한국환경농학회지 (Korean Journal of Environmental Agriculture)

  • 제37권4호
  • /
  • Pages.260-267
  • /
  • 2018
  • /
  • 1225-3537(pISSN)
  • /
  • 2233-4173(eISSN)
한국환경농학회 (The Korean Society of Environmental Agriculture)
권호 표지
DOI QR코드

DOI QR Code

UPLC-DAD-ESI(+)-QToF/MS를 이용한 국내산 두릅나무 및 음나무 순 내 페놀산 특성 비교

Comparison of Phenolic Acid from Shoots of Aralia elata and Kalopanax pictus Cultivated in Korea Using UPLC-DAD-ESI(+)-QToF/MS

  • 김영진 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 김헌웅 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 이민기 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 이선혜 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 게릴라 아사메누 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 이수지 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 이상훈 (국립농업과학원 농식품자원부 식생활영양과) ;
  • 차연수 (전북대학교 생활과학대학 식품영양학과) ;
  • 김정봉 (국립농업과학원 농식품자원부 식생활영양과)
  • Kim, Young Jin (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Kim, Heon-Woong (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Lee, Min-Ki (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Lee, Seon-Hye (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Asamenew, Gelila (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Lee, Suji (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Lee, Sang Hoon (Department of Agro-food Resources, National Institute of Agricultural Sciences) ;
  • Cha, Youn-Soo (Department of Food Science and Human Nutrition, College of Human Ecology, Chonbuk National University) ;
  • Kim, Jung Bong (Department of Agro-food Resources, National Institute of Agricultural Sciences)
  • 투고 : 2018.10.08
  • 심사 : 2018.11.12
  • 발행 : 2018.12.31
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

UPLC-DAD-ESI(+)-QToF/MS를 사용하여 국내산 두릅나무 및 음나무 순의 페놀산을 분석한 결과 두릅나무 순에서 총 13종, 음나무 순에서 총 8종의 페놀산 성분을 동정하였으며, 내부표준물질을 이용하여 이들 개별 성분을 정량하였다. 개별 페놀산 성분 구조 동정 시 모분자에 $Na^+$ 또는 $K^+$가 결합되는 특징적인 단편이온들이 관찰되어 모분자의 분자량을 쉽게 판단할 수 있었다. 전반적인 구조 동정은 선행연구 및 표준품의 UV, MS 분석 결과를 참고하여 비교하였으며, 특히 이성질체의 효율적인 동정을 위해 SIM mode 방법을 적용하였다. 따라서 두릅나무 및 음나무 순에서 10종(3,4-dihydroxybenzoic acid, 3-O-caffeoylquinic acid, caffeic acid, 4-O-caffeoylquinic acid, 5-O-p-coumaroylquinic acid, 5-O-feruloylquinic acid, 5-O-caffeoylquinic acid methyl ester, 4,5-di-O-caffeoylquinic acid, 3-O-feruloyl-5-O-caffeoylquinic acid, 3-O-caffeoyl-5-O-feruloylquinic acid)의 페놀산이 처음으로 확인되었다. 총 페놀산 함량은 두릅나무 순, 음나무 순이 각각 754.8, 845.3 mg/100g으로 확인하였다. 주요 성분인 5-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid는 두릅나무 순에서 각각 총 페놀산 함량 중 49, 44%로 서로 비슷한 함량을 보인 것이 비해 음나무 순에서는 각각 91, 3%로 확인되었다. 따라서 음나무 순에 비해 두릅나무 순에서 dicaffeoylquinic acid류의 생합성이 활발하게 이루어졌다는 것을 짐작할 수 있었으며, 본 연구 결과는 이들의 생합성에 관여하는 효소, 유전 인자 등을 규명하는데 중요한 기초 자료로 활용될 것으로 사료된다.

BACKGROUND: In this study, shoots of Aralia elata and Kalopanax pictus which belong to the Araliaceae family were analyzed using UPLC-DAD-ESI(+)-QToF/MS to characterize of individual phenolic acids. METHODS AND RESULTS: Total thirteen phenolic acids were identified, and nine hydroxycinnamic acid derivatives have been identified for the first time in shoots of Aralia elata and Kalopanax pictus. For total phenolic acid content (mg/100g dry weight), shoots of Aralia elata and Kalopanax pictus showed 754.8 and 845.3 mg/100g, respectively. 5-O-Caffeoylquinic acid (49%) and 3,5-di-O-caffeoylquinic acid (44%) were found as major phenolic acids in Aralia elata, while 5-O-caffeoylquinic acid (91%) was a major component in Kalopanax pictus. CONCLUSION: On comparing the two plants, it was considered that the biosynthesis of 3,5-di-O-caffeoylquinic acid can be affected by 5-O-caffeoylquinic acid in Aralia elata.

키워드

참고문헌

  1. Clifford, M. N., Jaganath, I. B., Ludwig, I. A., & Crozier, A. (2017). Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity. Natural Product Reports, 34(12), 1391-1421. https://doi.org/10.1039/C7NP00030H
  2. Clifford, M. N., Knight, S., Surucu, B., & Kuhnert, N. (2006). Characterization by LC-$MS^n$ of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids. Journal of Agricultural and Food Chemistry, 54(6), 1957-1969. https://doi.org/10.1021/jf0601665
  3. Crozier, A., Jaganath, I. B., & Clifford, M. N. (2009). Dietary phenolics: chemistry, bioavailability and effects on health. Natural Product Reports, 26(8), 1001-1043. https://doi.org/10.1039/b802662a
  4. Heleno, S. A., Martins, A., Queiroz, M. J. R., & Ferreira, I. C. (2015). Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chemistry, 173, 501-513. https://doi.org/10.1016/j.foodchem.2014.10.057
  5. Hu, W., Huang, C., & Wang, M. H. (2012). Chemical composition, nutritional value, and antioxidant constituents of Kalopanax pictus leaves. Food Chemistry, 131(2), 449-455. https://doi.org/10.1016/j.foodchem.2011.09.005
  6. Hwang, I. Y., Hwang, S. A., & Jeong, C. S. (2013). Effects of Kalopanax pictus extracts and their related origin on gastric lesions. Journal of Food Hygiene and Safety, 28(4), 367-375. https://doi.org/10.13103/JFHS.2013.28.4.367
  7. Jaiswal, R., Sovdat, T., Vivan, F., & Kuhnert, N. (2010). Profiling and characterization by LC-$MS^n$ of the chlorogenic acids and hydroxycinnamoylshikimate esters in mate (Ilex paraguariensis). Journal of Agricultural and Food Chemistry, 58(9), 5471-5484. https://doi.org/10.1021/jf904537z
  8. Jin, U. H., Lee, J. Y., Kang, S. K., Kim, J. K., Park, W. H., Kim, J. G., Moon, S. K., & Kim, C. H. (2005). A phenolic compound, 5-caffeoylquinic acid (chlorogenic acid), is a new type and strong matrix metalloproteinase-9 inhibitor: isolation and identification from methanol extract of Euonymus alatus. Life Sciences, 77(22), 2760-2769. https://doi.org/10.1016/j.lfs.2005.02.028
  9. Kang, Y. S., Cho, T. O., & Hong, J. S. (2009). Quality characteristics of sulgidduk containing added Aralia elata leaf powder. Korea Society of Food & Cookery Science, 25(5), 593-599.
  10. Kim, E. J., & Lee, W. J. (2012). Quality characteristics of noodles containing shoots and leaves of Aralia elata and Kalopanax pictus. Journal of the Korean Society of Food Science and Nutrition, 41(4), 571-575. https://doi.org/10.3746/jkfn.2012.41.4.571
  11. Kim, W. J. (2015). Development for customer oriented food products and marketing strategy in small businesses. Food Industry and Nutrition, 20(1), 8-10.
  12. Kim, Y. H., Kim, J. P., Yun, B. S., Moon, S. S., & Yoo, I. D. (1998) Antioxidants isolated from Kalopanax pictus. Korean Journal of Medicinal Crop Science, 11, 89-109.
  13. Kwon, B. S., Park, S. K., Kim, J. M., Kang, J. Y., Park, S. H., Kang, J. E., Lee, C. J., Park, S. B., Yoo, S. K., Lee, U., & Heo, H. J. (2018). Antioxidant capacity and hepatoprotective effect of ethyl acetate fraction from shoot of Aralia elata on alcohol-induced cytotoxicity. Korean Journal of Food Science and Technology, 50(2), 216-224. https://doi.org/10.9721/KJFST.2018.50.2.216
  14. Lee, E. B., Hyun, J. E., Kim, I. H., & Whang, W. K. (2001). Anti-inflammatory activity of methanol extract of Kalopanax pictus bark and its fractions. Journal of Ethnopharmacology, 77(2-3), 197-201. https://doi.org/10.1016/S0378-8741(01)00301-4
  15. Liang, N., & Kitts, D. (2015). Role of chlorogenic acids in controlling oxidative and inflammatory stress conditions. Nutrients, 8(1), 16. https://doi.org/10.3390/nu8010016
  16. Ma, S. J., Ko, B. S., & Park, K. H. (1995). Isolation of 3,4-dihydroxybenzoic acid with antimicrobial activity from bark of Aralia elata. Korean Journal of Food Science and Technology, 27(5), 807-812.
  17. Ma, S. J., Kuk, J. H., Ko, B. S., & Park, K. H. (1996). Isolation and characterization of 4-hydroxycinnamic acid with antimicrobial activity from Aralia elata. Agricultural Chemistry and Biotechnology, 39(4), 265-267.
  18. Mattila, P., & Hellstrom, J. (2007). Phenolic acids in potatoes, vegetables, and some of their products. Journal of Food Composition and Analysis, 20(3-4), 152-160. https://doi.org/10.1016/j.jfca.2006.05.007
  19. Menin, B., Comino, C., Moglia, A., Dolzhenko, Y., Partis, E., & Lanteri, S. (2010). Identification and mapping of genes related to caffeoylquinic acid synthesis in Cynara cardunculus L. Plant Science, 179(4), 338-347. https://doi.org/10.1016/j.plantsci.2010.06.010
  20. Nugroho, A., Kim, M. H., Lee, J. H., Kim, J. D., Lee, K. R., Choi, J. S., Yoo, Y. M. & Park, H. J. (2011) Polyphenol analysis and peroxynitrite scavenging effect of the extracts from eight Korean mountainous vegetable. The Korean Society of Pharmacognosy, 42(1), 38-45.
  21. Oh, I. S., Han, J. W., & Kim, H. G. (2005). Water extracts of Aralia elata root bark enhances migration and matrix metalloproteinases secretion in porcine coronary artery endothelial cells. Biotechnology and Bioprocess Engineering, 10(4), 372-377. https://doi.org/10.1007/BF02931858
  22. Quang, T. H., Ngan, N. T. T., Minh, C. V., Kiem, P. V., Nhiem, N. X., Tai, B. H., Thao, N. P., Luyen, B. T. T., Song, S. B., & Kim, Y. H. (2011). Anti-inflammatory and PPAR subtypes transactivational activities of phenolics and lignans from the stem bark of Kalopanax pictus. Bulletin of the Korean Chemical Society, 32(11), 4049-4054. https://doi.org/10.5012/bkcs.2011.32.11.4049
  23. Rice-Evans, C., Miller, N., & Paganga, G. (1997). Antioxidant properties of phenolic compounds. Trends in Plant Science, 2(4), 152-159. https://doi.org/10.1016/S1360-1385(97)01018-2
  24. Sano, K., Sanada, S., Ida, Y., & Shoji, J. (1991). Studies on the constituents of the bark of Kalopanax pictus Nakai. Chemical and Pharmaceutical Bulletin, 39(4), 865-870. https://doi.org/10.1248/cpb.39.865
  25. Sato, Y., Itagaki, S., Kurokawa, T., Ogura, J., Kobayashi, M., Hirano, T., Sugawara, M., & Iseki, K. (2011). In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. International Journal of Pharmaceutics, 403(1-2), 136-138. https://doi.org/10.1016/j.ijpharm.2010.09.035
  26. Viacava, G. E., Roura, S. I., Berrueta, L. A., Iriondo, C., Gallo, B., & Alonso-Salces, R. M. (2017). Characterization of phenolic compounds in green and red oak-leaf lettuce cultivars by UHPLC-DAD-ESI-QToF/MS using MSE scan mode. Journal of Mass Spectrometry, 52(12), 873-902. https://doi.org/10.1002/jms.4021
  27. Zhao, Y., Wang, J., Ballevre, O., Luo, H., & Zhang, W. (2012). Antihypertensive effects and mechanisms of chlorogenic acids. Hypertension Research, 35(4), 370-374. https://doi.org/10.1038/hr.2011.195
  28. Zheng, W., & Clifford, M. N. (2008). Profiling the chlorogenic acids of sweet potato (Ipomoea batatas) from China. Food Chemistry, 106(1), 147-152. https://doi.org/10.1016/j.foodchem.2007.05.053