The Chemical Constituents of the Stem Barks of Fraxinus rhynchophylla

물푸레나무(Fraxinus rhynchophylla) 수피의 추출성분

  • Yang, Eun-Ju (School of Applied Biosciences, College of Agriculture and Life Sciences, Kyungpook National University) ;
  • Lee, Dong-Geun (Agrobiotechnology Education Center, Kyungpook National University) ;
  • Lee, Jong-Won (Catholic University of Daegu) ;
  • Kim, Yae-Sil (Hypoxy Co., Ltd., Catholic University of Daegu) ;
  • Lim, Sun-Ha (Hypoxy Co., Ltd., Catholic University of Daegu) ;
  • Song, Kyung-Sik (School of Applied Biosciences, College of Agriculture and Life Sciences, Kyungpook National University)
  • 양은주 (경북대학교 농업생명과학대학 응용생명과학부) ;
  • 이동근 (경북대학교 생물건강.농업생명 인재양성사업단) ;
  • 이종원 (대구가톨릭대학교 의과대학) ;
  • 김예실 ((주)하이폭시) ;
  • 임선하 ((주)하이폭시) ;
  • 송경식 (경북대학교 농업생명과학대학 응용생명과학부)
  • Published : 2007.12.31

Abstract

The stem barks of Fraxinus rhynchophylla was extracted with 95% EtOH, and the concentrated extract was successively partitioned with $CH_2Cl_2$, n-BuOH, and $H_2O$ in order to investigate the major phytochemicals. From the $CH_2Cl_2$ soluble fraction, a sterol (1) was isolated through the repeated silica gel column chromatographies. Three additional compounds (2-4) were isolated from the n-BuOH soluble fraction through silica gel, RP-18, and Sephadex LH-20 column chromatographies. Their chemical structures were elucidated as daucosterol $(1;{\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside)$, caffeic acid (2), 6,8-dihydroxy-7-methoxycoumarin (3), and coniferaldehyde glucoside (4) by comparing their spectral data with those in the literatures. All isolates (1-4) were the first to be isolated from F. rhynchophylla.

References

  1. Korea Forest Research Institute (1994) In Properties and uses of Korean trees. Korea Forest Research Institute, Korea
  2. Hur, J. (1994) In Dongeuibogam. Yeokangchoolpansa, Korea
  3. Ham, Y. H., Kim, J. H., Lee, S. K. and Bae, Y. S. (1997) B-4 In Proceeding of the Korea Society of Wood Science Technology (autumn). pp. 127-130, The Korea Society of Wood Science Technology, Korea
  4. Bae, Y. S. and Kim, J. K. (2000) Extractives of the bark of ash and elm as medicinal hardwood tree species. Mokchae Konghak 28, 62-69
  5. Steeves, V., Forster, H., Pommer, U. and Savidge, R. (2001) Coniferyl alcohol metabolism in conifers-I. Glucosidic turnover of cinnamyl aldehydes by UDPG: coniferyl alcohol glucosyltransferase from pine cambium. Phytochemistry 57, 1085-1093 https://doi.org/10.1016/S0031-9422(01)00107-8
  6. Slacanin, I., Marston, A., Hostettmann, K., Guedon, D. and Abbe, P. (1991) Eleutherococcus senticosus constituents by centrifugal partition chromatography and their quantitative determination by high performance liquid chromatography. Phytochemical Analysis 2, 137-142 https://doi.org/10.1002/pca.2800020310
  7. Liu, L., Wang, R., Chen, L., Wu, P. and Wang, L. (2003) Study on chemical constituents of bark of Fraxinus rhynchophylla. Zhongcaoyao 34, 889-890
  8. Kayser, O. and Kolodziej, H. (1995) Highly oxygenated coumarins from Pelargonium sidoides. Phytochemistry 39, 1181-1185 https://doi.org/10.1016/0031-9422(95)00166-5
  9. Kim, T. W. (1996) In The wood plants of Korea. Kyo Hak Sa, Korea
  10. Moghaddam, F. M., Farimani, M. M., Salahvarzi, S. and Amin, G. (2006) Chemical constituents of dichloromethane extract of cultivated Satureja khuzistanica. eCAM 2006, 1-4
  11. Kim, C. M., Shin, M. K., Ahn, D. G. and Lee, G. S. (1998) In Joongyakdaesajun. Jung Dam, Korea
  12. Kim, H. C., An, R. B., Jeong, G. S., Oh, S. H. and Kim, Y. C. (2005) 1,1-Diphenyl-2-picrylhydrazyl radical scavenging compounds of Fraxini Cortex. Natural Products Sciences 11, 150-154
  13. Kostova, I., Sidjimov, A., Kostova, V. and Dimov, S. (1994) Phytochemical investigation of Fraxinus excelsior leaves. Dokladi na Bulgarskata Akademiya na Naukite 47, 45-48
  14. Wei, X. L., Yang, C. H. and Liang, J. Y. (2005) Constituents of the barks of Fraxinus Chinensis Roxb. Zhongguo Tianran Yaowu 3, 228-230
  15. Exarchou, V., Troganis, A., Gerothanassis, I. P., Tsimidou, M. and Boskou, D. (2001) Identification and quantification of caffeic acid rosmarinic acid in complex plant extracts by the use of variable-temperature two-dimensional nuclear magnetic resonance spectroscopy. J. Agric. Food Chem. 49, 2-8
  16. Kayser, O. and Kolodziej, H. (1995) Highly oxygenated coumarins from Pelargonium sidoides. Phytochemistry 39, 1181-1185 https://doi.org/10.1016/0031-9422(95)00166-5
  17. Kim, J. K., Lee, S. K., Ham, Y. H. and Bae, Y. S. (2002) Extractives from the barks of Quercus acutissima and Quercus variabilis. J. Kor. For. En. 21, 41-48
  18. Beecher, C. W. W., Farnsworth, N. R. and Gyllenhaal, C. (1989) Pharmacologically active secondary metabolites from wood. In Natural Products of Wood Plants, pp. 1059-1163, J. W. Rowe, Germany
  19. Kim, N. Y., Pae, H., Ko, Y. S., Yoo, J. C., Choi, B. M., Jun, C. D., Chung, H. T., Inagaki, M., Higuchi, R. and Kim, Y. C. (1999) In vitro inducible nitric oxide synthesis inhibitory active constituents from Fraxinus rhynchophylla. Planta Med. 65, 656-658 https://doi.org/10.1055/s-2006-960840
  20. Issifova, T., Mikhova, B. and Kostova, I. (1993) A secoiridoid glucoside and a phenolic compound from Fraxinus ornus bark. Phytochemistry 34, 1373-1376 https://doi.org/10.1016/0031-9422(91)80032-V
  21. Kanchanapoom, T., Picheansoonthon, C., Kasai, R. and Yamasaki, K. (2001) New glucosides from Thai medicinal plant, Balanophora latisepala. Natural Medicines 55, 213-216
  22. Kim, T. J. (1995) In Herbs of Korea. Kugil media, Korea
  23. Wang, G., Wu, T., Lin, P., Chou, G. and Wang, Z. (2003) Triterpenoids isolated from Aster tataricus. Zhongcaoyao 34, 875-876
  24. Takeda, Y., Tateoka, S., Masuda, T., Otsuka, H., Honda, G., Takaishi, Y., Ito, M., Khodzhimatov, O. K. and Ozodbek, A. (2001) A new neoclerodance diterpenoid from Scutellaria hematochlora. Heterocycles 55, 1141-1145 https://doi.org/10.3987/COM-01-9190
  25. Kwon, Y. S. and Kim, C. M. (1996) A study on the chemical constituents from leaves of Fraxinus rhynchophylla. Kor. J. Pharmacogn. 27, 347-349