Coumarins and Chromones from Angelica genuflexa

  • An, Ren-Bo (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology,College of Pharmacy, Yanbian, University) ;
  • Park, Bo-Young (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Jung-Hee (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kwon, Ok-Kyoung (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Joong-Ku (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Min, Byung-Sun (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Ahn, Kyung-Seop (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Oh, Sei-Ryang (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Hyeong-Kyu (Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology)
  • Published : 2005.06.01

Abstract

Thirteen compounds were isolated from the roots of Angelica genuflexa through repeated silica gel column chromatography. Nine coumarins, isoimperatorin (1), osthol (2), demethylsuberosin (3), oxypeucedanin (4), heraclenin (5), pabulenol (7), umbelliferone (8), oxypeucedanin hydrate (9) and marmesinin (11), and four chromones, hamaudol (6), cimifugin (10), sec-O-glucosylhamaudol (12) and prim-O-glucosylcimifugin (13), were identified by physicochemical and spectroscopic analysis. Among these, compounds 3, 5, 6, 8, 12, and 13 were isolated for the first time from the roots of Angelica genuflexa. These coumarins and chromones were examined for their anticomplement activity. Demethylsuberosin (3) showed a weak anticomplement activity with an $IC_{50}$ value of $390\;{\mu}M$.

Keywords

References

  1. Bae, K., Ji, J.M., Kang, J.S., and Ahn, B.Z., A cytotoxic component from Angelica koreana Radix against L1210 and HL-60 cells. Arch. Pharm. Res., 17,45-47 (1994) https://doi.org/10.1007/BF02978248
  2. Baek, N.I., Ahn, E.M., Kim, H.Y., and Park, Y.D., Furanocoumarins from the root of Angelica dahurica. Arch. Pharm. Res., 23, 467-470 (2000) https://doi.org/10.1007/BF02976574
  3. Fujioka, T., Furumi, K., Fujii, H., Okabe, H., Mihashi, K, Nakano, Y., Matsunaga, H., Katano, M., and Mori, M., Antiproliferative constituents from Umbelliferae plants. V. A new furancoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chem. Pharm. Bull., 47, 96-100 (1999) https://doi.org/10.1248/cpb.47.96
  4. Jung, K.Y., Oh, S.R., Park, S.H., Lee, I.S., Ahn, K.S., Lee, J.J., and Lee, H.K., Anti-complement activity of tiliroside from the flower buds of Magnolia fargesii. Biol. Pharm. Bull., 21, 1077 -1078 (1998) https://doi.org/10.1248/bpb.21.1077
  5. Kwon, Y.S., In, K.K., and Kim, C.M., Chemical constituents from the roots of Ostericum koreanum. Kor. J Pharmacogn. 13, 284-287 (2000)
  6. Kwon, Y.S., Woo, E.R., and Kim, C.M., A study on the constituents of bioactive fractions of Ostericum koreanum Kitagawa. Kor. J Pharmacogn. 22, 156-161 (1991)
  7. Lee, C.K. and Woo, W.S., Coumarin Constituents from the Roots of Angelica koreana Max. Kor. J. Pharmacog., 13, 10-13 (1982)
  8. Lee, Y.Y., Lee, S., Jin, J.J., and Yun-Choi, H.S., Platelet antiaggregatory effects of coumarins from the roots of Angelica genuflexa and A. gigas. Arch. Pharm. Res., 26, 723-726 (2003) https://doi.org/10.1007/BF02976681
  9. Masuda, T., Takasugi, M., and Anetai, M., Psoralen and other linear furanocoumarins as photoalexins in Glehnia littoralis. Phytochemistry, 47, 13-16 (1998) https://doi.org/10.1016/S0031-9422(97)00528-1
  10. Matano, Y., Okuyama, T., Shibata, S., Hoson, M., Kawada, T., Osada, H., and Noguchi, T., Studies on coumarins of a Chinese drug 'qian-hu'; VII. Structures of new coumarin-glycosides of zihua qian-hu and effect of coumarin-glycosides on human platelet aggregation. Planta Med., 52, 135-138 (1986) https://doi.org/10.1055/s-2007-969099
  11. Min, B.S., Lee, S.Y., Kim, J.H., Lee, J.K., Kim, T.J., Kim, D.H., Kim, Y.H., Joung, H., Lee, H.K, Nakamura, N., Miyashiro, H., and Hattori, M., Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. Biol. Pharm. Bull., 26, 1042-1044 (2003) https://doi.org/10.1248/bpb.26.1042
  12. Okuyama, E., Hasegawa, T., Matsushita, T., Fujimoto, H., Ishibashi, M., and Yamazaki, M., Analgesic components of saposhnikovia root (Saposhnikovia divaricata). Chem. Pharm. Bull., 49, 154-160 (2001) https://doi.org/10.1248/cpb.49.154
  13. Razdan, T.K., Qadri, B., Harkar, S., and Waight, E. S., Chromones and coumarins from Skimmia laureola. Phytochemistry, 26, 2063-2069 (1987) https://doi.org/10.1016/S0031-9422(00)81759-8
  14. Ryu, K.S., The chemical structure of koreanin isolated from the roots Angelica koreana Maximowicz. Yakhak Hoeji 12, 65-71 (1968)
  15. Ryu, S.Y., Kou, N.Y., Choi, H.S., Ryu, H., Kim, T.S., and Kim, K. M., Cnidicin, a coumarin, from the root of Angelica koreana, inhibits the degranulation of mast cell and the NO generation in RAW 264.7 cells. Planta Med. 67, 172-174 (2001) https://doi.org/10.1055/s-2001-11509
  16. Sasaki, H., Taguchi, H., Endo, T., and Yosioka, I., The constituents Ledebouriella seseloides Wolff. I. Structures of three new chromones. Chem. Pharm. Bull., 30, 3555-3562 (1982) https://doi.org/10.1248/cpb.30.3555
  17. Sun, B.Y., Kim, T.J., Kim, S.T., Suh, Y.B., and Kim, C.H., Systematics of Ostericum (Apiaceae) in Korea. Kor. J. Plant Tax., 30, 93-104 (2000)
  18. Woo, W.S., Lee, C.K., and Shin, K.H., Isolation of drug metabolism modifiers from roots of Angelica koreana. Planta Med., 45, 234-236 (1982) https://doi.org/10.1055/s-2007-971379
  19. Zhou, P., Takaishi, Y., Drum, H., Chen, B., Honda, G, Itoh, M., Takeda, Y., Kodzhimatov, O.K, and Lee, K.-H., Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry, 53, 689-697 (2000) https://doi.org/10.1016/S0031-9422(99)00554-3