Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Flavonol Glycosides from the Aerial Parts of Metaplexis japonica

박주가리 지상부로부터 Flavonol Glycoside 성분의 분리

  • Lee, So-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
  • 이소영 (서울대학교 약학대학 천연물과학연구소) ;
  • 김주선 (서울대학교 약학대학 천연물과학연구소) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소)
  • Received : 2012.08.10
  • Accepted : 2012.09.10
  • Published : 2012.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Ten flavonol glycosides were isolated from the EtOAc fraction of the MeOH extract of Metaplexis japonica Makino. Structures of the flavonoids were elucidated on the basis of spectroscopic data and comparison with literature values. The flavonoids were found to be mostly common flavonol 3-glycosides. It is of interest that the sacchaide parts of the isolates were pairs of arabinosides, glucosides, galactosides, rutinosides and robinobiosides of kaempferol and quercetin. All of these compounds were isolated for the first time from this plant.

Keywords

References

  1. Bae, K.-H. (2000) Medicinal Plants of Korea, 414, Kyo-Hak Publishing Co., Ltd., Seoul.
  2. Mitsuhashi, H., Nomura, T., Shimizu, Y., Takemori, I. and Yamada, E. (1962) Studies on the constituents of Asclepiadaceae plants. VIII. On the components of Metaplexis japonica Makino. 1. Chem. Pharm. Bull. 10: 811-817. https://doi.org/10.1248/cpb.10.811
  3. Mitsuhashi, H. and Nomura, T. (1964) On the structure of ramanone. Steroids 3: 271-276. https://doi.org/10.1016/0039-128X(64)90036-4
  4. Mitsuhashi, H. and Nomura, T. (1964) On the structure of pergularin. Chem. Pharm. Bull. 12: 1523-1525. https://doi.org/10.1248/cpb.12.1523
  5. Nomura, T. and Mitsuhashi, H. (1972) Components of Metaplexis japonica Makino. Chem. Pharm. Bull. 20: 1344-1347. https://doi.org/10.1248/cpb.20.1344
  6. Mitsuhashi, H. and Nomura, T. (1965) Studies on the constituents of Asclepiadaceae plants. XV. On the components of Metaplexis japonica Makino. II. Chem. Pharm. Bull. 13: 274-280. https://doi.org/10.1248/cpb.13.274
  7. Mitsuhashi, H. and Nomura, T. (1965) Studies on the constituents of Asclepiadaceae plants. XVI. On the components of Metaplexis japonica Makino. III. The structure of benzoylramanone. Chem. Pharm. Bull. 13: 1332-1340. https://doi.org/10.1248/cpb.13.1332
  8. Mitsuhashi, H., Nomura, T. and Hirano, M. (1966) Studies on the constituents of Asclepiadaceae plants. XIX. Components of Metaplexis japonica Makino. IV. Chem. Pharm. Bull. 14: 717-726. https://doi.org/10.1248/cpb.14.717
  9. Nomura, T., Yamada, S. and Mitsuhashi, H. (1979) Studies on the constituents of Asclepiadaceae plants. XIV. On the components of Metaplexis japonica Makino. VI. The structures of 7-oxygenated-pregnane derivatives. Chem. Pharm. Bull. 27: 508-514. https://doi.org/10.1248/cpb.27.508
  10. Nomura, T., Fukai, T. and Kuramochi, T. (1981) Components of Metaplexis japonica Makino. VII. Structure of a new 7- oxygenated pregnane derivative. Planta Med. 41: 206-207. https://doi.org/10.1055/s-2007-971705
  11. Warashina, T. and Noro, T. (1998) Steroidal glycosides from the roots of Metaplexis japonica. Phytochemistry 49: 2103- 2108. https://doi.org/10.1016/S0031-9422(98)00405-1
  12. Warashina, T. and Noro, T. (1998) Steroidal glycosides from the roots of Metaplexis japonica M. Part II. Chem. Pharm. Bull. 46: 1752-1757. https://doi.org/10.1248/cpb.46.1752
  13. Kim, H. C., Bu, Y. M., Kim, M. Y., Kim, J. G., Park, J. Y., Song, M. K., Nirmala, J. and Nabaraj, P. (2010) Composition containing Metaplexis japonica extract or fraction for preventing and treating neurodegenerative diseases. Repub. Korean Kongkae Taeho Kongbo, Pat. no. 1020100052119.
  14. Begum, A. S., Sahai, M., Fujimoto, Y., Asai, K., Schneider, K., Nicholson, G. and Suessmuth, R. (2006) A new kaempferol diglycoside from Datura suaveolens Humb. & Bonpl. ex. Willd. Nat. Prod. Res. 20: 1231-1236. https://doi.org/10.1080/14786410600905816
  15. Park, S. Y., Kim, J. S., Lee, S. Y., Bae, K. H. and Kang, S. S. (2008) Chemical constituents of Lathyrus davidii. Nat. Prod. Sci. 14: 281-288.
  16. Fraisse, D., Heitz, A., Carnat, A., Carnat, A.-P. and Lamaison, J.-L. (2000) Quercetin 3-arabinopyranoside, a major flavonoid compound from Alchemilla xanthochlora. Fitoterapia 71: 463-464. https://doi.org/10.1016/S0367-326X(00)00145-3
  17. Arima, H. and Danno, G.-I. (2002) Isolation of antimicrobial compounds from Guava (Psidium guajava L.) and their structural elucidation. Biosci. Biotechnol. Biochem. 66: 1727-1730. https://doi.org/10.1271/bbb.66.1727
  18. Yean, M. H., Kim, J. S., Hyun, J. W., Bae, K.-H. and Kang, S. S. (2012) Tritepenoids and Phenolics from Geum japonicum. Kor. J. Pharmacogn. 43: 107-121.
  19. Kim, J. S., Kang, S. S., Lee, M. W. and Kim, O. K. (1995) Isolation of flavonoids from the leaves of Aralia continentalis. Kor. J. Pharmacogn. 26: 239-243.
  20. Kazuma, K., Noda, N. and Suzuki, M. (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62: 229-237. https://doi.org/10.1016/S0031-9422(02)00486-7
  21. Nahrstedt, A., Hungeling, M. and Petereit, F. (2006) Flavonoids from Acalypha indica. Fitoterapia 77: 484-486. https://doi.org/10.1016/j.fitote.2006.04.007
  22. Brasseur, T. and Angenot, L. (1986) Flavonol glycosides from leaves of Strychnos variabilis. Phytochemistry 25: 563-564. https://doi.org/10.1016/S0031-9422(00)85534-X
  23. Kang, S. S., Cordell, G. A., Soejarto, D. D. and Fong, H. H. S. (1985) Alkaloids and flavonoids from Ricinus communis. J. Nat. Prod. 48: 155-156. https://doi.org/10.1021/np50037a041
  24. Sankara Subramanian, S. and Nair, A. G. R. (1968) Flavonoids of some Asclepiadaceous Plants. Phytochemistry 7: 1703-1704. https://doi.org/10.1016/S0031-9422(00)88630-6
  25. Heneidak, S., Grayer, R. J., Kite, G. C. and Simmonds, M. S. J. (2006) Flavonoid glycosides from Egyptian species of the tribe Asclepiadeae (Apocynaceae, subfamily Asclepiadoideae). Biochem. System. Ecol. 34: 575-584 https://doi.org/10.1016/j.bse.2006.03.001
  26. Perkin, A. G. (1909) CCXXXIV.-The colouring matter of cotton flowers. Gossypium herbaceum. Part II. J. Chem. Soc., Trans. 95: 2181-2193.
  27. Attree, G. F. and Perkin, A. G. (1927) XXXVI.-The position of the sugar nucleus in the quercetin glucosides. J. Chem. Soc. 234-240.
  28. Ice, C. H. and Wender, S. H. (1952) The synthesis of isoquercitrin. J. Am. Chem. Soc. 74: 4606. https://doi.org/10.1021/ja01138a048
  29. The Merck Index (2001). Thirteenth ed., 934. Merck & Co., Inc., Whitehouse Station, NJ.
  30. Harborne, B. and Baxter, H. (1999) The Handbook of Natural Flavonoids. Vol. 1, John Wiley & Sons, Chichester.
  31. Steinegge, E., Sonanin, D. and Tsingarida, K. (1963) Solanceae flavones. III. Flavonoids of belladonna leaf. Pharm. Acta Helv. 38: 119-124
  32. Farkas, L., Vermes, B., Ngrdi, M. and Klmn, A. (1976) The final structure of robinin and biorobin and their total synthesis. Phytochemistry 15: 215-218. https://doi.org/10.1016/S0031-9422(00)89088-3