Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Phenolic compounds from the flowers of Coreopsis lanceolata

큰금계국(Coreopsis lanceolata) 꽃으로부터 phenolic 화합물들의 분리 및 동정

  • Kim, Hyoung-Geun (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) ;
  • Oh, Hyun-Ji (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) ;
  • Ko, Jung-Hwan (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) ;
  • Jung, Young Sung (Department of Food Science and Biotechnology, Kyung Hee University) ;
  • Oh, Seon Min (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) ;
  • Lee, Yeong-Geun (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) ;
  • Kim, Dae-Ok (Department of Food Science and Biotechnology, Kyung Hee University) ;
  • Lee, Dae Young (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University)
  • Received : 2019.07.04
  • Accepted : 2019.09.24
  • Published : 2019.12.31
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Abstract

The flowers of Coreopsis lanceolata were extracted with 80% aqueous MeOH and the concentrates were partitioned into EtOAc, n-BuOH, and H2O fractions. The repeated silica gel (SiO2) and octadecyl silica gel column chromatographies for the EtOAc fraction led to isolation of one flavonol and one benzoyl compounds. The chemical structures of the compounds were respectively determined as melanoxetin (1) and protocatechuic acid methyl ester (2) based on spectroscopic analyses including NMR, IR, and MS. These two compounds were isolated for the first time from C. lanceolata flowers in this study. All fractions and the isolated compounds were evaluated for 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical scavenging activities.

큰금계국(Coreopsis lanceolata) 꽃을 80% MeOH 수용액으로 추출한 뒤, 감압 농축한 추출물을 EtOAc, n-butyl alcohol 및 H2O분획으로 나누었다. EtOAc 분획에 대하여 SiO2 및 ODS column chromatography를 반복실시하여 1종의 flavonol화합물과 1종의 benzoyl 화합물을 분리, 정제하였다. Nuclear magnetic resonance, infrared spectrometry 및 FAB/MS data를 해석하여, 화합물 1과 2를 각각 melanoxetin과 protocatechuic acid methyl ester으로 구조 동정 하였다. 추출물과 분획물 그리고 분리된 화합물들에 대하여 DPPH와 ABTS radical을 이용한 radical scavenging assay를 수행하였다. 이러한 결과는 큰금계국(C. lanceloata)의 꽃의 추출물, 분획물, 그리고 화합물의 높은 radical 소거활성능이 산화 스트레스로 인한 다양한 질병을 개선 할 수 있는 건강기능식품소재 개발에 좋은 후보가 될 수 있음을 시사한다.

Keywords

References

  1. Gibbs RGE (1987) List of species of southern African plants, In Memoirs of the Botanical Survey of South Africa. 2nd edition. Botanical Research Institute, Dept. of Agriculture: South Africa; 1-152(1), 1-270(2)
  2. Zheng J, Yu X, Maninder M, Xu B (2018) Total phenolics and antioxidants profiles of commonly consumed edible flowers in China. Int J Food Prop 21: 1524-1540 https://doi.org/10.1080/10942912.2018.1494195
  3. Puri B, Seshadri TR (1954) Survey of anthoxanthins. IV. Chromatographic study of yellow garden flowers and constitution of coreopsin. J Sci Ind Res 13B: 321-325
  4. Shang YF, Oidovsambuu S, Jeon JS, Nho CW, Um BH (2013) Chalcones from the flowers of Coreopsis lanceolata and their in vitro antioxidative activity. Planta Med 79: 295-300 https://doi.org/10.1055/s-0032-1328188
  5. Tanimoto S, Miyazawa M, Inoue T, Okada Y, Nomura M (2009) Chemical constituents of Coreopsis lanceolata L. and their physiological activities. J Oleo Sci 58(3): 141-146 https://doi.org/10.5650/jos.58.141
  6. Kimura Y, Hiraoka K, Kawano T, Fujioka S, Shimada A (2008) Nematicidal activities of acetylene compounds from Coreopsis lanceolata L. Z Naturforsch C 63: 843-847 https://doi.org/10.1515/znc-2008-11-1210
  7. Shao D, Zheng D, Hu R, Chen W, Chen D, Zhuo X (2013) Chemical constituents from Coreopsis lanceolata. Zhongcaoyao 44(12): 1558-1561
  8. Kim HG, Oh HJ, Ko JH, Song HS, Lee YG, Kang SC, Lee DY, Baek NI (2019) Lanceoleins A-G, hydroxychalcones, from the flowers of Coreopsis lanceolata and their chemopreventive effects against human colon cancer cells. Bioorg Chem 85: 274-281 https://doi.org/10.1016/j.bioorg.2019.01.003
  9. Kim JW, Im S, Jeong HR, Jung YS, Lee I, Kim KJ, Park SK, Kim DO (2018) Neuroprotective Effects of Korean Red Pine (Pinus densiflora) Bark Extract and Its Phenolics. J Microbiol Biotechnol 28: 679-687 https://doi.org/10.4014/jmb.1801.01053
  10. Yang XW, Huang MZ, Zhao WQ, Jin YS, Chen HS (2009) Studies on chemical constituents of Bidens bipinnata. Jiefangjun Yaoxue Xuebao 25: 283-286
  11. Xue Y, Huang Gl, Chen Y (2018) Constituents of Lithocarpus fohaiensis. Chem Nat Comp 54: 603-605 https://doi.org/10.1007/s10600-018-2423-y
  12. Kim DO, Lee CY (2004) Comprehensive Study on Vitamin C Equivalent Antioxidant Capacity (VCEAC) of Various Polyphenolics in Scavenging a Free Radical and its Structural Relationship. Crit Rev Food Sci Nutr 44: 253-273 https://doi.org/10.1080/10408690490464960
  13. Hopia A, Heinonen M (1999) Antioxidant Activity of Flavonol Aglycones and Their Glycosides in Methyl Linoleate. J Am Oil Chem Soc 76: 139-144 https://doi.org/10.1007/s11746-999-0060-0
  14. Kim DO, Lee KW, Lee HJ, Lee CY (2002) Vitamin C Equivalent Antioxidant Capacity (VCEAC) of Phenolic Phytochemicals. J Agric Food Chem 50: 3713-3717 https://doi.org/10.1021/jf020071c
  15. Ko JH, Nam YH, Joo SW, Kim HG, Lee YG, Kang TH, Baek NI (2018) Flavonoid 8-O-Glucuronides from the Aerial Parts of Malva verticillata and Their Recovery Effects on Alloxan-Induced Pancreatic Islets in Zebrafish. Molecules 23: 833 https://doi.org/10.3390/molecules23040833
  16. Toker G, Kuepeli E, Memisoglu M, Yesilada E (2004) Flavonoids with antinociceptive and anti-inflammatory activities from the leaves of Tilia argentea (silver linden). J Ethnopharmacol 95: 393-397 https://doi.org/10.1016/j.jep.2004.08.008

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