A Major Antioxidative Components and Comparison of Antioxidative Activities in Black Soybean

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(1)KOREAN J. FOOD SCI. TECHNOL. Vol. 37, No. 1, pp. 73~77 (2005). ©The Korean Society of Food Science and Technology. ¦;~ "º Öz öbî 5 Öz Î~ jL B.\Á²jÁ'*1Á;«2Á^%** *L ®\²Á®«¦Á:J

(2) Ê²Ò\b8 1 ã\L ®'·, 2â¿L £¶öBB. A Major Antioxidative Components and Comparison of Antioxidative Activities in Black Soybean Sun-Hee Kim, Tai-Wan Kwon, Young-Soon Lee1, Myoung-Gun Choung2, and Gap-Soon Moon* Food Science Institute, School of Food and life Science, and Biohealth Products Research Center, Inje University 1 Department of Food and Nutrition, Kyunghee University 2 Department of Pharmacognosy Material Development, Samcheok National University Contents of isoflavone, phenolic acids, tocopherol, and anthocyanin in black soybean (Glycine max) were measured by HPLC. To compare antioxidative activities of main black soybean components, antioxidative effects of the same levels of commercial standard components were measured by Trolox equivalent antioxidant capacity assay (TEAC). Most effective component was gentisic acid followed by anthocyanin, p-coumaric acid, ferulic acid, genistein, syringic acid, and daidzein. TEAC assay results revealed genistein in isoflavone, gentisic acid in phenolic acids, ρ-tocopherol in tocopherol, and anthocyanin showed highest antioxidative and synergistic acitivities, with anthocyanin showing strongest synergy effect. Key words: antioxidative activity, isoflavone, phenolic acids, tocopherol, anthocyanin. *. . daidzein 5 glycitein ® . ß® genisteinf ^7ö ~ superoxide Wj ÛBÊ¾ F W Ö²«j B~ Öz Î"¢ ¾æÞ >Ú ® (5,6). $ îÖÊ b¦¢ Ï öB genisteinf «· /êB hydrogen peroxide~ Î"' ²B ·Ï~& ¶F" Fenton > wö ~ Öz' DNA~ ¶çj ïj& >Ú ®. (7,8). ~ Öz öbîB isoflavone ö phenolic acid. ê "º j ~º ©b C&^ ® f FÒç º B ester ; " Ò rJ^ ® (9). $ öº Æz¾" ?f Â ÖzB& F>Ú ®Ú &Ë 5 &"; 7 Özn;Wö V~º ©b C&rb, Ú ÚöBº WÖ²¢ ²B FÒVf "Özæî~ Wj ÛB~º Öz ·Ïj (10). ¦;~ ~¾ Ó¶~ Öz Î"¢ ¦ ®« ö" jv~&j r, ¦;~ Öz Î"& ¸² ¾æÒb æ öBº ¦;~ Öz Î"ö & ©b Îæº Öz öbî 7 genistein" daidzein ?f isoflavone" phenolic acids 5 Æz¾~ ïj G;~&, ¦; «b ï² nÆjò ïj G;~& . Ò ¦ ;~ "º Öz öbîj «~V *~ ¦;ö F>Ú ®º Öz bî ~ ï" ÿ¢ ·~ &®j Ï~ TEAC(Trolox equivalent antioxidant capacity)»b Öz Î"¢ jv~ ~ .æ Î"¢ G;~& .. ¦;f "(Leguminosae)ö ³~º 1j .b 4 RÒ ³ö 2-3r~ wï «¶& Ú ® . ¦;f & æº '·' VË öê «bö FB ßF~ ï² 6j Ã&Ê · £Î¢ B>~ A¦V Oö B £bê ÒÏ~ z (1). ¦; « f ¢> ¦" WªöB N& ì, æ «bö nÆjò F> Ú ®º © ßû . ¦;~ nÆjòf >ÏW~ Cf 'Á¶ïj º Âï²B Úö jZ ¦·Ï ì J®J Öz Î" ~ ÒW ¸f ©b rJ^ ¦ ;~ ;VËWö & &j ®¢bÊ ® (2,3). nÆjò F>Ú ®æ pº ¦öê ç Ö z bî F>Ú ®º ©b C&^ ®b, öb îº isoflavone, phenolic acids, Æz¾, phytic acid, saponin, trypsin inhibitorf jÖ 5 Ïæ > ®. (4). ö ëß~² Ò~º isoflavone bîöº genistein, *Corresponding author: Gap-Soon Moon, School of Food and Life Science, College of Biomedical Science and Engineering, Inje University, Kimhae 621-749, Korea Tel: 82-55-320-3234 Fax: 82-55-321-0691 E-mail: [email protected] 73.

(3) ®"²æ B 37 ² B 1 ^ (2005). 74. Òò 5 O». þÒò ö ÒÏ ¦;f Ó¶(Glycine max)bB 'Î ³ë²öB ª·Aj ÒÏ~& . Öz Î"¢ G;~V * ÒÏB isoflavonef phenolic acids~ &®f SigmaÒ(St. Louis, USA)öB «~&, Æz¾ &®f Merck(Germany) Ò~ Æz¾ ÿÚ j ÒÏ~& . nÆjòf Choung (11)ö ~ O»b ªÒ, ;B~ &®b ÒÏ~& . ¦; ¦~ Öz Î jL Mill(Takasaki kagaku, Japan) ªê ¦;(Ó¶)" & b ¦(ö)j 10Vï~ 80% zêR 12* &Ú "B 2² > ºÂ ê "~ 40oCöB 6{²*³» V(Buchi Laboratoriums Technik AG, Rotavapor RE-200, Germany) 6{³» r ÿÖ~ 80% zêR ºÂbj ò î . ºÂb~ TEAC valueº Rice-Evans (12,13)~ O»ö V¢ G;~& . 7 mM ABTS(2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonate)ö « ³ê& 2.45 mM >ê potassium persulfate¢ Î&~ ABTS radical cation(ABTSÁ+)j ò. î . Ïj 734 nmöB 7ê& 0.70(Û0.02) >ê ;~ 3 mL ABTS radical cation Ïö 30 µL òÏj Î&~ 30oCöB 6ª* 7ê¢ G;~& . ³êö V ò~ Öz Î"¢ Trolox ³ê jv~ ~& . ¦; Öz öbî~ ï /; Isoflavone ï /;: ªê ¦; 0.1 gj 1 N HCl 1 mL ¢ Î&~ 100oCöB 150ª* Ö&>ªÎ ê genistein" daidzein~ ïj Wang" Kuan(14)~ O»ö V¢ Symmetry C18 column(250Ü4.6 mm I.D., Waters, USA)b HPLC(PU 980, Jasco, Japan)¢ ÒÏ~ ªÒ, ;ï~& . r ÒÏ ÿçbº zêR : 1 mM .ÖzÎª(6 : 4, v/v)¢ ÒÏ~& b, F³f 0.5 mL/min ~& 254 nmöB G;~& . Tocopherol ï /;: ªê ¦; 2.5 gj 250 mL ~& 2¢Êö I 75% öêR 90 mLj & ê î²¢ Ï* B Ö²¢ BÎ r 75oC >»öB 2*ÿn ~~ï 'ÊB æÏW bî j &N ºÂ~& . ºÂj " r, j 250 mL ª³vö I 30 mL Öb 3² > ºÂ~ Æz¾[j ª³~& . Æz¾ B ÖºÂj î²Ï*Î ê 45oC >»öB 6{³». r, zêR 2 mLö Ï~ 0.45 µm "æ " ê HPLC ªC~& . Columnf µ-Porasil(300Ü3.9 mm I.D., Waters, USA), ÿçf n- Ö : ²*6R(99.5 : 0.5, v/v)¢ ª 2.0 mLO FÂV . ;7¦ÂV¢ Ï~ Excitation 300 nm, Emission 338 nmöB G;~& (15,16). Phenolic acids ï /;: ¦; ªö 0.1 gj 1 N NaOH 1 mL¢ & ê, 100oCöB 30ª* r¢Ò &>ªÎ r 6 N HClb 7zÎ ê zêR 2 mL >ê ;Ï~, ç[j 0.45 µm "æ "~ HPLC ªC~& . ~ phenolic acidsB benzoic, caffeic, chlorogenic, ferulic, gentisic, p-coumaric, p-OH benzoic, salicylic, syringic, transcinnamic, vanillic acid~ ïj G;~&, Symmetry C18 column(250Ü4.6 mm I.D., Waters, USA)j ÒÏ~& . ÿçf. v &æ Ï ¢ ÒÏ~&º AÏ º 1% .Öj, BÏ º zêR, F³f 0.8 mL/min ~& . ÿç Ï A : B~ jNf 0ªöB 100 : 0b ·~ 25.0ªræ 70 : 30, 25.1 ª¦V 40.0ªræ 40 : 60, 40.1ª¦V 50.0ªræº 0 : 100b gradient~ 11«~ phenolic acid¢ ªÒ ;ï~& (17). ¦; «b~ anthocyanin ï /;: ¦;~ «b(0.1 g) òj ªÒ ê 1% HCl FB 40% zêR 30 mL Î&~ 4oCöB 24* Ú ï²¢ ºÂ~& . ºÂB ï²º 0.45 µm "æ " r HPLC ªC~& (11). ¦;~ Öz Î~ /; Isoflavone, phenolic acids 5 Æz¾~ &®" ¦;(Ó ¶) «böB ºÂ nÆjò ï² ºÂbj ¦;ö F>Ú ®º ÿ¢ ·b TEAC»b Öz Î"¢ G; ~& (12,13). ¦;ö F* Öz öbî~ .æ Î /; Anthocyanin, genistein, gentisic acid 5 γ-Æz¾j ¦; ö Ú®º ïö ÿ¢~² b~ ~ .æ Î"¢ TEAC»ö V¢ G;~& . Ûê¾Ò. þÖ"~ Ûê¾Òº SPSS programj Ï~ ªC~ meanÛSD ~&b, ' * ï~~ Ûê' F~Wf one-way ANOVA ¦Ã r α = 0.05 >&öB Duncan’s multiple range testö ~ Òê ¦Ã~& .. Ö 5 V ¦; ¦~ Öz Î þöBº ¦;(Ó¶)~ Öz Î"¢ ¦(ö )" jv G;~V * ¦;" ¦j 80% zêR ºÂ~ ºÂb~ Öz Î"¢ TEAC»b jv G; Ö"º Fig. 1" ? . Fig. 1öB º :f ? ¦ ºÂb~ ³ê& 0.1%, 0.5%, 1.0%¢ r TEAC value& 0.10, 0.43, 0.90 mM Trolox equivalent& ¦; ºÂböBº 0.12, 0.55. 1.10 mM Trolox equivalent¢ ¾æÚî . ³ê¢ Ò ~ ê ¦; ¦ Öz Î"& ¸~b ³ê& Ã &> ¦;" ¦~ Öz Î" N& . ¦; ¦ ¸f Öz Î"¢ ¾æÚº ©f phenolic compoundf ¦; «b ï² nÆjò bî çß·Ï ~ Öz Î"¢ ¾æÚº ©b º;>Úê . Öz Î"¢ G; TEAC»f .ËöB ABTS~ ·N ¢:¢~ 7ê& ÖzBö ~ ÛB>º ©ö V.~ BB>î Ú¾ ÖzB~ ËKj Trolox~ 8" jv~ ¾æÚ&b(12,13), in vivoöB~ C ÖzË G;öò jî¢ in vitroöBê ÖzËj G;~V * O»bê 6Ò Ï> ® (18). $ Moon (19)f ~ Öz Î "¢ G;~º &Ë ' þO»j {ã~V * DPPH », FRAP», TEAC»j Ï~ ~ Öz öbîj &®j Ï~ G; Ö" TEAC»~ ãÖ glutathione~ Î "¢ 6æ > ®j öò jî¢ ~ "º Wª isoflavone " &¦ª~ phenolic acids~ Wj ï& > ®Ú ~ Öz Î" G;ö &Ë ±f O»b ~ ® ..

(4) ¦;~ "º Öz öbî 5 Öz Î"~ jv. 75. Table 2. Contents of phenolic acids in black soybean (Glycine max) Phenolic acids p-OH benzoic acid Gentisic acid Chlorogenic acid Vanillic acid Caffeic acid Syringic acid p-Coumaric acid Ferulic acid Benzoic acid Salicylic acid trans-Cinnamic acid Fig. 1. Comparison of antioxidant activities of soybeans methanol extracts (80%) in different concentrations. Table 1. Contents of isoflavone and tocopherol in black soybean (Glycine max) Components Isoflavone. Tocopherol. Black soybean (mg%) Genistein Daidzein. 43.86 31.73. Total. 75.59. α-tocopherol β-tocopherol γ-tocopherol δ-tocopherol. 01.99 00.47 10.68 03.95. Total. 17.09. ¦; Öz öbî Isoflavone ï: HPLC ªC ¦;~ isoflavone ïj Table 1ö ¾æÚî . ò ÒÏ Ó¶öº genistein 43.86 mg%, daidzein 31.73 mg% F>Ú ®î . Choi (20)ö ~~ ¦;~ genistein 5 daidzein ï '' 31.8 5 37.8 mg%î ~ þöB G; ï" F Ò ©b ¾æÒ . isoflavone ïf ~ ®«, ÒVê, ÒVæ, ¦*, W?Vö V¢ N¢ ~& (21). Tocopherol ï: Ó¶~ Æz¾ ïj HPLC ªC Ö"¢ Table 1ö ¾æÚî . HPLC ªÒ NZf α-, β-, γ-, δ-Æz¾ Bb ÏÂ>î ¦;~ ÿÚê ïj G; Ö", α-Æz¾ 1.99 mg%, β-Æz¾ 0.47 mg%, γ-Æ z¾ 10.68 mg%, δ-Æz¾ 3.95 mg%& F>Ú ®b, ÿÚê ïf γ- > δ- > α- > β-Æz¾ Bî . Lee (22) 13«~~ ~ Æz¾ ïf «~ö V¢ ï~ N& ô ¾æÂ ~& . Phenolic acids ï: Ó¶ö F>Ú ®º phenolic acids ïj Table 2ö ¾æÚî . Phenolic acids &®~ HPLC öB~ ªÒNZf p-OH benzoic, gentisic, chlorogenic, vanillic, caffeic, syringic, p-coumaric, ferulic, benzoic, salicylic, transcinnamic acid Bb ÏÂ>î . ¦;~ phenolic acids~ ïf benzoic(126.70 mg%) > p-coumaric(67.68) > salicylic(59.40) > gentisic(43.19) > ferulic(16.57) > syringic(15.04) > chlorogenic. Total. Black soybean (mg%) 2.47 43.19 8.00 2.82 4.53 15.04 67.68 16.57 126.70 59.40 1.00 347.40. Table 3. Contents of anthocyanin in black soybean (Glycine max) seed coat Anthocyanin. Black soybean seed coat (mg/g). Delphinidin 3-glucoside Cyanidin 3-glucoside Petunidin 3-glucoside. 1.42 5.77 0.30. Total. 7.49. (8.00)> caffeic(4.53) > vanillic(2.82) > p-OH benzoic(2.47) > transcinnamic acid(1.00)~ Bb benzoic, p-coumaric 5 salicylic acid ï jv' ô~, vanillic, p-OH benzoic 5 transcinnamic acid~ ï Ô~ . Prattf Birac(23)f " B ®öB "º ÖzB chlorogenic acid, caffeic acid, ferulic acid 5 p-coumaric acid¢ ªÒ~& Pratt (24)f caffeic acid 3.6Ü10−3, ferulic acid 1.5Ü10−4, syringic acid 1.8Ü10−4, vanillic acid 1.2Ü10−5 moles/kg, p-coumaric acid, gentisic acid, p-OH benzoic acidº ï Ò~& ~& . Seo (25)f Wî B®b¦V phenolic acidf isoflavonej HPLC ªC~&º îæ &v;~ ãÖ p-OH benzoic acid f gentisic acid~ 7.5Û6.2, vanillic acidf caffeic acid~ 129Û15.7, syringic acid 221Û24.3, p-coumaric acid 122 Û5.5, ferulic aicd 215Û11.4, salicylic acidf isoferulic acid 162Û48.5, sinapic acid 216Û21.6& F>Ú ®Ú C 1134Û 63.2 µg/g~ phenolic acids~ Ò¢ ~&b, ö F> Ú ®º phenolic acids~ «~º ~ jÝ~² >Ú ®r j r > ®î . Anthocyanin ï: Ó¶ «b~ nÆjò ïf Table 3ö ¾æÚî . «bö F>Ú ®º nÆjòöº delphinidin 3-glucoside, cyanidin 3-glucoside 5 petunidin 3-glucoside & g '' 1.42, 5.77, 0.30 mg F>Ú ®î . Choung (11) 10«~~ ¦; «b~ nÆjò ïj G; Ö" C nÆjò ï 1.58-20.18 mg&b, delphinidin 3-glucosideº 0-3.71 mg, cyanidin 3-glucosideº 0.94-15.98 mg 5 petunidin 3-glucosideº 0-1.41 mg F>Ú ®î ~& . þöB ÒÏ Ó¶ «böê 3B~ B. nÆjò F>Ú ®rj { > ®îb nÆ jò ï² B*f 7, Nê, ^Ò, '·ö ~ ~ãº.

(5) ®"²æ B 37 ² B 1 ^ (2005). 76. Table 4. TEAC values1) of anthocyanin, isoflavone, phenolic acids and tocopherol in black soybean Components. TEAC Value (mM). Anthocyanin. 1.516Û0.006g2). Genistein Daidzein. 0.684Û0.004d 0.673Û0.007d. Gentisic acid p-Coumaric acid Ferulic acid Syringic acid Caffeic acid Chlorogenic acid Vanillic acid p-OH benzoic acid Salicylic acid Benzoic acid trans-Cinnamic acid. 3.428Û0.009h 1.362Û0.004f 1.104Û0.004e 0.677Û0.006d 0.199Û0.004bc 0.180Û0.006bc 0.178Û0.007bc 0.024Û0.007a 0.009Û0.004a 0.006Û0a 0.006Û0.004a. α-tocopherol β-tocopherol γ-tocopherol δ-tocopherol. 0.049Û0.003a 0.035Û0.008a 0.251Û0.004c 0.125Û0.004b. 1). Data indicate meansÛS.D. Values with different superscript within in a column are significant difference (p<0.05) by Duncan’s multiple range test.. 2)a-h. ö *&® 'Ëj Aº ©b rJ^ ®b, ö V¢ ïöê N& ¾æÂ © ? . ¦;~ "º Öz öbî~ Öz Î ¦;ö F>Ú ®º "º Öz &Nbî~ Öz Î "¢ TEAC»b G;~ Table 4ö ¾æÚî . ¦;ö F>Ú ®º nÆjò, isoflavone, phenolic acids 5 Æz¾ ~ Öz Wj G; Ö", phenolic acids 7 gentisic acid~ TEAC value& 3.428Û0.009 mM Trolox equivalent & Ë ¸~ «b~ nÆjò~ TEAC valueê 1.516Û0.006 mM Trolox equivalent ¸f Öz Wj ¾æÚî . Phenolic acids~ Öz Î"º gentisic > p-coumaric > ferulic> syringic > caffeic > chlorogenic > vanillic > p-OH benzoic > salicylic > benzoic acidBî . Kim(26)f Z> &vFf &vF-b emulsion systemöB ¾¦zb~ Öz Î"¢ jv Ö" caffeic acid, chlorogenic acid, gentisic acidö ; Öz Î" & ®rj ~&b, Lee (27)ö ~~ linoleic acidemulsionöB caffeic acid& chlorogenic acid ÖzË ¸. ~& . þöBê chlorogenic acid& caffeic acid ïf ô~æò jÝ ÖzËj ¾æÚÚ caffeic acid & chlorogenic acid Öz Î"& ¸rj º; > ®î. . þöBº ß® gentisic acid& Ö ¸f Öz Î" ¢ ¾æÚÚ ö Ò~º phenolic acidö j ¦; ~ Öz Î"ö 7º j ©b Îê . ¦ ;ö F>Ú ®º phenolic acids 7ö benzoic acid& &Ë ô F>Ú ®îæò Öz Wf Ö Ô² ¾æÒ ï &Ë 'f trans-cinnamic acidê Öz W Ö Ô~. . $ hydroxyl(OH)V 2B¢ &ê gentisic acid& 1B~ OH V¢ &ê p-coumaric acid ïf 'îb¾ Öz W. Fig. 2. Synergic effect of anthocyanin, genistein, gentisic acid and γ-tocopherol determined by TEAC assay. 1: Anthocyanin 2: Genistien 3: Gentisic acid 4: γ-tocopherol. 1) Observed values measured in combinations of compounds. 2) Calculated values indicate the sum of individual antioxidant effect obtained at the same addition level.. f ¸rj r > ®î . ¦;öê çï~ phenolic acid F>Ú ®bæ phenolic acid~ Ò ;, ï¾ . phenolic acid~ Öz Î"ö & & jº © . Genistein" daidzeinº 0.684Û0.004, 0.673Û0.007 mM Trolox equivalent nÆjò, gentisic acid, p-coumaric acid, ferulic acid º Ôf Wj ¾æÚîb, Æz¾öBº γ- > δ> α- > β-Æz¾ Bb Öz Î"& ¸² ¾æÒ . Æz ¾~ Öz Î"º δ- > γ- > β- > α-Æz¾~ BB rJ ^ ®b¾(28), ¦;ö F>Ú ®º Æz¾ ïj & Öz Î"¢ G; öBº Æz¾~ ï" jf ~ Öz Î"¢ ¾æÚî . ¦;ö F* Öz öbî~ .æ Î Ó¶~ "º Öz öbîf nÆjò" isoflavone 7 genistein, phenolic acids 7öBº gentisic acid, Ò Æz ¾öBº γ-Æz¾î . J «~~ bîj ¦; ö Ú®º ïö jf~ê B~ ~ .æ Î" ¢ G; Ö"º Fig. 2f ? . ~ .æ Î"¢ ÚÚ V * v «~öB J «~ zbj b~ TEAC»b G; Ö" nÆjò, gentisic acid 5 γ-Æz¾j b ®j r G;8" .ç>º 8~ N& &Ë ô ¾æÂ >, genistein" γ-Æz¾~ Nº ~ ¾æ¾æ p~ . $ nÆjòj B ¾^æ ^ «~ zbj b~& j rº .ç>º .æ Î"f B G;B 8~ N& & Ë 'î . nÆjò" γ-Æz¾j b~&j r .æ Î"~ Ã&Nf 35.04Û0.23% &Ë ¸~b, nÆjò" genistein~ Ã&Nê 27.30Û0.33% ¸~ . G;8" .ç> º 8~ N& &Ë ô Â nÆjò, gentisic acid 5 γÆz¾j bbf 22.9Û0.21%~ Ã&Nj ¾æÚîb J «~~ bbf 17.44Û0.16%¢ ¾æÚî . $ v «~~ bb~ .æ Î" Ã&NöBº nÆjòj b~&j rò 20% >º Ã&Nj ¾æÚî . f ? nÆjò b~&j r& &Ë ¸f .æ Î"¢ ¾æÚÚ nÆj òf ¦;~ "º Öz Î"~ öbî~ j ö ò jî¢ phenolic bî " .æÎ"¢ Û z× z Öz Î"ö V~º ©j r > ®î ..

(6) ¦;~ "º Öz öbî 5 Öz Î"~ jv. º. £. ¦;ö F>Ú ®º Wª 7 "º Öz öbîj «~V *~ Ó¶~ isoflavone, Æz¾, phenolic acids 5 nÆjò~ ïj G;~& . Ö" genistein 43.86 mg%, daidzein 31.73 mg% F>Ú ®îb, Æz¾ ïf α-Æz¾ 1.99 mg%, β-Æz¾ 0.47 mg%, γ-Æz¾ 10.68 mg%, δ-Æz¾ 3.95 mg% F>Ú ®î . 11« ~~ phenolic acidsöBº benzoic(126.70 mg%) > p-coumaric (67.68) > salicylic(59.40) > gentisic(43.19) > ferulic(16.57) > syringic (15.04) > chlorogenic(8.00) > caffeic(4.53) > vanillic(2.82) > p-OH benzoic(2.47) > trans-cinnamic acid(1.00)~ Bb F>Ú ® îb, ¦; «bö F>Ú ®º nÆjòj G; Ö " delphinidin 3-glucoside& 1.42, cyanidin 3-glucoside 5.77 5 petunidin 3-glucoside& 0.30 mg/gî . ¦;ö F>Ú ®º Öz bî (nÆjò, isoflavone, phenolic acids 5 Æz¾)j ¦;ö Ú®º ï" jf~ê B~ TEAC»b Öz Î"¢ G; Ö", genistein, gentisic acid, γ-Æz¾, nÆjò~ Öz Î"& ¸f ©b ¾ æÒ . J «~~ Öz bî ~ .æ Î"¢ ªC Ö ", f B .æ Î"& ®º ©b ¾æÒb ß® nÆjòj b r .æ Î"& &Ë ¸² ¾æ¾ ¦ ;~ Öz Î"ö nÆjò ² & ~ ®rj r > ®î .. 6Ò~ º "VF¦Á"Ò æ; æ7Kb V B&v :JÊ ²ÒbV(Biohealth Products Research Center) 5 "Ò ß;V.(R01-2000-00000187-0) j æöb >¯>î ö 6Òãî .. ^. ò. 1. Oh MK, Rhee SH, Cheigh HS. Changes of lipid composition of Korean black soybean before and after soaking. J. Korean Soc. Food Nutr. 21: 20-35 (1992) 2. Francis FJ. Future trends. pp. 233-247. In: Developments in Food Colors-2, Walford J (ed). Applied Science Publishers, New York, USA (1984) 3. Tsuda T, Shiga K, Ohshima K, Kawakishi S, Osawa T. Inhibition of lipid peroxidation and the active oxygen radical scavenging effect of anthocyanin pigments isolated from Phaseolus vulgaris L. Biochem. Pharmacol. 52: 1033-1039 (1996) 4. Hayes RE, Bookwalter GN, Bagley EB. Antioxidant activity of soybean flour and derivatives-A review. J. Food Sci. 42: 15271531 (1977) 5. Kusunoki T, Higashi H, Hosai S, Hata D, Sugie K, Mayumi M, Migawa H. 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