DOI QR코드

DOI QR Code

Phenolic Compounds from Japanese Anise (Illicium anisatum L.) Leaves

  • Shinn, Seong-whan (Department of Advanced Materials and Chmemical Engineering, Halla university) ;
  • Min, Hee-Jeong (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Bae, Young-Soo (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University)
  • Received : 2018.08.16
  • Accepted : 2018.11.19
  • Published : 2019.01.25

Abstract

Japanese anise (Illicium anisatum L.) leaves were collected and ground after drying, then immersed with 50 % aqueous acetone for 3 days. After filtration, the extracts were fractionated with n-hexane, chloroform ($CHCl_3$), ethylacetate (EtOAc) and $H_2O$, and then freeze dried after concentration. A portion of EtOAc (3.12 g) and $H_2O$ (6.08 g) soluble fractions were chromatographed on a Sephadex LH-20 column with various aqueous MeOH solution to isolate the compounds. Compound 1 ((+)-catechin) was isolated from EtOAc soluble fraction. Compounds 2 (quercetin), 3 (quercitrin) and 4 (2''-O-rhamnosylvitexin) were isolated from $H_2O$ soluble fraction. For the first time, quercitrin (3) and 2''-O-rhamnosylvitexin (4) of the isolated compounds were obtained from the extracts of japanese anise leaves.

Keywords

HMJGBP_2019_v47n1_1_f0001.png 이미지

Fig. 1. Chemical structures of isolated compounds.

HMJGBP_2019_v47n1_1_f0002.png 이미지

Fig. 2. Selected HMBC correlations observed in compound 4.

References

  1. Foo, L.Y., McGraw, G.W., Hemingway, R.W. 1983. Condensed tannins: Preferential substitution at the interflavanoid bond by sulphite ion. Journal of the Chemical Society, Chemical Communications 12: 672-673.
  2. Jeong, M.J., Yang, J.Y., Choi, W.S., Kim, J.W., Kim, S.J., Park, M.J. 2017. Chemical Compositions and Antioxidant Activities of Essential Oil Extracted from Neolitsea aciculata (Blume) Koidz Leaves. Journal of the Korean Wood Science and Technology 45(1): 96-106. https://doi.org/10.5658/WOOD.2017.45.1.96
  3. Jung, J.Y., Ha, S.Y., Yang, J.k. 2017. Response Surface Optimization of Phenolic Compounds Extraction From Steam Exploded Oak Wood (Quercus mongolica). Journal of the Korean Wood Science and Technology 45(6): 809-827. https://doi.org/10.5658/WOOD.2017.45.6.809
  4. Kassem, M., Mosharrafa, S.A., Saleh, N.A.M., Abdel-Wahab, S.M. 2000. Two new flavonoids from Retama raetam. Fitoterapia 71: 649-654. https://doi.org/10.1016/S0367-326X(00)00224-0
  5. Kim, H.Y., Kang, M.H. 2005. Screening of Korean medicinal plants for lipase inhibitory activity. Phytotherapy Research 19: 359-361. https://doi.org/10.1002/ptr.1592
  6. Kim, H.Y., Kim, K. 2003. Protein glycation inhibitory and antioxidative activities of some plant extracts in vitro. Journal of Agricultural and Food Chemistry 51: 1586-1591. https://doi.org/10.1021/jf020850t
  7. Kim, H.Y., Oh, J.H. 1999. Screening of Korean forest plants for rat lens aldose reductase inhibition. Bioscience, Biotechnology and Biochemistry 63: 184-188. https://doi.org/10.1271/bbb.63.184
  8. Kim, J.K., Park, W.G., Bae, Y.S. 1997. Flavonoid glycosides from needles of Larix leptolepis (Pinaceae). Journal of the Korean Wood Science and Technology 25(2): 81-87.
  9. Kim, J.W., Choi, W.S., Lee, S.S., Park, M.J. 2015. Comparative Study on The Composition of Essential Oil by Supercritical Carbon Dioxide Extraction and Hydro-distillation from Chamaecyparis obtusa Leaves. Journal of the Korean Wood Science and Technology 43(4): 494-503. https://doi.org/10.5658/WOOD.2015.43.4.494
  10. Kim, J.Y., Kim, S.S., Oh, T.H., Baik, J.S, Song, G.P., Lee N.H., Hyun, C.G. 2009. Chemical composition, antioxidant, anti-elastase, and anti-inflammatory activities of Illicium anisatum essential oil. Acta Pharmaceutica 59: 289-300. https://doi.org/10.2478/v10007-009-0022-y
  11. Kwon, D.J. 2005. Antioxidative activities on the extractives of Larix kaempfer Carr. needles. Master Disseration submitted to Kangwon National University, South Korea.
  12. Kwon, D.J., Kim, J.K., Ham, Y.H., Bae, Y.S. 2007. Flavone glycosides from the aerial parts of Lespedza cuneata G. Don. Journal of Applied Biological Chemistry 50(4): 344-347.
  13. Lee, J.H., Chung, H.K., Baek, N. I., Kim, S.H., Hee, W.P., Dae, K.K. 2004. Phytochemical constituents from Diodia teres. Archives of Pharmacal Research 27(1): 40-43. https://doi.org/10.1007/BF02980043
  14. Lee, T.S., Min, H.J., Bae, Y.S. 2015. Phenolic Glycosides from Cercidiphyllum japonicum Leaves. Journal of the Korean Wood Science and Technology 43(5): 591-599. https://doi.org/10.5658/WOOD.2015.43.5.591
  15. Lee, T.S., Ryu, W.G., Bae, Y.S. 2015. ${\alpha}$-Glucosidase Inhibition Activity of the Extracts of Katsura Tree (Cercidiphyllum japonicum Sieb. Et Zucc) Leaves. Journal of the Korean Wood Science and Technology 43(2): 238-247. https://doi.org/10.5658/WOOD.2015.43.2.238
  16. Lew, J.H., Kwak, J.H., Lee, K.R., Zee, O.P. 1998. Flavonoids from Kylinga brevifolia var. leiolepsis. Korean Journal of Pharmacognosy 29(2): 71-74.
  17. Luo, W., Zhao, M., Yang, B., Shen, G. and Rao, G. 2009. Identification of bioactive compounds in Phyllenthus emblica L. fruit and their free radical scavenging activities. Food Chemistry 114(2): 499-504. https://doi.org/10.1016/j.foodchem.2008.09.077
  18. Min, H.J., Bae, Y.S. 2017. Phenolic compounds from Japanese anise (Illcium anisatum L.) twigs. Journal of the Korean Wood Science and Technology 45(4): 456-462. https://doi.org/10.5658/WOOD.2017.45.4.456
  19. Owen, R.W., Haubner, R., Mier, W., Giacosa, A., Hull, W.E., Spiegelhalder, B., Bartsch, H. 2003. Isolation, structure eelucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. Food and Chemical Toxicology 41: 703-717. https://doi.org/10.1016/S0278-6915(03)00011-5
  20. Pyo, M.K., Koo, Y.K., Yun-Choi, H.S. 2002. Antiplatelet effect of the phenolic constituents isolated from the leaves of Magnolia obovata. Natural Product Sciences 8(4): 147-151.
  21. Rho, J.H., Moon, H.I., Zee, O.P. 2000. Phytochemical Constituents from Melampyrum roseum var. hirsutum Beauv. Korean Journal of Pharmacognosy 51(2): 157-162.
  22. Shibuya, M., Abe, K., Nakahahsi, Y., Kubota S. 1978. Phenolic components from leaf oil of Illicium anisatum L. Chemical and Pharmaceutical Bulletin 26(9): 2671-2673. https://doi.org/10.1248/cpb.26.2671
  23. Yamada, K., Takada, S., Nakamura, S., Hirata, Y. 1968. Structures of anisatin and neoanisatin toxic sesquiterpenes from Illicium anisatum. Tetrahedron 24(1): 199-229. https://doi.org/10.1016/0040-4020(68)89022-2
  24. Yamade, K., Takada, S., Nakamura, S., Hirata, Y. 1965. Structure of anisatin. Tetrahedron Letters 52: 4797-4801.