Optimization for the Production of Mono- and Di-acylglycerols from Corn Oil by Enzymic Glycerolysis Using Response Surface Methodology

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(1)KOREAN J. FOOD SCI. TECHNOL. Vol. 36, No. 5, pp. 717~722 (2004). ©The Korean Society of Food Science and Technology. >wRª+ö ~ K>>F F¾ monoacylglycerol diacylglycerol 9 ~ R'z ;¾ÁRçö1Á8* ÏÎv ®", 1ÎÓv ®'·". Optimization for the Production of Mono- and Di-acylglycerols from Corn Oil by Enzymic Glycerolysis Using Response Surface Methodology Rae-Kyun Park, Sang-Won Choi1, and Ki-Teak Lee* Department of Food Science and Technology, Chungnam National University, 1 Department of Food Science and Nutrition, Catholic University of Daegu Response surface methodology was used to optimize production conditions of monoacylglycerol (MAG) and diacylglycerols (DAG) from corn oil by enzymic glycerolysis. Contents of 1,3-DAG (Y1), 1,2-DAG (Y2), total DAG (Y3), MAG (Y4), and total DAG + MAG (Y5) were obtained. Conditions were optimized using central composite design with incubation temperature (35-75oC, X1), incubation time (1-11 hr, X2), and amount of hexane added (0-2 mL, X3) as three variables. Content of 1,3-DAG was maximized by 20.43 area% at incubation temperature of 44.92oC, incubation time of 10.24 hr, and hexane content of 1.16 mL, whereas that of 1,2-DAG (26.78 area%) was maximized at 56.32oC, 6.95 hr, and 1.04 mL, respectively. Predicted maximum total DAG content was 45.09 area% at 53.82oC, 8.03 hr, and 1.08 mL, while production conditions of MAG (9.57 arae%) were 64.14oC, 7.00 hr, and 0.13 mL. At variables of 54.07oC, 7.98 hr, and 1.02 mL, maximum content of total DAG + MAG predicted by RSM was 53.54 area%. Key words: RSM, diacylglycerol, monoacylglycerol, glycerolysis. *. . Ú W, æï 5 ¢ Úº 6j æî² > W " ; 7 ôf ö.æ& ²j>º ^B6j æò (6,7). > " &v> ®º Î²' >wö ~ DAG, MAG W O» f *~, Vî 5 ßW Î² j Ï~ W~¶ ~º FÏ bîj ÎN'b Ö > ®b, $ z' O» Ôf NêöB jv' ¸f >N~ Öbj áj > ®Ú ;B jÏ 5 ö.æ ²j¢ *¢ > ®º 6j &ê. (7,8). Þ *~ Î²' glycerolysis >wj Ï DAG F Fæ¢ W~º O» öº çêöB~ >w" W "; 7 &> >wÊº O» ²B>îb(1,5-7), Park(9) f Pseudomonas lipase¢ ÒÏ Î²' glycerolysis >wj Û~ 72* ê 47% DAG¢ Ö~& . >wªC(Response surface methodology, RSM)f B ~ ëãæ>& ~¾~ «³æ> $º ÚÊ >wö 'Ëj * r ' >& öïj Ï'b ~º Ûê V»b æ> ç^~Wj æîº ãÖöê 'Ï &Ë~ þ >¢ 6 ²Êº 6j æò (10,11). >wªCj Ï~ ®BB B 'z 5 ºÂ 'z ª ¢ö wÏ &Ë~ (12,13). $ >wVî ÒÏB K>> Fº &vFf jv~ FÒ æOÖ W" Özn;W ¸f ßûj æî ®b¾(14,15), Fæ Öë 7 &;Ï Ë öB 70% ç~ Wj¢ Næ~º &vFö j K>>F. " ®ÖëöB diacylglycerol(DAG) 5 monoacylglycerol(MAG)º êWB Ï>Ú zb¾(1) " DAG F ® 5 Fæ S Ú7 5 ÚæOj 6² Î º ö ~~ DAG¢ F~º & ¢Ò Fæö & & Ã&> ® (2). DAG F Fæ(" 1,3-DAG ;)º 7W Fæf jv~ ÚÚöB .7 æO ~¢ ¸æ p, &¦ ª &Ë>V º ö.æöb ÒÏ>Ú ÚæO 5 Ú7j 6²Î rJ^ ® (2,3). *Ò Ö 6>º & ¢Ò Fæº &¦ª z' W O»b Ö> ®b, ¢>' b DAGf MAGº 220oC ç~ ¸f >wNêf / $ º Z/ öB &Ò^" ÏFæ~ z' öÊr v~>wö ~ ÖB (1,4,5). ¾, z' W O»ö ~ ÖB « Öbf N~ >w";" >Nj ¸ V * ®~ ª¶Ã~"; 7ö ®z æOÖ~ 7 *Corresponding author: Ki-Teak Lee, Department of Food Science and Technology, Chungnam National University, Gung-dong 220, Yusung-gu, Daejon 305-764, Korea Tel: 82-42-821-6729 Fax: 82-42-822-6729 E-mail: [email protected] 717.

(2) ®"²æ B 36 ² B 5 ^ (2004). 718. ö V ''~ 16&æ J; öB 2² > æîj W ~& .. ~ Wjº 23%¢ ¾æÞ (16). ö Ë6FN Ôf K >>F¢ ÒÏ~ ¦&&~¢ &æº FæÖO»ö & & jº~ ÒòB . V¢B öBº Rhizomucor miehei¦V F¾ lipase ¢ macroporous anion exchange resinö ;zÎ sn-1" 3~ *~ ßWj &ê çëÏ lipase(Lipozyme RM IM)¢ >w/. ÒÏ~ &Ò^" K>>F¢ >wVî ~ *~ W öB glycerolysis >wj Û~ DAG F æ îj W~ 7Wê³(17)ö ~ þJê 5 >w ªCj ÒÏ~ DAG, MAG W 'z ¢ >¯~ & .. DAG 5 MAG ï /; WB æî 7 DAG 5 MAG ïj ªC~V * B áÚê >wÖbö hexane 2 mLj b~ C ê PTFE syringe filter(25 mm, 0.2 µm, Whatman, USA)ö Û"Î r 2,500 rpmöB 15ª ÿn öªÒ~ áÚê çj ~ & . * ¾ÒB æî 50 µLj hexane 10 mLö C PTFE syringe filter(25 mm, 0.2 µm, Whatman, USA)¢ Ï~ "Î ê HPLC(Younglin Acme, Anyang, Korea)ö 10 µL "«~ ªC~& . r HPLC b columnf Hypersil BDS CPS 5 µ(250Ü4.6 mm, Thermo Hypersil Ltd., Cheshire, UK)j ÒÏ~& ¦ÂVº evaporative light scattering detector(ELSD, SEDEX Model 75, France)¢ ÒÏ~&b ¦ÂV~ ªC (19)f î²~ F³ 2.2 bar, Nêº 40oC î . ªCö ÒÏB Ï º '' 0.4% acetic acid¢ hexane(Ï A)" methyl t-butyl ether(Ï B)îb F³f 1 mL/min î . ò "« ê 5ª ÿnf Ï Af B¢ 100 &0 ¦b j Fæ8b 15ªræ 20&80b æzÊ 2ª* Fæ8 . 0.1ª ÿn 100&0b æzÎ ê 27 ªræ 100&0 ¦b j Fæ 8b C ê¯*f 30ª VÞVÏÒ *Î(19)j ÒÏ~& .. Òò 5 O» Òò þö ÒÏB &bî oleic acid, triolein, 1,3-diolein, 1,2-diolein, 1-monoolein 5 2-monooleinj Sigma-Aldrich Chemical Co.(St. Louis, MO, USA)öB «~ HPLC ªC ö ÒÏ~& . $ Lipozyme RM IM(IM60)f Novo Nordisk Biochem North American Inc.(Franklinton, NC, USA)¦V «~ ÒÏ~&b æî Wö ÒÏB K>>Fº JÒ(Seoul, Korea) ÏF¢ «, ÒÏ~& . DAG 5 MAG F Fæ 9 R'z¢ * þê³ Î²' glycerolysis¢ Û K>>F~ DAG 5 MAG Ö 'z¢ *~ 7W þê³(central composite design)ö V¢ DAG 5 MAG F Fæ¢ W~&b, >wªC j *~ SAS(statistical analysis system) *Î(18)j Ï ~&b 4Nö >wj ÒV * Mathematica 4.0 * Îj '' ÒÏ~& . ëã(º)æ>º >wNê(35-75oC, X1), >w*(1-11*, X2) 5 >wÏ hexane~ b · (0-2 mL, X3)îb ''~ ëãæ> f Table 1" ? −2, −1, 0, 1, 2 5ê ¦^z~ þJê~ ''~ 16B ~ J;B öB þj >¯~& . Ò «³(>w)æ> (Yn)Bº K>>F~ glycerolysisö ~ 1,3-DAG(Y1), 1,2DAG(Y2), C DAG(Y3), MAG(Y4), 5 C DAG + MAG~ W ·(Y5)b ~& .. Ö 5 8 1,3-DAG 9 R'z K>>F¢ öò 1,3-DAG W 'z¢ *~ 7 W þê³ö V Ö öB ÖB 1,3-DAG ï ª C Ö"º Table 2" ?~b JêB þöB~ >w f Fig. 1ö ¾æÚî . $ ^ &æ ºæ> >wNê (35-75oC, X1), >w*(1-11*, X2) 5 >wÏ hexane~ b ·(0-2 mL, X3)ö V >w²æ(20)f Table 3ö ¾ æÚî . 1,3-DAG Wö ®Ú R2º 0.8615î F~Wf 0.0487b 5% Ú~ F~>&öB ;>î . >wªC Ö" &8" ²8j r > ìº nË6(saddle point)j ¾æÚÚ ËFªCj ¯~& . Ö" þê³ º* Úö B >wNê(44.92oC), >w*(10.24*) 5 >wÏ hexane ~ b ·(1.16 mL)öB 20.43 area% &8j ¾æÚîb >wNê(44.62oC), >w*(1.78*) 5 >wÏ hexane ~ b ·(0.87 mL)öB 2.42 area%~ ²8j ¾æÚî. (Table 4). 1,3-DAG Wö ~º ºæ> ~ 'Ëj ÚÚ Ö" Table 5f ? >w*ö & F-ratio& 8.63bB 5% Ú~ F~>&öB F~W ;>Ú >w*~ 'Ë j ² A~b >wNêf hexane~ Î&ï~ F-ratio& ' ' 1.91, 0.34 ¾æÚÚ J;B º* ÚöB 1,3-DAG Öö ~º 'Ëf 'î .. >wR ª+j * 9 îB& ®º 25 mL vialö >w Vî K>>F 2 g" & Ò^ 0.1 g(2&1 ÖjN)j b ê hexane(X3)j þê³ ö V¢ b ê DAG" MAG Wj * glycerolysis /. RM Î² 0.1 g(>wVî K>>F Z²~ 5%)¢ ÒÏ~ æîj W~& . $ magnetic barf stirrer¢ ÒÏ~ v>³ê¢ 400 rpm Fæ~ N>¢ ÒÏ~ ö V >wNê¢ ¢;~² Fæ 8 . 7Wê³ö V ëãæ> >wNê(X1), >w*(X2) 5 hexane~ b ·(X3) Table 1. Levels of independent variables for central composite design Independent variables o. Incubation temp. ( C) Incubation time (hr) Hexane (mL). Xi X1 X2 X3. Levels -2. -1. 0. 1. 2. 35 1 0. 45 3.5 0.5. 55 6 1. 65 8.5 1.5. 75 11 2.

(3) >wªCö ~ monoacylglycerol 5 diacylglycerol W 'z. 719. Table 2. Experimental data under different conditions based on the central composite design for response surface analysis (Unit: area%) Independent variables1). Response variables. Temp. (oC). Time (hr). Hexane (mL). 1,3-DAG. 1,2-DAG. Total DAG2). MAG. Total DAG+MAG3). 45 (-1)4) 65 (1) 45 (-1) 65 (1) 45 (-1) 65 (1) 45 (-1) 65 (1) 55 (0) 55 (0) 35 (-2) 75 (2) 55 (0) 55 (0) 55 (0) 55 (0). 3.5 (-1) 3.5 (-1) 8.5 (1) 8.5 (1) 3.5 (-1) 3.5 (-1) 8.5 (1) 8.5 (1) 6 (0) 6 (0) 6 (0) 6 (0) 1 (-2) 11 (2) 6 (0) 6 (0). 0.5 (-1) 0.5 (-1) 0.5 (-1) 0.5 (-1) 1.5 (1) 1.5 (1) 1.5 (1) 1.5 (1) 1 (0) 1 (0) 1 (0) 1 (0) 1 (0) 1 (0) 0 (-2) 2 (2). 7.56 10.45 18.18 17.25 8.65 11.59 21.65 14.65 17.10 17.14 9.80 18.04 7.14 17.69 15.47 14.57. 12.60 20.59 19.26 18.08 15.51 19.50 22.54 19.46 27.16 27.60 12.23 20.77 11.20 23.12 22.60 20.86. 20.16 31.04 37.44 35.33 24.16 31.09 44.19 34.11 44.26 44.74 22.03 38.81 18.34 40.81 38.07 35.43. 2.21 6.78 6.87 8.91 3.63 6.07 8.32 6.31 8.62 8.05 5.51 6.15 2.83 6.92 8.92 6.85. 22.37 37.82 44.31 44.24 27.79 37.16 52.51 40.42 52.88 52.79 27.54 44.96 21.17 47.73 46.99 42.28. 1). Values in parentheses are the coded symbols of levels of independent variables. 1,3-Diacylglycerol and 1,2-diacylglycerol. 3) 1,3-Diacylglycerol, 1,2-diacylglycerol, and monoacylglycerol. 4) Coded values of incubation temperature (oC), incubation time (hr), and content of hexane (mL). 2). '' 56.32oC, 6.95* 5 1.04 mL öB 1,2-DAG ï 26.78 area% ¾æÒb ²~º ºæ>& '' 40.92oC, 2.46*, 0.94 mL öB 6.32 area%¢ ¾æÚî (Table 4). 1,2-DAG Wö ®Ú WNê, *~ F-ratio& '' 6.83, 7.56bB 5% Ú~ F~>&ö F~W ;>Ú WN ê, W*ö 'Ëj " A~ hexane Î&ïf ² ' Ëj ~æ p~ . ¯, >wNê 5 >wÏ Î&ï ; B çöBº Wï >w*ö 'Ëj A~b >wN ê¢ B ºæ> j ;z Î çöBº Wï >w*ö ² 'Ëj A~ (Table 5).. Fig. 1. Response surface for 1,3-diacylglycerol content at constant values (5, 10, and 15 area%) as a function of incubation temperature, incubation time, and hexane content.. 1,2-DAG 9N~ æz DAG, MAG¢ F Fæ Bö ®Ú >wNê, >w*, hexane Î&ï æzNö V¢ WB 1,2-DAG Öïf Table 2, >wf Fig. 2ö ¾æÚîb >w²æf Table 3f ?~ . R2º 0.8775¢ ¾æÚî F~Wf 0.0353¢ &b 5% Ú~ F~>&öB ;>î . ;ç6f &6 ;¢ ¾æÚîb >wNê, >w* 5 hexane Î&ï. + DAG 9 R'z \ ''~ ö V 1,2 5 1,3-DAG Wï" >w²æ f Table 2 5 Table 3ö ¾æÚîb ²æ~ R2º 0.9074 ¢ ¾æÚî F~Wf 0.0166¢ &b 5%Ú~ F~> BöB ;>î . $ >wj Fig. 3ö ¾æÚî . ²~º >wNê(42.65oC), >w*(2.09*) 5 hexane Î& ï(0.91 mL) öB 9.06 area%¢ ¾æÚîb &~º > wNê(53.82oC), >w*(8.03*) 5 hexane Î&ï(1.08 mL) öB 45.09 area%¢ & ;ç6f &6 ¾æÚî. (Table 4). $ C DAG~ Wö & ëãæ>~ 'Ëf > w*, >wNê, >wÏ Î&ï~ F-ratio& '' 12.10, 6.14, 1.15B C DAG Wö ®Ú 'Ëêº >w*, >wNê, >wÏ ~ Î&ï Bb ªC>î (Table 5). ãËf C DAG Wï~ Ã&ö ®Ú >w* 7º æ>¢º Ferreira-Dias (21)~ Ö"f FÒ~& . MAG 9N~ æz. þöB~ >wf Fig. 4ö ¾æÚî . $ º æ>ö V MAG WN æzº Table 2ö ¾æÚîb ².

(4) ®"²æ B 36 ² B 5 ^ (2004). 720. Table 3. Taylor second equations calculated by response surface methodology program Taylor second equation1). Response. R2. Significance. 1,3-DAG. Y1 = −61.480950 + 1.533175X1 + 7.542900X2 + 13.456000X3 − 0.008000X − 0.068800X1X2 − 0.188200X22 − 0.150500X1X3 − 0.136000X2X3 − 2.100000X32. 0.8615. 0.0487. 1,2-DAG. Y2 = −123.743300 + 3.781700X1 + 9.962100X2 + 18.083500X3 − 0.027200X12 − 0.081200X1X2 − 0.408800X22 − 0.147500X1X3 + 0.284000X2X3 − 5.650000X32. 0.8775. 0.0353. Total DAG. Y3 = −185.224250 + 5.314875X1 + 17.505000X2 + 31.539500X3 − 0.035200X12 − 0.150000X1X2 − 0.597000X22 − 0.298000X1X3 + 0.148000X2X3 − 7.750000X32. 0.9074. 0.0166. MAG. Y4 = −42.741338 + 1.104775X1 + 4.263800X2 + 9.941000X3 − 0.006263X12 − 0.034900X1X2 − 0.138400X22 − 0.154500X1X3 − 0.186000X2X3 − 0.450000X32. 0.9099. 0.0154. Total DAG + MAG. Y5 = −227.965588 + 6.419650X1 + 21.768800X2 + 41.480500X3 − 0.041463X12 − 0.184900X1X2 − 0.735400X22 − 0.452500X1X3 − 0.038000X2X3 − 8.200000X32. 0.9315. 0.0072. 2 1. 1). X1: incubation temperature (oC), X2: incubation time (hr), X3: adding amount of hexane (mL).. Table 4. Predicted levels of mono- and di-acylglycerol production conditions of the optimum responses by the ridge analysis 1,3-DAG. Condition. Max.. o. Temp. ( C) Time (hr) Hexane (mL) Responses Morphology. Min.. 44.92 44.62 10.24 1.78 1.16 0.87 20.43 2.42 Saddle point. Total DAG1). 1,2-DAG Max.. Min.. 56.32 40.92 6.95 2.46 1.04 0.94 26.78 6.32 Maximum point. Max.. Min.. 53.82 42.65 8.03 2.09 1.08 0.91 45.09 9.06 Maximum point. Total DAG + MAG2). MAG Max.. Min.. 64.14 43.61 7.00 1.97 0.13 0.84 9.57 0.45 Saddle point. Max.. Min.. 54.07 42.84 7.98 2.07 1.02 0.89 53.54 9.56 Maximum point. 1). 1,3-Diacylglycerol and 1,2-diacylglycerol. 1,3-Diacylglycerol, 1,2-diacylglycerol, and monoacylglycerol.. 2). Table 5. Regression analysis for regression model of 1,3-DAG, 1,2-DAG, total DAG, MAG, and total DAG + MAG production Processing conditions o. Incubation temp. ( C) Incubation time (hr) Hexane (mL). F-ratio 1,3-DAG 1.91 8.631) 0.34. 1,2-DAG 1). 6.83 7.561) 1.33. Total DAG 1). 6.14 12.102) 1.15. MAG 1). 5.60 11.292) 1.75. Total DAG + MAG 8.371) 16.762) 1.44. 1). Significant at 5% level. Significant at 1% level.. 2). æ~ R2º 0.9099îb F~Wf 0.0154b 5% Ú~ F~>&j & (Table 3). r .GB ;ç6f nË6æ ËFªCj Ö", r &8f 9.57 area% .G >î . r Wf >wNê 64.14oC, >w* 7.00* 5 >wÏ hexane~ b · 0.13 mLî . $ ²~ º ºæ> 43.61oC, 1.97*, 0.84 mL öB 0.45 area%î (Table 4). ''~ ºæ> ~ Taylor 2N O; ö & 'Ëj ÚÚ >w*, >wNê Bb 'Ëj A~b >wÏ ~ Î&ïö & 'Ëf £® (Table 5). + DAG + MAG 9 R'z \ SAS *Îj Ï ²æªC Ö"º Table 3" ?~ b .GB ;ç6f '6j ¾æÚî . '6j ¾æÚ º ºæ> f 54.07oC, 7.98*, 1.02 mLîb r .GB 8f 53.54 area%î . $ ËFªCj Ï ² ~¢ ªC Ö" 42.84oC, 2.07*, 0.89 mL öB 9.56 area% .G>î (Table 4). ²æ~ R2º 0.9315îb F ~Wf 0.0072b 1% Ú~ F~>&öB ;>î . ²æ ö & ëãæ>~ 'Ëê¢ ÚÚ F-ratio& ºæ> >wNê, >w* 5 hexane Î&ï öB 8.37. (p < 0.05), 16.76(p < 0.01), 1.44j &b ¢ ÚÚ Ö" ²æö & ëãæ> 'Ëêº >w*, >wNê, hexane Î&ï Bb ²æö 'Ëj "º ©b ªC>î . *~. þ ÚÏj « Ö" «³æ> 1,3-DAG, 1,2-DAG, C DAG, MAG 5 C DAG + MAG~ Îv ''~ ²æö & ºæ> ~ 'Ëêö ;êö Nº ®æò >w*, > wNê Bb ²æö 'Ëj b¾ >wÏ ~ Î&ï ~ 'ËWf 'f ©b ªC>î (Table 5). $ ;&ªC " ËFªCj Û þê³ º* ÚöB~ ºæ>~ æz ö V ëãæ>~ &, ² j ÚÚ" > ®îb * þöB Ö"¢ á¶ ~º RSM O»j Û K>>F ~ C DAG + MAG W 'z f ²ª >wVö K> >Ff &Ò^j 2 : 1 Ö jN b ê >w/ Lipozyme RM IMj K>>F Z²~ 5% If ;B ". þê³ º* ÚöB >wNê, >w* 5 >wÏ hexane Î&ï '' 54.07oC, 7.98*, 1.02 mL þ öB & ~º 53.54 area%b .G>î . º Park" Lee(22) >w Ï ¢ Î&~æ pf " &Ïï ²ª >wV¢ ÒÏ glycerolysis >wö ~~ 48* ê C DAG + MAG ï 54.30% Fæ¢ Ö f jv~ Î²ï" v>³ê.

(5) >wªCö ~ monoacylglycerol 5 diacylglycerol W 'z. 721. Fig. 2. Response surface for 1,2-diacylglycerol content at constant values (10, 17, and 24 area%) as a function of incubation temperature, incubation time, and hexane content.. Fig. 4. Response surface for monoacylglycerol content at constant values (2, 5, and 8 area%) as a function of incubation temperature, incubation time, and hexane content.. Fig. 3. Response surface for 1,3-diacylglycerol and 1,2diacylglycerol content at constant values (20, 30, and 40 area%) as a function of incubation temperature, incubation time, and hexane content.. Fig. 5. Response surface for 1,3-diacylglycerol, 1,2-diacylglycerol and monoacylglycerol content at constant values (20, 30, 40, and 50 area%) as a function of incubation temperature, incubation time, and hexane content.. ¢ Ã&Î , >wÏ hexane Î& 5 * ö B FÒ Ö" 8j .G > ®î .. (Y4), 5 C DAG + MAG~ W ·(Y5)~ W 'z¢ >w ªCj Ï~ ÎîVç ~&b >wNê(35-75oC, X1), >w*(1-11*, X2) 5 hexane~ b ·(0-2 mL, X3)j æ > 7Wê³b 'z þ~& . 1,3-DAGº > wNê(44.92oC), >w*(10.24*) 5 hexane Î&ï(1.16 mL) öB 20.43 area% &8j ¾æÚîb 1,2-DAG º 56.32oC, 6.95* 5 1.04 mL öB 26.78 area% &. º. £. Lipozyme RM IM Î²' / ¢ ÒÏ glycerolysisö ~ K>>F¦V 1,3-DAG(Y1), 1,2-DAG(Y2), C DAG(Y3), MAG.

(6) ®"²æ B 36 ² B 5 ^ (2004). 722. 8j .G > ®î . C DAGº 53.82oC, 8.03* 5 1.08 mL þ öB 45.09 area% &8j & . $ MAG Ö 'f 64.14oC, 7.00* 5 0.13 mLöB &8 9.57 area% .G>îb C DAG + MAG Ö 'f 54.07oC, 7.98*, 1.02 mLîb r .GB 8f 53.54 area%î .. 6Ò~ º æ¦ ~òVFêÒë~ æöö ~~ Úê ©«î (02-PJ1-PG11-VN02-SV04-0009).. ^. ò. 1. Kang ST, Yamane T. Effect of temperature on diacylglycerol production by enzymatic solid-phase glycerolysis of hydrogenated beef tallow. Korean J. Food Sci. Technol. 26: 567-572 (1994) 2. Maki KC, Davidson MH, Tsushima R, Matsuo N, Tokimitsu I, Umporowicz DM, Dicklin M R, Foster GS, Ingram KA, Anderson BD, Forst SD, Bell M. Consumption of diacylglycerol oil as part of a reduced-energy diet enhances loss of body weight and fat in comparison with consumption of triacylglycerol control oil. Am. J. Clin. Nutr. 76: 1230-1236 (2002) 3. AOCS. DAG and Food Formulation. p. 550. American Oil Chemical Society, Champaign, IL, USA (2002) 4. Lee JS, Jang Y, Yang TH. Low-calorie Structured Lipids Synthesis by Enzymatic Transesterification. Korea Ministry of Agriculture and Forestry, Kyonggi, Korea. pp. 9-17 (1999) 5. Kwon SJ, Han JJ, Rhee JS. Production and in situ separation of mono- or diacylglycerol catalyzed by lipase in n-hexane. Enzyme Microb. Technol. 17: 700-704 (1995) 6. Yang B, Harper WJ, Parkin KL, Chen J. Screening of commercial lipases for production of mono- and diacylglycerols from butter oil by enzymic glycerolysis. Int. Dairy J. 4: 1-13 (1994) 7. Rosu R, Uozaki Y, Iwasaki Y, Yamane T. Repeated use of immobilized lipase for monoacylglycerol production by solid-phase glycerolysis of olive oil. J. Am. Oil Chem. Soc. 74: 445-450 (1997) 8. Boruscheuer UT. Lipase-catalyzed syntheses of monoacylglycerols. Enzyme Microb. Technol. 17: 578-586 (1995). 9. Park KJ, Ahn EY, Kwon GS, Kim KS, Kang ST. Diacylglycerol production by enzymatic glycerolysis of soybean oil. Korean J. Microbiol. Biotechnol. 32: 84-90 (2004) 10. Lee GD, Lee JE, Kwon JH. Application of response surface methodology in food industry. Food Sci. Ind. 33: 33-45 (2000) 11. Sung NK. SAS/STAT Regression Analysis. Freedom Academy, Seoul, Korea. pp. 237-286 (2000) 12. Jeong YJ, Lee GD, Kim KS. Optimization for the fermentation condition of persimmon vinegar using response surface methodology. Korean J. Food Sci. Technol. 30: 1203-1208 (1998) 13. Bae DK, Choi HJ, Son JH, Park MH, Bae JH, An BJ, Bae MJ, Choi C. Optimization for the process of ethanol extracts of persimmon leaf using response surface methodology. J. Korean Soc. Agric. Chem. Biotechnol. 43: 218-224 (2000) 14. Lee DS, Noh BS, Bae SY, Kim K. Characterization of fatty acids composition in vegetable oils by gas chromatography and chemometrics. Anal. Chim. Acta. 358: 163-175 (1998) 15. Naz S, Sheikh H, Siddiqi R, Sayeed SA. Oxidative stability of olive, corn and soybean oil under different conditions. Food Chem. 88: 253-259 (2004) 16. A Food Distribution Yearbook. Food Journal, Seoul, Korea. pp. 292-299 (2002) 17. Lee GD, Kim JS, Kwon JH. Monitoring of dynamic changes in maillard reaction substrates by response surface methodology. Korean J. Food Sci. Technol. 28: 212-219 (1996) 18. SAS Institute, Inc. SAS User's Guide. 4th ed., Vol. 2. Statistical Analysis System Institute, Cary, NC, USA (1998) 19. Foglia TA, Jones KC. Quantitation of neutral lipid mixtures using HPLC with light scattering detection. J. Liq. Chromatogr. Rel. Technol. 20: 1829-1838 (1997) 20. Bae DK, Choi HJ, Son JH, Park MH, Bae JH, An BJ, Bae MJ, Choi C. Optimization for the process of extracts of persimmon leaf using response surface methodology. J. Korean Soc. Agric. Chem. Biotechnol. 43: 218-224 (2000) 21. Ferreira-Dias S, Correia AC, Baptista FO, Fonseca MMR. Contribution of response surface design to the development of glycerolysis systems catalyzed by commercial immobilized lipases. J. Mol. Catal. Enz. 11: 699-711 (2001) 22. Park RK, Lee KT. Synthesis and characterization of mono- and diacylglycerol enriched functional oil by enzymatic glycerolysis of corn oil. Korean J. Food Sci. Technol. 36: 211-216 (2004) (2004j 7ú 1¢ %>; 2004j 9ú 16¢ j).

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