식용식물자원으로부터 활성물질의 탐색-XV. 머위(Petasites japonicus)잎으로부터 Triterpene 배당체의 분리

Development of Biologically Active Compound from Edible Plant Sources-XV. Isolation of Triterpene Glycosides from the Leaf of Petasites japonicus

  • 방면호 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 박진규 ((주)파마코디자인) ;
  • 송명종 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 양혜정 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 유종수 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 안은미 ((주)싸이제닉) ;
  • 김대근 (우석대학교 약학대학) ;
  • 백남인 (경희대학교 생명공학원 및 식물대사연구센터)
  • Bang, Myun-Ho (The Graduate School of Biotechnology & Plant Metabolism Research Center) ;
  • Park, Jin-Kyu (Pharmaco Design Co. Ltd.) ;
  • Song, Myoung-Chong (The Graduate School of Biotechnology & Plant Metabolism Research Center) ;
  • Yang, Hye-Joung (The Graduate School of Biotechnology & Plant Metabolism Research Center) ;
  • Yoo, Jong-Su (The Graduate School of Biotechnology & Plant Metabolism Research Center) ;
  • Ahn, Eun-Mi (Scigenic Co. Ltd.) ;
  • Kim, Dae-Keun (Department of Pharmacy, Woosuk University) ;
  • Baek, Nam-In (The Graduate School of Biotechnology & Plant Metabolism Research Center)
  • 발행 : 2005.12.31

초록

머위 잎을 80% MeOH수용액으로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH 및 $H_2O$로 용매 분획하였다. EtOAc 분획에 대하여 silica gel과 ODS column chromatography를 반복하여 2종의 triterpenoid 화합물을 분리하였다. 각 화합물은 $^1H-{^1H}$ gCOSY, gHMBC 및 gHSQC와 같은 2D-NMR기법을 포함한 스펙트럼 데이터를 해석하여 rosamutin(1) 및 peduncloside(2)로 구조를 결정하였다.

The leaf of Petasites japonicus was extracted with 80% aqueous MeOH and solvent fractionated with EtOAc, n-BuOH and water successively. From the EtOAc fractions, two triterpenoids were isolated through the repeated silica gel and ODS column chromatographies. The chemical structures of the isolated terpenoids were determined as rosamutin (1) and peduncloside (2) through the interpretation of several spectral data including 2D-NMR such as $^1H-{^1H}$ gCOSY, gHSQC and gHMBC.

키워드

참고문헌

  1. Soka, T. (1985) In Dictionary of Chinese Drugs (1st ed.) Shanghai Science Technology Shogakukan Press, Tokyo
  2. Kikuchi, M. (1973) Studies on the constituents of the flower stalk of Petasites japonicus Maxim VII. on the components of the volatile oil. Yakugaku Zasshi. 93, 123-126
  3. Jung, E. B. and Shin, M. K. (1990) In HyangYakDaeSaJun (3rd ed.), Young Lim Sa Press, Seoul
  4. Yaoita, Y. and Kikuchi, M. (1994) Eremopetasidione a Norsesquiterpenoid from the rhizomes of Petasites japonicus. PhytoChem. 37, 1765-1766 https://doi.org/10.1016/S0031-9422(00)89608-9
  5. Yaoita, Y. and Kikuchi, M. (1994) Petasiphenone a phenolic compound from rhizomes of Petasites japonicus. PhytoChem. 37, 1773-1774 https://doi.org/10.1016/S0031-9422(00)89612-0
  6. Yaoita, Y. and Kikuchi, M. (1994) Structures of six new eremophilenolides from the rhizomes of Petasites japonicus. Chem. Pharm. Bull. 42, 1944-1947
  7. Choi, O. B. (2002) Anti-allergic effects of Petasites japonicus. Korean J. Food Nutr. 15, 382-385
  8. Jee, Y. H. and Lee, C. S. (1996) Pathological changes on rats and mice fed with Petasites japonicus. Maxim. Korean J. Vet. Res. 36, 417-428
  9. Zhong, J. J., Xiang, Q. L. and Zi, M. L. (1993) Triterpenoids from Sanguisorba alpina. Phytochem. 32, 155-159 https://doi.org/10.1016/0031-9422(92)80123-V
  10. Nakatani, M., Miyazaki, Y., Iwashita, T., Naoki, H. and Hase, T. (1989) Triterpenoids from Ilex rotunda fruits. Phytochem. 28, 1479-1482 https://doi.org/10.1016/S0031-9422(00)97768-9
  11. Simoes, C. M. O., Amoros, M. and Girre, L. (1999) Mechanism of antiviral activity of triterpenoid saponins. Phytother. Res. 13, 323-328 https://doi.org/10.1002/(SICI)1099-1573(199906)13:4<323::AID-PTR448>3.0.CO;2-C
  12. Jung, H. J., Nam, J. H., Choi, J., Lee, K. T. and Park, H. J. (2005) 19$\alpha$-Hydroxyursane-Type triterpenoids: antinociceptive anti-inflammatory principles of the roots of Rosa rugosa. Biol. Pharm. Bull. 28, 101-104 https://doi.org/10.1248/bpb.28.101
  13. Jahromi, M. A., Gupta, M., Manickam, M., Ray, A. B. and Chansouria, J. P. (1999) Hypolipidemic activity of pedunculoside a constituent of Ilex doniana; Pharm. Biol. 37, 37-41 https://doi.org/10.1076/phbi.37.1.37.6314
  14. Ohigashi, H., Takamura, H., Koshimizu, K., Tokuda, H. and Ito, Y. (1986) Search for possible antitumor promoters by inhibition of 12-O-tetradecanoylphorbol-13-acetate-induce Epstein-Barr virus activation; ursolic acid and oleanolic acid from an antiinflamatory chinese medical plant, Glechoma hederaceae L. Cancer Lett. 30, 143-151 https://doi.org/10.1016/0304-3835(86)90082-0
  15. Jeong, T. S., Hwang, E. I., Lee, H. B., Lee, E. S., Kim, Y. K., Min, B. S., Bae, K. H., Bok, S. H. and Kim, S. U. (1979) Chitin synthase II inhibitory activity of ursolic acid, isolated from Crataegus pinnatifida. Planta Med. 65, 261-263 https://doi.org/10.1055/s-2006-960474
  16. Liu, J. (1995) Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 49, 57-68 https://doi.org/10.1016/0378-8741(95)90032-2
  17. Mahato, S. B., Nandy, A. K. and Roy, G. (1992) Triterpenoids. Phytochem. 31, 2199-2249 https://doi.org/10.1016/0031-9422(92)83257-Y
  18. Yang, H. S., Chung, H., Lee, C. K., Park, K. Y., Yokozawa, T. and Oura, H. (1994) Ursolic acid inhibits aflatoxin Bl-induced mutagenicity in a Salmonella assay system. Biol. Pharm. Bull. 17, 990-992