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.

물푸레나무(F. rhynchophylla)의 수피를 95% EtOH로 추출하여 얻어진 추출물을 $CH_2Cl_2$, n-BuOH 및 $H_2O$ 순으로 분획하였다. 이 중 $CH_2Cl_2$, 가용성 분획에 대하여 silica gel column chromatography를 실시하여 1종의 sterol 화합물(1)을 분리하였다. 한편 n-BuOH 가용성 분획에 대해서도 silica gel, RP-18 및 Sephadex LH-20 등의 충진제를 사용하여 column chromatography를 행하여 3종의 phenylpropanoid 화합물(2-4)을 얻었다. 각 화합물의 구조는 $^1H-NMR$와 LC-MS data를 해석하고 문헌과 비교하여 daucosterol(1), caffeic acid(2), 6,8-dihydroxy-7-methoxycoumarin(3) 및 coniferaldehyde glucoside(4)로 동정하였다. 이들 화합물은 진피에서 처음으로 분리되었다.

Keywords

References

  1. Kim, T. W. (1996) In The wood plants of Korea. Kyo Hak Sa, Korea
  2. Kim, T. J. (1995) In Herbs of Korea. Kugil media, Korea
  3. Korea Forest Research Institute (1994) In Properties and uses of Korean trees. Korea Forest Research Institute, Korea
  4. Kim, C. M., Shin, M. K., Ahn, D. G. and Lee, G. S. (1998) In Joongyakdaesajun. Jung Dam, Korea
  5. Hur, J. (1994) In Dongeuibogam. Yeokangchoolpansa, Korea
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. Wang, G., Wu, T., Lin, P., Chou, G. and Wang, Z. (2003) Triterpenoids isolated from Aster tataricus. Zhongcaoyao 34, 875-876
  17. 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
  18. 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
  19. 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
  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. 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
  22. 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
  23. 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
  24. 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
  25. Kanchanapoom, T., Picheansoonthon, C., Kasai, R. and Yamasaki, K. (2001) New glucosides from Thai medicinal plant, Balanophora latisepala. Natural Medicines 55, 213-216