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1 Printed in the Republic of Korea ANALYTICAL SCIENCE & TECHNOLOGY Vol. 29, No. 4, , Note ( 단신 ) Development of HPLC-UV method for detection and quantification of seven organic acids in animal feed Jin kug Kim, Mi Jin Lee, Ye Ji Lee, Hye Jin Kim, Min Hee Jeong and Ho Jin Kim National Agricultural Products Quality Management Service, Kimchun , Korea (Received June 2, 2016; Revised June 30, 2016; Accepted August 24, 2016) 사료중유기산 7 종동시분석법개발및유통사료의모니터링 김진국ㆍ이미진ㆍ이예지ㆍ김혜진ㆍ정민희ㆍ김호진 국립농산물품질관리원시험연구소 ( 접수, 수정, 승인 ) Abstract: A novel and simple method for detecting seven organic acids (formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid and propionic acid) in animal feed using high performance liquid chromatography equipped with a photo-diode array detector (HPLC/PDA) was developed. The chromatographic peaks of the seven organic acids were successfully identified by comparing their retention times and UV spectra with reference standards. Method validation was performed in terms of linearity, sensitivity, selectivity, accuracy, and precision. The limits of detection (LODs) for the instrument employed in these experiments ranged from 12 to 8,026 µg/kg, and the limits of quantification (LOQs) ranged from 43 to 26,755 µg/kg. Average recoveries of the seven organic acids ranged from 79.3 to 95.2 %. Method replication resulted in intra- day and interday peak area variation of <3.2 %. The developed method was specific and reliable and is therefore suitable for the routine analysis of organic acids in animal feed. 요약 : 본연구에서는사료첨가제로이용되고있는유기산 7종 (formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid, propionic acid) 의동시분석법개발을위한연구를실시하였다. 7 종의화합물은표준물질의 Retention time과 UV spectra를통해구별하였고, 분석법검증은직선성, 민감성, 선택성, 정확성, 정밀성을통하여검증하였다. 그결과로 LOD와 LOQ의범위가각각 43~26,755 µg/kg, 12-8,026 µg/kg 으로설정하였고, 평균회수율이 79.3~95.2 % 로우수하게보였으며, intra-day, inter-day 에대한전반적인상대표준편차 (%RSD) 는 3.2 % 미만으로나타났다. 이와같이검증된자료를통해유기산의동시분석에대한직선성, 민감성, 선택성, 정확성및정밀성을확인하였고, 높은수준을나타냄을알수있었다. 이를바탕으로유기산이검출되는단미사료 46 가지를분석에적용하여진행하였고, 정량과동시분석검출을위한방법은 RP-HPLC/UV 검출기를이용하여성공적으로개발되었다. 따라서본연구결과를바탕으로하여사료중의유기산의분석이신속하고정확해졌을뿐아니라, 다른종류의사료또한이를적용하여효율적으로이용할수있을것으로판단된다. Key words: organic acid (formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid, propionic acid), animal feed, hplc, simultaneous Corresponding author Phone : +82-(0) Fax : +82-(0) rex7878@korea.kr This is an open access article distributed under the terms of the Creative Commons Attribution Non-Commercial License ( org/licenses/ by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. 202
2 Development of HPLC-UV method for detection and quantification of seven organic acids in animal feed 서론 사료첨가제로이용되고있는유기산은 acetic acid, citric acid, formic acid, fumaric acid, lactic acid, propionic acid 등으로개별적으로사료와음수에첨가하거나복합유기산제형태로이용되고있다. 1 사료중에유기산을첨가하면가축의위장관의 ph를조정해항균, 항곰팡이작용으로독소생성을감소시키고유산균, 효모등의서식을유리하게만들어성장촉진과영양소이용률개선에도움을준다. 또한위산의 ph를낮춰펩신활성화를증가시켜단백질과식물성사료의소화율개선에도움을주며, 1-5 citric acid 및 fumaric acid은대사과정 (TCA Cycle) 의중간대사물질로에너지공급효과가있다. 6 이러한유기산의기능으로세계적으로동물용사료내항생제를대체하는원료로인정받고있다. 유기산을먹이면영양소이용률이성장촉진용항생제첨가시와유기산첨가시유사한경향을보인다는연구결과가보도되고있다. 7,8 이러한작용으로동물용사료, 사일리지및곡물의보존제로폭넓게사용되고있다. 유기산은종류가다양하고그종류에따라유해균을억제하는작용기전과억제균의종류가달라사료로사용할경우혼합하여복합유기산제를많이사용하는데, 1 현재의사료공정서상의분석법은적정법 9 으로실험자간오차가크고, 한번에한성분만분석할수있어분석능률이떨어지며, 사료검정업무물량증가로시간이오래걸려현실적으로적합하지않다. 따라서유기산 (formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid, propionic acid) 의물리화학적특성을파악하고사료에서의분리능을확보하여 HPLC를이용한동시분석법개발로신속, 정확한분석법활용으로업무의효율화가필요하다. 유기산의분석방법으로는 HPLC-UV(high performance liquid chromatography-ultraviolet detection), LC-MS/MS(liquid chromatography-mass spectrometry/ mass spectrometry), 15 GC(gas chromatography) 16,17 등으로다양하게보고되고있다. LC-MS/MS는분자량과화합물의구조적특성에대한정보를제공하므로분리, 정량적인측면에서다른분석방법에비해유용하지만이는고가의장비일뿐아니라조작이어렵고보편화되어있지않아적용하는데어려움이있다. 다른많은연구들은보다가격이저렴하고, 조작이편리하며, 보편화되어있는 HPLC-UV 검출방법을선호 하고있어, 유기산을분석하는데적합한방법이라고판단되었다. 본연구에서는단미사료에서 7개 (formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid, propionic acid) 의유기산을동시분석하였고, 이는신속하고정확한분석으로분석업무의효율성을높일뿐아니라사료의표준품관리에도움으로작용하고자하였다 시료 2. 재료및방법 단미사료에포함된유기산을대상으로실험하였으며, 시료는지역자치단체 ( 서울, 경기, 강원, 대전, 충북, 충남, 전북, 전남 ; 2015년 ) 에서의뢰받은단미사료를사용하였다. 총 46 개의시료를사용하였으며, 시료는분말로분쇄하여사용하였다 (HMF-100; HANIL Electric Co., Seoul, Korea). 분쇄기의속도는 22,000 rpm으로설정하고, 크기는 400~1000 µm으로분쇄하였다. 모든시료는 4 o C에저장하였다 시약 HPLC급시약으로 HCl, H 2 SO 4 는 Merck (Darmstadt, Germany) 에서구입하였다. 증류수는 Milli-Q RiOsTM/ Elix water purification system (Millipore, Bedford, MA, USA) 을사용하였다. Malic acid (99 %), lactic acid (98 %), acetic acid (99 %), citric acid (99.9 %), fumaric acid (98 %) 표준품은 Sigma-Aldrich에서구입하였고, Formic acid (98 %), Propionic acid (99.8 %) 은 Fluka에서구입하였다. 본시험에사용된유기산의물리화학적특성은 Table 1에나타내었다 표준품전처리 표준물질인 Formic acid, Malic acid, Lactic acid, Acetic acid, Citric acid, Fumaric acid, Propionic acid 를 0.4 % 염산용액에녹여 1,000 mg/l의농도로조제된 stock solution을 1.0, 5.0, 10.0, 50.0, mg/l의농도가되도록 working solution을조제하였다. 그후 10 µl씩기기에주입하여나타난크로마토그램상의 peak 면적을기준으로표준검량선을작성하였다 시료전처리 1 g의균질화된시료를 tube에칭량하고, 0.4 % HCl 20 ml를주사하여혼합한다. 그혼합물을초음파추 Vol. 29, No. 4, 2016
3 204 Jin kug Kim, Mi Jin Lee, Ye Ji Lee, Hye Jin Kim, Min Hee Jeong and Ho Jin Kim Table 1. Physicochemical properties of formic acid, malic acid, lactic acid, acetic acid, citric acid, fumaric acid, propionic acid Common name Chemical structure Chemical formula Melting point Boiling point Solubility in water Formic acid CH 2 O o C o C miscible Malic acid C 4 H 6 O o C (266 o F; 403 K) Lactic acid C 3 H 6 O 3 D : 53 o C L: 53 o C D/L: 16.8 o C Acetic acid C 2 H 4 O 2 61 to 62 o F; 16 to 17 o C; 289 to 290 K Citric acid C 6 H 8 O o C (313 o F; 429 K) Fumaric acid C 4 H 4 O 4 (549 o F; 560 K) 287 o C (decomp) Propionic acid C 3 H 6 O o C (-4.9 o F; K) 122 o C (252 o F; 395 K) 12 mmhg 118 to 119 o C; 244 to 246 o F; 391 to 392 K 310 o C (590 o F; 583 K) decomposes from 175 o C o C ( o F; K) 558 g/l (at 20 o C) miscible g/100 ml (10 o C) g/100 ml (20 o C) g/100 ml (30 o C) g/100 ml (40 o C) g/100 ml (80 o C g/100 ml (100 o C) 4.3 g/l at 20 o C 8.19 g/g (-28.3 o C) g/g (-23.9 o C) Miscible ( o C) 출기를이용하여 20분간추출한다음 0.4 % 염산용액으로정용하여원심분리 (3000 rpm, 10 min, 4 o C) 를진행한후, 필터 (0.45 µm) 한다 HPLC 분석조건 분석에사용된 HPLC는 auto sampler, photodiode array detector (PDA) 가장착된 Shiseido Nanospace SI-2 system (Shiseido, Tokyo, Japan) 에서진행하였고, EZ Chrom Elite software (Aglient) 을이용하였다. 컬럼은역상 Imtakt Unison UK-C18 ( mm, 3 µm particle size) (Tokyo, Japan) 을사용하여모든분리를진행하였으며, 온도는 40 o C로설정하였다. 이동상은유기산의분리능개선과 ph를낮추기위해 H 2 SO 4 를첨가하여 20 mm H 2 SO 4 를이동상조건으로설정하였다. 시료는 10 µl를주입하였고, 유속은 0.8 ml/min으로설정하였으며, 모든피크는 210 nm의파장을이용하여검출하였다. 이동상은사용하기전에 0.45 µm 필터 (Millipore, Milford, MA, USA) 를통해여과하고, 진공하에탈기하여사용하였다. Table 2. Retention time, Resolution, Asymmetry of seven organic acid compound Compound 2.6. 분석법검정 Retention time(min) Resolution Asymmetry Formic acid Malic acid Lactic acid Acetic acid Citric acid Fumaric acid Propionic acid 분석법의검증은 International Conference on Harmonization (ICH, 2005) 18 와 International Union of Pure and Applied Chemistry(IUPAC, 2002) 19 에서설정한기준을근거로직선성 (linearity), 민감성 (sensitivity), 선택성 (selectivity), 정확성 (accuracy), 정밀성등으로실시하였다 (Table 2~4). Analytical Science & Technology
4 Development of HPLC-UV method for detection and quantification of seven organic acids in animal feed 205 Table 3. Linear equation of calibration curve for the quantification, limit of detection and limit of quantification of seven organic acid compound Compound Slope Linear equation Intercept R Y LOD (μg/kg) LOQ (μg/kg) Formic acid e Malic acid e Lactic acid e Acetic acid e X e Citric acid e ,026 26,755 Fumaric acid Propionic acid e e ,988 13,296 Table 4. Precision, Recovery of seven organic acid compound Compound Precisions (%RSD) Intra -day Inter -day Recovery Low level High level (2.0 mg/kg) (20.0 mg/kg) Formic acid Malic acid Lactic acid Acetic acid Citric acid Fumaric acid Propionic acid 결과및고찰 3.1. 분석법검정개발된 RP-HPLC/UV 분석방법은단미사료에서유기산의분석에대한조건을충족하는지확인하기위하여유효성검증을진행하였고, 이는직선성 (linearity), 민감성 (sensitivity), 선택성 (selectivity), 정확성 (accuracy) 및정밀성 (precision) 을통해검증하였다. 선택성 (selectivity) 은크로마토그래프상에서피크의간섭유무에의해결정되고, 이는특정정량파장 (210 nm) 에서빈크로마토그램을사용하여측정하였다. Fig. 1과 Table 2에서관찰되어지듯이, 7 개의유기산 Fig. 1. HPLC Chromatogram for standard. Vol. 29, No. 4, 2016
5 206 Jin kug Kim, Mi Jin Lee, Ye Ji Lee, Hye Jin Kim, Min Hee Jeong and Ho Jin Kim Table 5. Determination of the content (g/kg) of seven compounds in feed using the proposed method Sample Formic acid Malic acid Lactic acid Acetic acid Citric acid Fumaric acid Propionic acid Analytical Science & Technology
6 Development of HPLC-UV method for detection and quantification of seven organic acids in animal feed 207 의 Retention time을살펴보면 16분이전에모든피크가나타나고, 7 개의화합물이모두성공적으로분리됨을알수있었다. 또한 Resolution과 Asymmetry가각각 4.9~15.7, 0.86~1.30으로나타나 HPLC 시스템에대한선택성이양호함을확인하였다. 직선성 (linearity) 은 working solution을사용하여각화합물에대한외부검량선을작성함으로써평가하였다. 검량선은일곱개의각기다른농도와분석피크면적을설정하여작성하였고, 혼합표준용액의각농도는 3 반복으로주입한후, 회귀매개변수를계산하였다. 그결과는상관계수 (R 2 ) 가 이상으로나타나높은직선성을확인할수있었으며 (Table 3), 이러한결과는외부표준검량선의정량목적을위해적용될수있음을보여준다. 민감성 (sensitivity) 은검출한계 (LOD) 와정량한계 (LOQ) 값을결정함으로써평가하였고, 이값은신호대잡음비 (S/N비) 의각각의회귀방정식에서반응및기울기를바탕으로산출하였다. 검출한계는분석기기 의최적분석조건하에서 S/N비의 3:1로써, 3 배에해당하는성분의피크로하였다. 또한분석기기의정량한계 (LOQ) 는목적성분의유무가정확히판단될수있는최저농도로, S/N비가 10:1로써, 10 배에범위에해당하는양이며, 본실험에서는 LOD의 3배를적용하였다. 검출한계의경우, 43~26,755 µg/kg으로값의범위를설정하였고, 정량한계는 12~8,026 µg/kg으로설정하였다 (Table 3). 정밀성 (precision) 은 intra-, inter- day의정밀성을측정함으로써결정하였다. intra-day의정밀성은용액을 3일연속으로관찰하면서하루동안혼합표준용액을 6회반복하여분석한결과이고, 이는상대표준편차 (%RSD) 의백분율로써산출하였다. intra-day에대한전반적인 %RSD는 3.1 % 미만이었고, 반면에 interday에대한 %RSD의값은 3.2 % 미만으로나타났다 (Table 4). 정확성 (accuracy) 은 AAFOCO(Association of American Feed Control Official, Swine Mineral and Vitamin Supplement) 시료에다른농도 (high: 20.0 mg/kg and low: 2.0 mg/kg) 의혼합표준용액을첨가함으로써평가하였으며, 그혼합물은개발된 HPLC 방법을사용하여추출하였다. 모든실험은 3 반복하여진행하였고, Table 4에서설명한바와같이 79.3~95.2 % 의우수한회수율을보였으며, 이방법에대한정확성은높은수준으로나타남을알수있었다. 이와같이검증된자료를바탕으로한이방법은유기산의동시분석에대 한직선성, 민감성, 선택성, 정확성및정밀성을제공하기위함이다 단미사료중유기산의함량본연구에서는유기산이검출되는단미사료 46 가지를가지고분석을진행하였으며, 단미사료는지역자치단체 ( 서울, 경기, 강원, 대전, 충북, 충남, 전북, 전남 ) 에서의뢰받은시료를사용하였다. 각시료는 3 반복으로실험을진행하였으며, 7 개의화합물은표준물질의 Retention time과 UV spectra를통해구별하였다. 단미사료에서 7가지유기산화합물의정성및정량의조성은상당히다양하다. 더구체적으로살펴보면, formic acid의함량의범위가 3.18~44.22 g/kg이고, 평균함량이 g/kg이며, malic acid의함량의값의범위와평균이각각 1.53~61.59 g/kg, g/kg으로나타남을알수있었다. 또한 lactic acid와 acetic acid 의함량 ( 평균 ) 이각각 1.42~88.85 g/kg (27.27 g/kg), 0.21~56.01 g/kg (23.33 g/kg) 로확인되었으며, citric acid의경우 1.61~74.31 g/kg으로함량의범위와 g/ kg을평균으로알수있었다. fumaric acid는 13.09~ g/kg의함량과평균 g/kg을확인하였으며, propionic acid의함량 ( 평균 ) 은 2.77~44.62 g/kg (19.42 g/kg) 으로나타났다. 따라서단미사료로부터 7개의유기산의정량과동시분석검출을위한시료, 정성및정량적방법은 RP- HPLC/UV 검출기를이용하여성공적으로개발되었다. 또한이러한방법은정확성과정밀성을보여다른종류의사료또한이를적용하여효율적으로이용할수있을것이라판단된다. 결과적으로본연구를통한이 HPLC 방법은특이성, 민감성등으로인하여일상적인분석을위한좋은대안을제공하고, 단미사료의안정적인품질평가방법으로써적용될수있을것으로사료된다. References 1. D. W. Kim, J. H. Kim, S. K. Kim, G. H. Kang, H. K. Kang, S. J. Lee and S. H. Kim, J. Anim. Sci. Technol., 51, (2009). 2. J. W. Joo, J. Y. Choi, S. C. Choi, W. T. Cho, B. J. Chae and Y. X. Yang, J. Anim. Sci. Technol., 51, (2009). 3. K. H. Partanen and Z. Mro, Nutr. Res. Rev., 12, (1991). 4. I. H. Hwang, Feed Industry, 2, (2004). Vol. 29, No. 4, 2016
7 208 Jin kug Kim, Mi Jin Lee, Ye Ji Lee, Hye Jin Kim, Min Hee Jeong and Ho Jin Kim 5. H. K. Yoon, Y. H. Kim and J. H. Han, Korean J. Vet. Serv., 32(1), (2009). 6. X. Yin, Jianghua Li, H. D. Shin, Guocheng Pu, Long Liu and Jian Chen, Biotechnol. Adv., 33, (2015). 7. C. H. Lee, I. H. Jo, J. C. Shon and S. H. Lee, Korean J. Org. Agric., 17, (2009). 8. Sung Su Ill, Ministry for Food, Agriculture, Forestry and Flsheries (MIFAFF), (2009). 9. Standard and specification for animal feeds, Ministry of Agriculture. Food and Rural Affairs (MAFRA), ( ). 10. Rodrigo Scherer, Ana Cecilia Poloni Rybka, Cristiano Augusto Ballus, Adriana Dillenburg Meinhart, Jose Teixeira Filho, Helena Teixeira Godoy, Food Chem., 135, (2012). 11. Hans A. Eyeghe-Bickong, Erik O. Alexandersson1, Liezel M. Gouws, Philip R. Young and Melane A. Vivier, J. Chromatogr. B, , (2012). 12. Giuseppe Zeppa, Lorenza Conterno and Vincenzo Gerbi, Agric. Food Chem., 59, (2001). 13. Jorge Bouzas, Carlos A. Kantt, Floud Bodyfelt and J. Antonio, Torres, Food Sci., 56, (1991). 14. Fabio Chinnici, Umberto Spinabelli, Claudio Riponi and Aureliano Amati, J. Feed Compos. Anal., 18, (2005). 15. X.-Q. Wang, F.-Y. Wei, Z.-F. Wei, L. Zhang, M. Luo, Y.-H. Zhang, Y.-G. Zu and Y.-J. Fu, Sep. Purif. Technol., 35, (2014). 16. Ute Roessner, Cornelia Wagner, Joachim Kopka, Richard N. Trethewey and Lothar Willmitzer, Plant J., 23, (2000). 17. M.-H. Yanga and Y.-M. Choongb, Food Chem., 75, (2001). 18. ICH International Conference Harmonization, Validation of analytical procedures: test and methodology (2005). 19. M. Thompson, S. L. R. Ellison and R. Wood, Int. Union Pure Appl. Chem.(IUPAC), 74, (2002). Analytical Science & Technology
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