Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Study on the Synthesis of Isoquercitrin by Enzymatic Partial Hydrolysis

효소를 이용한 부분 가수분해에 의한 isoquercitrin의 합성에 관한 연구

  • Lee, Seul Bi (Department of Polymer Engineering, College of Engineering, Suwon University) ;
  • Chung, Dae-Won (Department of Polymer Engineering, College of Engineering, Suwon University)
  • 이슬비 (수원대학교 공과대학 신소재공학과) ;
  • 정대원 (수원대학교 공과대학 신소재공학과)
  • Received : 2013.11.29
  • Accepted : 2014.02.06
  • Published : 2014.04.10
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Abstract

Isoquercitrin (IQ), quercetin monoglycoside, is classified as a polyphenol, and a minute quantity of IQ is known to be present in several plants. Recently, it was reported that IQ can be prepared by the partial enzymatic hydrolysis of quercetin diglycoside (rutin, RU). In this paper, the effects of enzyme types, enzyme amounts, and substrate concentrations on the reactivity were investigated using a series of $Pecinex^{TM}$ multi-enzymes. The reaction, when a 8 ml of Ultra Clear to 1 g of RU was applied with the substrate concentration of 1% at $50^{\circ}C$, was found to be optimum, based on the reaction rate and the selectivity to IQ.

Isoquercitrin (IQ)은 폴리페놀의 일종인 quercetin (QU)의 3번 위치에 glucose가 하나 결합해 있는 배당체로서, 천연에는 미량만이 존재하고 있다. 최근 QU의 2배당체인 rutin (RU)을 기질로 사용하여 효소에 의한 부분 가수분해에 의해 IQ를 합성할 수 있다는 것이 알려졌다. 본 논문에서는, $Pecinex^{TM}$ 계열의 복합 효소를 사용하여 RU의 선택적 가수분해에 의해 IQ를 합성하는 반응에서 최적 효소를 선정하고, 효소량 및 반응물의 농도 등의 변수에 따른 반응성을 검토하였다. 그 결과, $50^{\circ}C$에서 1%의 반응물 농도로 RU 1 g 대비 8 mL의 Ultra Clear를 사용하는 것이 반응 속도 및 IQ의 선택성 측면에서 최적인 것으로 나타났다.

Keywords

References

  1. P. C. Hollman and M. B. Katan, Absorption, metabolism and health effects of dietary flavonoids in man, Biomed. Pharmacother., 51, 305-310 (1997). https://doi.org/10.1016/S0753-3322(97)88045-6
  2. E. J. Jeong and Y. J. Cha, Reduction in Residual Pesticides and Quercetin Yields in Onion Peel Extracts by Washing, J. Life Sci., 22, 1665-1671 (2012). https://doi.org/10.5352/JLS.2012.22.12.1665
  3. M. R. Hyun, Y. S. Lee, and Y. H. Park, Antioxidative Activity and Flavonoid Content of Chrysanthemum zawadskii Flowers, Kor. J. Hort. Sci. Technol., 29, 68-73 (2011).
  4. C. I. Cheigh, S. Y. Yoo, and M. S. Chung, Efficient flavonoid extraction from apple peel by subcritical water and estimation of antioxidant activity, Kor. J. Food & Nutr., 24, 458-463 (2011). https://doi.org/10.9799/ksfan.2011.24.3.458
  5. H. J. Lee and S. N. Park, Antioxidative Effect and Active Component Analysis of Quercuss alicina Blume Extracts, J. Soc. Cosmet. Sci. Korea, 37, 143-152 (2011).
  6. R. Li, C. Yuan, C. Dong, S. Shuang, and M. M. F. Choi, In Vivo Antioxidative Effect of Isoquercitrin on Cadmium-induced Oxidative Damage to Mouse Liver and Kidney, N. Schmied. Arch. Pharmacol., 383, 437-445 (2011). https://doi.org/10.1007/s00210-011-0613-2
  7. A. P. Rogerio, A. Kanashiro, C. Fontanari, E. V. da Silva, Y. M. Lucisano-Valim, E. G. Soares, and L. H. Faccioli, Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma, Inflamm. Res., 56, 402-408 (2007). https://doi.org/10.1007/s00011-007-7005-6
  8. A. Gasparotto Junior, F. M. Gasparotto, E. L. B. Lourenco, S. Crestani, M. E. A. Stefanello, M. J. Salvador, J. E. da Silva-Santos, M. C. A. Marques, and C. A. L. Kassuya, Antihypertensive effects of isoquercitrin and extracts from Tropaeolum majus L.: evidence for the inhibition of angiotensin converting enzyme, J. Ethnopharmacol., 134, 363-372 (2011). https://doi.org/10.1016/j.jep.2010.12.026
  9. H. Inaba, M. Tagashira, D. Honma, T. Kanda, Y. Kou, Y. Ohtake, and A. Amano, Identification of hop polyphenolic components which inhibit prostaglandin E2 production by gingival epithelial cells stimulated with periodontal pathogen, Biol. Pharm. Bull., 31, 527-530 (2008). https://doi.org/10.1248/bpb.31.527
  10. N. G. Amado, D. M. Cerqueira, F. S. Menezes, J. F. Mendes da Silva, M. Neto Vivaldo, and J. G. Abreu, Isoquercitrin isolated from Hyptis fasciculata reduces glioblastoma cell proliferation and changes $\beta$-catenin cellular localization, Anti Canc. Drugs, 20, 543-552 (2009). https://doi.org/10.1097/CAD.0b013e32832d1149
  11. B. L. Williams and S. H. Wender, Isolation and identification of quercetin and isoquercitrin from apricots, Prunus armeniaca, Arch. Biochem. Biophys., 43, 319-323 (1953). https://doi.org/10.1016/0003-9861(53)90127-1
  12. J. Wang, D. Lu, H. Zhao, B. Jiang, J. Wang, X. Ling, H. Chai, and P. Ouyang, Discrimination and classification of tobacco wastes by identification and quantification of polyphenols with LC-MS/MS, J. Serb. Chem. Soc., 75, 875-892 (2010). https://doi.org/10.2298/JSC091109055W
  13. R. Mauludin, R. H. Muller, and C. M. Keck, Development of an oral rutin nanocrystal formulation, Int. J. Pharm., 370, 202-209 (2009). https://doi.org/10.1016/j.ijpharm.2008.11.029
  14. J. Wang, L. L. Zhao, G. X. Sun, Y. Liang, F. A. Wu, Z. l. Chen, and S. M. Cui, A comparison of acidic and enzymatic hydrolysis of rutin, Afr. J. Biotechnol., 10, 1460-1466 (2011).
  15. L. Chebil, C. Humeau, J. Anthoni, F. Dehez, J. M. Engasser, and M. Ghoul, Solubility of flavonoids in organic solvents, J. Chem. Eng., 52, 1552-1556 (2007).
  16. H. J. You, H. J. Ahn, and G. E. Ji, Transformation of rutin to Antiproliferative quercetin-3-glucoside by Aspergillus niger, Agric. Food Chem., 58, 10886-10892 (2010). https://doi.org/10.1021/jf102871g
  17. L. Weignerova, P. Marhol, D. Gerstorferova, and V. Kren, Preparatory production of quercetin-3-$\beta$-d-glucopyranoside using alkali-tolerant thermostable $\alpha$-l-rhamnosidase from Aspergillus terreus, Bioresource Tech., 115, 222-227 (2012). https://doi.org/10.1016/j.biortech.2011.08.029
  18. H. B. Lee, E. K. Kim, S. J. Park, S. G. Bang, T. G. Kim, and D. W. Chung, Isolation and characterization of nicotiflorin obtained by enzymatic hydrolysis of two precursors in tea seed extract, J. Agric. Food Chem., 58, 4808-4813 (2010). https://doi.org/10.1021/jf9045182
  19. D. W. Chung and S. B. Lee, Novel synthesis of leucoside by enzymatic hydrolysis of tea seed extract, J. Sci. Food Agric., 93, 362-367 (2013). https://doi.org/10.1002/jsfa.5769
  20. H. B. Lee, E. K. Kim, S. J. Park, S. G. Bang, T. G. Kim, and D. W. Chung, Isolation and anti-inflammatory effect of astragalin synthesized by enzymatic hydrolysis of tea seed extract, J. Sci. Food Agric., 91, 2315-2321 (2011). https://doi.org/10.1002/jsfa.4457
  21. S. B. Lee and D. W. Chung, Reaction Optimization for Enzymatic Synthesis of Astragalin, Appl. Chem. Eng., 23, 394-398 (2012).
  22. M. H. Lee, D. Huh, D. J. Jo, G. D. Lee, and S. R. Yoon, Flavonoids Components and Functional Properties of Citrus Peel Hydrolysate, J. Korean Soc. Food Sci. Nutr., 36, 1358-1364 (2007). https://doi.org/10.3746/jkfn.2007.36.11.1358

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