Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
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Phytochemical Studies on Lonicera Caulis (1) - Sterols and Triterpenoids

인동의 성분연구 (1) - Sterol 및 Triterpenoid 화합물

  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Yean, Min-Hye (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Lee, So-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Lee, Je-Hyun (Department of Korean Medicine, Dongguk University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
  • 김주선 (서울대학교 약학대학 천연물과학연구소) ;
  • 연민혜 (서울대학교 약학대학 천연물과학연구소) ;
  • 이소영 (서울대학교 약학대학 천연물과학연구소) ;
  • 이제현 (동국대학교 한의과대학) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소)
  • Published : 2009.12.31
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Abstract

Twelve compounds were isolated from the 70% ethanol extract of Lonicera Caulis (Caprifoliaceae) and their structures were identified as six triterpenoids [(24S)-cycloart-25-en-$3{\beta}$,24-diol (1), pomolic acid (7), ursolic acid (8), euscaphic acid (9), hederagenin (10), and 23-hydroxytormentic acid (12)] and six sterols [obtusifoliol (2), gramisterol (3), citrostadienol (4), ${\beta}$-sitosterol (5), ergosterol peroxide (6) and ${\beta}$-sitosterol glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. All the compounds were isolated from this plant parts for the first time.

Keywords

References

  1. Son, K. H., Park, J. O., Chung, K. C., Chang, H. W., Kim, H. P., Kim, J. S. and Kang S. S. (1992) Flavonoids from the Aerial Parts of Lonicera japonica. Arch. Pharm. Res. 15, 365-370 https://doi.org/10.1007/BF02974114
  2. Son, K. H., Kim, J. S., Kang, S. S., Kim, H. P. and Chang, H. W. (1994) Isolation of flavonoids from Lonicera japonica. Kor. J. Pharmacogn. 25, 24-27
  3. Kumar, N., Singh, B., Bhandari, P., Gupta, A. P., Uniyal, S. K. and Kaul, V. K. (2005) Biflavonoids from Lonicera japonica. Phytochemistry 66, 2740-2744 https://doi.org/10.1016/j.phytochem.2005.10.002
  4. Qian, Z.-M., Li, H.-J., Li, P., Chen, J. and Tang, D. (2007) Simultaneous quantification of seven bioactive components in Caulis Lonicerae Japonicae by high performance liquid chromatography. Biomed. Chromatogr. 21, 649-654 https://doi.org/10.1002/bmc.803
  5. Lee, S. J., Shin, E. J., Son, K. H., Chang, H. W., Kang, S. S. and Kim, H. P. (1995) Antiinflammatory activity of the major constituents of Lonicera japonica. Arch. Pharm. Res. 18, 133-135 https://doi.org/10.1007/BF02979147
  6. Kawai, H., Kuroyanagi, M. and Ueno, A. (1988) Iridoid glucosides from Lonicera japonica Thunb. Chem. Pharm. Bull. 36, 3664-3666 https://doi.org/10.1248/cpb.36.3664
  7. Tomassini, L. M., Cometa, F., Serafini, M. and Nicoletti, M. (1995) Isolation of secoiridoid artifacts from Lonicera japonica. J. Nat. Prod. 58, 1756-1758 https://doi.org/10.1021/np50125a020
  8. Machida, K., Sakaki, H., Iijima, T. and Kikuchi, M. (2002) Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica Thunb. Chem. Pharm. Bull. 50, 1041-1044 https://doi.org/10.1248/cpb.50.1041
  9. Son, K. H., Jung, K. Y., Chang, H. W., Kim, H. P. and Kang, S. S. (1994) Triterpenoid saponins from the aerial parts of Lonicera japonica. Phytochemistry 35, 1005-1008 https://doi.org/10.1016/S0031-9422(00)90656-3
  10. Kwak, W. J., Han, C. K., Chang, H. W., Kim, H. P., Kang, S. S. and Son, K. H. (2003) Loniceroside C, an antiinflammatory saponin from Lonicera japonica. Chem. Pharm. Bull. 51, 333-335 https://doi.org/10.1248/cpb.51.333
  11. Yahara, S., Kobayashi, N. and Nohara, T. (1990) Studies on the triterpenoid glycosides in Lonicerae Caulis et Folium. Shoyakugaku Zasshi 44, 339-342
  12. Kawai, H., Kuroyanagi, M., Umehara, K., Ueno, A. and Satake, M. (1988) Studies on the saponins of Lonicera japonica Thunb. Chem. Pharm. Bull. 36, 4769-4775 https://doi.org/10.1248/cpb.36.4769
  13. 문태철, 박정옥, 정광원, 손건호, 김현표, 강삼식, 장현욱, 정규찬 (1999) Anti-inflammatory activity of the flavonoid components of Lonicera japonica. 약학회지 43, 117-123
  14. Lee, S. J., Son, K. H., Chang, H. W., Kang, S. S., Park, P.-U., Kwak, W.-J., Han, C.-K. and Kim, H. P. (1994) Development of plant antiinflammatory agents: Comparison of antiinflammatory and analgesic activities of extracts from Lonicera japonica. Kor. J. Pharmacogn. 25, 363-367
  15. Lee, S. J., Son, K. H., Chang, H. W., Kang, S. S. and Kim, H. P. (1998) Antiinflammatory activity of Lonicera japonica. Phytother. Res. 12, 445-447 https://doi.org/10.1002/(SICI)1099-1573(199809)12:6<445::AID-PTR317>3.0.CO;2-5
  16. Lee, S. J., Choi, J. H., Son, K. H., Chang, H. W., Kang, S. S. and Kim, H. P. (1995) Suppression of mouse lymphocyte proliferation in vitro by naturally occurring biflavonoids. Life Sci. 57, 551-558 https://doi.org/10.1016/0024-3205(95)00305-P
  17. 정대영, 이호영, 하혜경, 정다영, 강삼식, 김정숙 (2003) Induction of growth hormone release by the extracts of Lonicera japonica THUNB. 생약학회지 34, 256-262
  18. Kim, S. Y., Son, K. H., Chang, H. W., Kang, S. S. and Kim, H. P. (1999) Inhibition of mouse ear edema by steroidal and triterpenoid saponins. Arch. Pharm. Res. 22, 313-316 https://doi.org/10.1007/BF02976370
  19. Suh, S.-J., Chung, T.-W., Son, M.-J., Kim, S.-H., Moon, T.-C., Son, K.-H., Kim, H. P., Chang, H. W. and Kim, C.-H. (2006) The naturally occurring biflavonoid, ochnaflavone, inhibits LPS-induced iNOS expression, which is mediated by ERK1/2 via NF-$\kappa$B regulation, in RAW264.7 cells. Arch. Biochem. Biophys. 447, 136-146 https://doi.org/10.1016/j.abb.2006.01.016
  20. Son, M.-J., Moon, T.-C., Lee, E.-K., Son, K.-H., Kim, H. P., Kang, S. S., Son, J. K., Lee, S. H. and Chang, H. W. (2006) Naturally occurring biflavonoid, ochnaflavone, inhibits cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Arch. Pharm. Res. 29, 282-286 https://doi.org/10.1007/BF02968571
  21. Kang, Y.-J., Min, H.-Y., Hong, J.-Y., Kim, Y. S., Kang, S. S. and Lee, S. K. (2009) Ochnaflavone, a natural biflavonoid, induces cell cycle arrest and apoptosis in HCT-15 human colon cancer cells. Biomolecules & Therapeutics 17, 282-287 https://doi.org/10.4062/biomolther.2009.17.3.282
  22. Luo, H.-F., Li, Q-L., Yu, S.-G., Badger, T. M. and Fang, N.-B. (2005) Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran. J. Nat. Prod. 68, 94-97 https://doi.org/10.1021/np049889d
  23. Kitajima, J., Kimizuka, K. and Tanaka, Y. (1998) New sterols and triterpenoids of Ficus pumila fruit. Chem. Pharm. Bull. 46, 1408-1411 https://doi.org/10.1002/chin.199911208
  24. Pei, Y.-G., Wu, Q.-X. and Shi, Y.-P. (2007) Triterpenoids and other constituents from Euphorbia humifusa. J. Chin. Chem. Soc. 54, 1565-1572
  25. Greca, M. D., Fiorentino, A., Monaco, P. and Previtera, L. (1994) Cycloartane triterpenes from Juncus effusus. Phytochemistry 35, 1017-1022 https://doi.org/10.1016/S0031-9422(00)90659-9
  26. Iida, T. and Matsumoto, T. (1980) NMR spectra of sterols. J. Japan Oil Chem. Soc. 29, 141-161 https://doi.org/10.5650/jos1956.29.141
  27. Goad, L. J. and Akihisa, T. (1997) Analysis of Sterols. 396-398, Blackie Academic & Professional, London
  28. Lee, S. H., Shim, S. H., Kim, J. S. and Kang, S. S. (2006) Constituents from the fruiting bodies of Ganoderma applanatum and their aldose reductase inhibitory activity. Arch. Pharm. Res. 29, 479-483 https://doi.org/10.1007/BF02969420
  29. 강삼식, 손건호 (2000) 천연물성분 구조결정법, 서울대학교 출판부, 서울
  30. Xu, Y. N., Kim, J. S., Kang, S. S., Son, K. H., Kim, H. P., Chang, H. W. and Bae, K.-H. (2002) Components from the roots of Chaenomeles japonica. Kor. J. Pharmacogn. 33, 267-271
  31. Liang, G.-Y., Gray, A. I. and Waterman, P. G. (1989) Pentacyclic triterpenes from the fruits of Rosa sterilis. J. Nat. Prod. 52, 162-166 https://doi.org/10.1021/np50061a021
  32. Kim, Y. H. and Kang, S. S. (1993) Triterpenoids from Rubi Fructus (Bogbunja). Arch. Pharm. Res. 16, 109-113 https://doi.org/10.1007/BF03036856
  33. Dewick, P. M. (2009) Medicinal natural products. 3rd ed. 253, John Wiley & Sons, Ltd., Chichester