0.001 a 1.51±0.01 a PC 1,000 ppm ± ± ± ± ± ±0.001 b 2.15±0.02 a ± ± ± ± ± ±0.000 b 3.58±0.09 b ± ± ± ± ± ±0.004 b 6.34±1.24 a ± ± ± ± ± ±0.000 b 1.49±0.10 a PE 1,000 ppm ± ± ± ± ± ±0.001 a 2.23±0.03 a ± ± ± ± ± ±0.000 a 4.00±0.01 a ± ± ± ± ± ±0.010 a 7.27±1.15 a ± ± ± ± ± ±0.002 a 1.54±0.07 a PE 1,000 ppm+ PC 1,000 ppm ± ± ± ± ± ±0.002 a 2.18±0.01 a ± ± ± ± ± ±0.003 b 3.49±0.03 b ± ± ± ± ± ±0.002 c 4.94±0.02 a 1) P/L=content ratio of palmitic acid to linoleic acid 2) P/Ln=content ratio of palmitic acid to linolenic acid
9 » ƒ y w Š w 619 Table 7. Regression analysis between heating time and P/L or P/Ln of tocopherol-stripped canola oil containing PC and/or PE at 180 o C Additives Regression parameters 1) a b r 2 2) None P/L ratio PC 1,000 ppm PE 1,000 ppm PC 1,000 ppm+pe 1,000 ppm None P/Ln ratio 1) P/L, P/Ln=a heating time+b 2) r=correlation coefficient PC 1,000 ppm PE 1,000 ppm PC 1,000 ppm+pe 1,000 ppm Table 8. Effects of co-addition of PC and PE on conjugated dienoic acid values of tocopherol-stripped canola oil during heating at 180 o C Heating time (hr) None Separate addition, 1,000 ppm PC PE Calculated sum 1) Co-addition of PC and PE, 1,000 ppm each ± ±0.00 (0.00) 2) 0.34±0.00 (-0.01) (-0.01) 0.38±0.01 (-0.05) ± ±0.01 (0.13) 1.95±0.06 (0.00) -(0.13) 1.92±0.10 (0.03) ± ±0.01 (0.22) 2.72±0.02 (0.05) -(0.27) 2.51±0.01 (0.26) ± ±0.03 (0.13) 2.68±0.14 (0.38) -(0.51) 2.65±0.04 (0.40) 1) Values are calculated sum of difference between CDA values of samples added with either PC or PE and CDA values of samples without PC or PE 2) CDA values of samples without PC nor PE-CDA values of samples added with PC and/ or PE Table 9. Effect of coaddition of PC and PE in p-anisidine value (PAV) of tocopherol-stripped canola oil during heating at 180 o C Heating time (hr) None Separate addition, 1,000 ppm PC PE Calculated sum 1) Co-addition of PC and PE, 1,000 ppm each ± ±0.15 (3.9) 2) 001.4±0.6 (1.4)0 0(5.3) 00.4±0.4 (2.4) ± ±14.6 (137.2) 379.0±0.5 (6.8)0 (144.0) ±2.6 (57.7) ± ±27.4 (40.1) 478.5±0.5 (18.9) (59.0) 455.9±1.0 (41.5) ± ±3.3 (24.9) 451.9±9.0 (17.8) (42.7) 463.8±2.6 (5.9)0 1) Values are calculated sum of difference between PAV of samples added with either PC or PE and PAV of samples without PC nor PE 2) PAV of samples without PC or PE-PAV of samples added with PC and/ or PE wì ƒ TSCO ƒ w PE PC w w. TSCO ƒ ƒw yƒ ƒw š, PC PE y w PEƒ PC j w. ƒ TSCO P/L, P/Ln, œ, ƒw, PC ƒ û ƒ e y w w ù PE j w ùkü, PC PE TSCO ƒ y antagonism. 1. Choe E, Min DB. Chemistry of deep-fat frying oils. J. Food Sci. 72: R77-R86 (2007) 2. Choe E, Min DB. Mechanisms and factors for edible oil oxidation. Compr. Rev. Food Sci. 5: (2006) 3. Sugino H, Ishikawa M, Nitoda T, Koketsu M, Juneja LR, Kim M, Yamamoto T. Antioxidative activity of egg yolk phospholipids. J. Agr. Food Chem. 45: (1997) 4. Pokorny J, Davidek J, Vierecklova M, Ranny M, Sedlacek J. Effect of phophorylated acylglycerols on the oxidative stability of oils. Nahrung 34: (1990) x 5. Zambiazi RC, Przybylski R. Effect of endogenous minor components on the oxidative stability of vegetable oils. Lipid Technol. 10: (1998) 6. Yoon SH, Min DB. Roles of phospholipids in the flavor stability of soybean oil. Korean J. Food Sci. Technol. 19: (1987). 7. Saito H, Ishihara K. Antioxidant activity and active sites of phospholipids as antioxidants. J. Am. Oil Chem. Soc. 74: (1997) 8. Zamora R, Hidalgo FJ. Coordinate contribution of lipid oxidation and maillard reaction to the nonenzymatic food browning. Crit. Rev. Food Sci. 45: (2005) 9. Husain SR, Terao J, Matsushita S. Effect of browning reaction products of phospholipids on autoxidation of methyl linoleate. J. Am. Oil Chem. Soc. 63: (1986) 10. Judde A, Villeneuve P, Rossignol-Castera A, Le Guillou A. Antioxidant effect of soy lecithins on vegetable oil stability and their synergism with tocopherols. J. Am. Oil Chem. Soc. 80: (2003) 11. Kim H, Choe E. Effects of egg yolk powder addition to the flour dough on the lipid oxidation development during frying. LWT- Food Sci. Technol. 41: (2008) 12. Lee J, Kim M, Choe E. Antioxidant activity of lignan compounds extracted from roasted sesame oil on the oxidation of sunflower oil. Food Sci. Biotechnol. 16: (2007)
10 620 w t wz 40 «6y (2008) 13. Lee J, Kim M, Choe E. Study on the changes of tocopherols and lignans and the oxidative properties of roasted sesame oil during manufacturing and storage. Korean J. Food Sci. Technol. 40: (2008) 14. Palacious LE, Wang T. Egg yolk lipid fractionation and lecithin characterization. J. Am. Oil Chem. Soc. 82: (2005) 15. Weining Z, Haibo H, Yuqi F, Shilu D. Separation and purification of phosphatidylcholine and phosphatidylethanolamine from soybean degummed oil residues by using solvent extraction and column chromatography. J. Chromatogr. B 798: (2003) 16. Shin HS, Rhee JY. Comparative studies on the lipid content and neutral lipid composition in nonglutinous and glutinous rice. Korean J. Food Sci. Technol. 18: (1986) 17. Choe E, Lee J, Park K, Lee S. Effects of heat pretreatment on lipid and pigments of freeze-dried spinach. J. Food Sci. 66: (2001) 18. Balazs PE, Schmit PL, Szuhaj BF. High-performance liquid chromatographic separations of soy phospholipids. J. Am. Oil Chem. Soc. 73: (1996) 19. King MF, Boyd LC, Sheldon BW. Antioxidant properties of individual phospholipids in a salmon oil model system. J. Am. Oil Chem. Soc. 69: (1992) 20. AOCS. Official Methods and Recommended Practices of American Oil Chemists Society. 5 th ed. AOCS Press, Champaign, IL, USA (1998) 21. Schneider M. Fractionation and purification of lecithin. pp In: Egg Nutrition and Biotechnology. Sim JS, Nakai S, Guenter W(eds). CABI Publishing, Oxon, UK (1994) 22. Zamora R, Olmo C, Navarro JL, Hidalgo FJ. Contribution of phospholipid pyrrolization to the color reversion produced during deodorization of poorly degummed vegetable oils. J. Agr. Food Chem. 52: (2004) 23. Zamora R, Alaiz M, Hidalgo FJ. Modification of histidine residues by 4,5-epoxy-2-alkenals. Chem. Res. Toxicol. 12: (1999) 24. Xu XQ. A chromametric method for the rapid assessment of deep frying oil quality. J Sci. Food Agr. 83: (2003) 25. Totani N, Kuzume T, Yamaguchi A, Takada M, Moriya M. Amino acids brown oil during frying. J. Oleo. Sci. 55: (2006) 26. Totani N, Yamaguchi A, Takada M, Moriya M. Color deterioration of oil during frying. J. Oleo. Sci. 55: (2006) 27. Kim I, Choe E. Effects of red ginseng extract added to dough on the lipid oxidation of frying oil and fried dough during frying and heating. Food Sci. Biotechnol. 12: (2003) 28. Gray J. Measurement of lipid oxidation: A review. J. Am. Oil Chem. Soc. 55: (1978) 29. Lezerovich A. Derivative UV spectra of lipid conjugated dienes. J. Am. Oil Chem. Soc. 63: (1986) 30. Hidalgo FJ, Nogales F, Zamora R. Changes produced in the antioxidative activity of phospholipids as a consequence of their oxidation. J. Agr. Food Chem. 53: (2005) 31. Lee J, Lee S, Lee H, Park K, Choe E. Spinach (Spinacia oleracea) powder as a natural food-grade antioxidant in deep-fat-fried products. J. Agr. Food Chem. 50: (2002) 32. Lee J, Kim M, Park K, Choe E. Lipid oxidation and carotenoid content in frying oil and fried dough containing carrot powder. J. Food Sci. 6: (2003)
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