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Extraction and Purification of Isoflavones from Korean Soybean and Soybean Paste

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Extraction and Purification of Isoflavones from Korean Soybean and Soybean Paste HWAHAK KONGHAK Vol. 41, No. 5, October, 2003, pp. 612-616 † , 402-751 253 (2003 3 10 , 2003 7 28 !) Extraction and Purification of Isoflavones from Korean Soybean and Soybean Paste Kwang Jin Lee, Du Young Choi and Kyung Ho Row† Center for Advanced Bioseparation Technology and Department of Chemical Engineering,Inha University, 253, Yonghyun-dong, Nam-ku, Incheon 402-751, Korea (Received 10 March 2003; accepted 28 July 2003) isoflavones HPLC . !" # $ %& isoflavones ' ()* +,+- ./)01 . 60% ethanol 2$ 345 6 72' 15 µm 896 :; <= >?)@ AB +CD 5 . 5 +- '? * 24E 5%5F, genistin, daidzein, genistein* &GE 0.2 wt.%5H. I# J3 K LAMN isoflavones* &G5 B7 OP. Abstract − In this work, analytical and preparative HPLC systems were utilized to obtain isoflavones from Korean soybean and byproduct of soybean paste. The optimum operating conditions were experimentally determined to analyze and collect the isoflavones in the pretreated extract. The extraction efficiency was the most favorable at aqueous solution of 60% ethanol. Korean soybean was extracted by preparative column with 15 µm packings and linear gradient elution mode. Under these experimental conditions, the yield of solid extract was 5%, while the weight percentage of genistin, daidzein, and genistein was 0.2 wt%. The content of non-glucosides isoflavones in the fermented byproduct of soybean paste was remarkably higher than that in the Korean soybean extract. Key words: Isoflavones, Korean Soybean, Extraction, RP-HPLC 1. s]t 87[5], u vwx yz){k %|& } m7 8A [6]. yz){! ~M %<, d, q, fM ! 8 jk l Ev }, 8] g, ^ N6, ! 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WXY isoflavones daidzein, genistein, glycitein V, G) ,% <j @ , Z 0.2-0.4% [\ $%@] 87[3], ^, %NX, _`X, a Q pqr ¡ isoflavones) q, B@F X, bAcd, ef/ dg hi& jkl m7 8A[4]. opqr ¡ isoflavones, @/ ¢£,A[9]. ,& Isoflavones ! 3n opqr 7" -O-glucosides (daidzin, genistin, isoflavones! \ }=, pQ +, $@] <j '( ¤ glycitin), 9n pqr 6" -O-acetyl-glucosides (6" -O-acetyl-daidzin, ) isoflavones ¥¦u |;7 8A[9]. 6" -O-acetyl-genistin, 6" -O-acetyl-glycitin), 6" -O-malonyl-glucosides (6" - §)¨©:ª« ¬­ ®2B, ,gk 7[g |,l ¯w O-malonyl-daidzin, 6" -O-malonyl-genistin, 6" -O-malonyl-glycitin)) , F °±²;, Bp²;, ,³´^²;, B§/, pY²; V µµ "¶B) B@ ·) B [ ¸ [¹ Bº » k [Y, B V B¼ » ,;@7, ½¾& , ¿ †To whom correspondence should be addressed. E-mail: [email protected] , À B/ Á p; |;9, ,g 612 613 ® S ÂM®Ã N) ¶[; |;7 , 67 ÙÚ) BºÝ7, 15 µm ÙÚ B¼ ÝA. HPLC æ g ¿ ÂM®Ä)Å rÆ ® Ç È L 8/ ¢ ç Ê! % 1ml/min, GÕ« 20 µl, ¦! 260 nm) 7[ £ HPLCl ,;u ¬­ B É Ê a[/ Á u æçÝA. ,g ÂM®ËA[10]. %; B isoflavones Ì/ Á & HPLCl ,;& Bº N, 3 |;@7, Bº; § 3. )¨©:ª« Í §/ ²Q B\ QG L6P Î Ï Ð §/ ¢£ 7Î; Ñ ÒHA. , o Y á |;& ©â $ isoflavones $¹k BºÊ ; §)¨©:ª« 12 ¬­ :Ó ,g Ô) GÕ æç) 7Ý7 ã isoflavones â u A¹ isoflavones Ì L 8A. ÉÖ isoflavones Æ $¹ ÝA. pQ isoflavones ×g HPLCl ,;u B@]67 ,g 3 µ Bl ;u ) AØ 4n ÙÚk 15 mÕ Í> C18 3-1. isoflavones Í> ÛÜ Y; ÙÚ |;Ý9 ,g p; ©â $ isoflavones $¹ HPLCl |;u BºÝA. ) ÂMl GÜ Þ n isoflavones B¼u LC-MS) [B æç & , ©â ¥¦Ý7 ¥¦ º[11], $%@] 8 daidzein, genistein y§)¨©:ª« ×g HPLC N BºÝA. B¼; ÙÚ) Ì! ®2l l ,;u Bº[12], isoflavones $¹ HPLCl ,;u 3B Bº; HPLCl |;u BºÝA. ,g) , Q©Rzî, ,g p; k 126 ßà®2) [Bº ÝA Qzã 3B ,g ,;ÝA. Fig. 3 E, [13]. á ©â ¥¦ isoflavones Bº7 ,, ù & ¥¦ Bº; ÙÚ |;u % 1 ml/min, G ã $ isoflavones äL 7å\ B N æç Õ« 20 µl æçÊ BºÝA. ,g ÂM®ÃF ) ·, »,A. æç) ÉM ,g! 6 B A B) @÷A . ,g A /Q©Rzî/Qzã, 94.9/5.0/0.1(vol.%), B /Q 2. ©Rzî/Qzã, 5/94.9/0.1(vol.%),ÝA. ,g ! A/B 100/0-70/30(vol.%)) 60B ` ) ÂM®A. ßà®2 2-1. rÆ® o´ isoflavones! genistin,÷7 AØ B á æç |; ©â ¥¦ k ã ! (G) èG éyz ! £ E7 rÆ® u [ÝA[11, 13]. Isoflavones ) YcêëA. ßà ®2 daidzein(4,7-Dihydroxyisoflavone, 98%), 36 opqr daidzein, genistein, glycitein ', Fig. 1 gensitein(4,5,7-Trihydroxyisoflavone, 98%), genistin(4,5,7-Trihydroxyisoflavone-7- EuG7 89, Fig. 2 á ; ¥¦ ¸ [YN glucoside, 99.1%)! Sigma Co. ÕÝA. ì ®2! GÕ c[ ÝA. µ µ / í uk6(PVDF 0.45 m, Waters Co.)l ,;u ukl 15 m C18Õ Í> B¼; ÙÚ |;u æç& akl Fig. 4 ÝA. ,g |;& Qzã! JM, Q©Rzî! ïãM ÷A. Bº; HPLC ! ,g k GÕ«, %¹ ÕÝ7 ! ðÎ ñò(Waters Co.) Ò(HA-0.5 µm, Waters Ê æçÝ7, Fig. 3 Ì! ak ou «§ ] Co.)l ,;u uk& 3 dÆLl |;ÝA. 9 ÙÚ j, ðÝA. §)¨©:ª« ÙÚ |; Í> Õ §/ 6 @F daidzink glycitin, genistink 6"-o-malonyldaidzin 2-2. , µµ B@6 !! g¡) û ® ;¦@÷7 ,] 6"-o- á æç Bº; HPLC Ñ Waters 515 multi-solvent delivery malonylgenistin, ÙÚ ") #A. ¤& rÆ® o´u ßà system 486 tunable absorbance analytical detector, Rheodyne injector . [Bº L?Ý9, opqr daidzein, glycitein, (50 µl sample loop)l $& Waters model 600S liquid chromatography genistein! ©â ¥¦ $¹, $@÷A. (Waters Associates, Milford, MA, U.S.A.)l |;óA. HPLC Ì! ©â ¥¦ $ isoflavones $¹ æç) %[/ Á chromatography ! ô, Lõ Ñ(Chromate Ver. 3.0, Interface ©â 20 g 60% K L; 60 ml 7 3,000 rpm Eng., Korea)l ö Ì÷A. Õ §/ 5µm , Í> B 15® [\ ¥¦ & & B¼; ÙÚ |;u isoflavones rÆ® µ º;(RS-tech OP C18, 0.46ø25 cm)k Õ §/ 15 m(Lichrosopher (30-65B /à) õu ä' d</) ýþÝA. , µ 100RP-C18, Merck, U.S.A., 0.46ø25 cm) Í> ÙÚ |;ÝA. , Ì]> ®2l 20 ll GÕu Bº; ÙÚ ,;u ¥¦ ù ") úå Yû/ Á ü1 B/(Beckman Bº& ak Fig. 5 8A. : ak ©â 20 g 7 ¥¦ Coulter)l |;ÝA. ¥¦& ®2l ýþ/ Áu ä' d</ (BÜCHI Rotavapor R-200, Switzerland)l |;Ý7, %¦ isoflavones B¼& ÿ aÊ/(Model name: SFDSM 12, 1 Eng.) |;u ) P÷A. 2-3. ©â ¥¦ ¸ ã isoflavones ¥¦/ Á µµ 50 g k 80% èK, 80%, 60%, 40% K) g³(25 oC), 50 oC 300 ml J 7 3® 3,000 rpm) ´ ÝA. ¥¦ ; uk6 ök® úå ¸ u Yû& ÿ ýþÝ A. ©â ¥¦ k ã ¥¦ ; ü1 B/ (Beckman Coulter)l 60,000 rpm, 4 oC ä \) 1® 1 Bl ÝA. 0.45 µm Òl ök® Ì! ®2l Fig. 1. Chemical structures of isoflavones. HWAHAK KONGHAK Vol. 41, No. 5, October, 2003 614 Fig. 4. Chromatogram of isoflavones from Korean soybean by prepar- ative HPLC (15 µm, 1 ml/min, 20 µl) Fig. 2. Extraction and purification procedure from byproduct of soy- bean paste. Fig. 5. Chromatogram of fractioned isoflavones from Korean soybean by analytical HPLC (60% EtOH, 25 oC, cutting time 30-65 min). Yû/ Á / 8 "# MÙ0, , pH ù, , ³´^L6 ¸ K) isoflavones °±® K) 1±u Fig. 3. Chromatogram of isoflavones from Korean soybean by analyti- äL N, |;@7 8A[3]. cal HPLC (Water/ACN/AA 94.9/5/0.1/5/94.9/0.1, 100/0-70/30 vol.%, á ¥¦ 42 ¤ 42 L; 7, ´ k 1ml/min, 20 µl). uk "l û3A. 20-80% èK ¤ K L; |;u isoflavones 7 j) ¥¦Ý9, ¥¦ ; k ³\ . L! 5%,9, , 36 isoflavones genistin, daidzein, & I4 7u æç) Bº& akl A5 :6 ß®Ý genistein $¹! 0.2 wt.%l Ì L 8÷A. A. 80% èK L; k g³(25 oC) ã ¥¦ÝA. Fig. 6 , ¥¦ B¼; HPLC) Bº& ak,7 daidzeink 3-2. isoflavones genistein opqr isoflavonesk 6"-o-malonylgenistin, daidzin, glycitin, %;& isoflavones äL/ Áu ã ¥¦; genistin ¸ 6"-o-acetylgenistin pqr isoflavones V, $@÷A. âÆ (vol.%), ´ Ê(rpm) ¸ ¥¦³\(oC) & É }= ©â ¥¦ (Fig. 3, 4) $¹ opqr daidzein Ê æç) _ÝA. èGl ¶[ / Ê®Ë ÿ, , k genistein, ;¦@ · Ý9, , <j@ k[ ' 7 ¶[® <j®ÃF æy( <j@F èG æy (, ] 8 pqr isoflavones B®Ä)Å o g) % 7r B, / A. , Q è pqr isoflavones $¹, 7 @÷A. æy(k Yc[ G <j@ k[ ã , @7 <j èGl ´ u <j ¸ [\ S pqr ,8SáÆ LB Y ÿ ã , A. ©â ¥¦ æç& ·k @û q, 9]t pqr) ^@] opqr ,8SáÆ d ¶& Bº;k B¼; ÙÚ) æçÝA. ã ¥¦ @÷A(Fig. 1). , o ¥¦; 80% K L; |;& f g¡ ©â ¥¦ o *+, ,-*) .÷9, :· æç ak Fig. 7 EuG7 8A. g.) ²! J Fig. 415 2003 10 615 Fig. 6. Chromatogram of isoflavones from byproduct of soybean paste Fig. 8. Chromatogram of isoflavones from byproduct of soybean paste o by preparative HPLC (80% MeOH, 25 C). by preparative HPLC (60% EtOH, 25 oC). Fig. 7. Chromatogram of isoflavones from byproduct of soybean paste Fig. 9. Chromatogram of isoflavones from byproduct of soybean paste by preparative HPLC (80% EtOH, 25 oC). by preparative HPLC (40% EtOH, 25 oC). 6k o´ EF, 6"-o-acetylgenistin, $@] K L; ý\ S isoflavones B ¥¦J,  · 4 L 89, : \ opqr isoflavones genistein ;\ du ¥¦ $¹, dÝA. Genistin! pqr isoflavones) r Z 50% [\ $%@ ] 89, isoflavones Z 97% qk a­@] 8] <jl ûÑF $ & LB) 30% [\ q, B@] opq r @7, B , u 90B [\ @F 30% ,g LBA. ¥¦;) K |; f ý\ Ø ¥¦ jkl ÝA. 80% K L; Fig. 7k o´F 60% K L; Fig. 8 g.) ; ¿, 7Q7 , S pqr isoflavones 6"-o-malonyldaidzink 6"-o-acetylgenistin, $@÷A. Fig. 9 ¥¦; ¿ 7u 40% K L; ) æçÝA. ¥¦; ¿ S isoflavones ;\ I4 êQ Fig. 8k Aw, ¥¦ isoflavones J! ð ÝA. ¥¦;) èK, KEA ¥¦j, :ë6P ; Fig. 10. Chromatogram of isoflavones from byproduct of soybean paste 75u K |;, <A.
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