Isolation of Phenolic Glucosides from the Stems of Acer tegmentosum Max

산겨릅나무 줄기에서 페놀성 글루코사이드의 분리

  • Hur, Jong-Moon (School of Applied Biosciences, College of Agriculture and Life Sciences, Kyungpook National University) ;
  • Yang, Eun-Ju (Agrobiotechnology Education Center, Kyungpook National University) ;
  • Choi, Sun-Ha (School of Applied Biosciences, College of Agriculture and Life Sciences, Kyungpook National University) ;
  • Song, Kyung-Sik (School of Applied Biosciences, College of Agriculture and Life Sciences, Kyungpook National University)
  • 허종문 (경북대학교 농업생명과학대학 응용생명과학부) ;
  • 양은주 (생물건강.농업생명 인재양성사업단) ;
  • 최선하 (경북대학교 농업생명과학대학 응용생명과학부) ;
  • 송경식 (경북대학교 농업생명과학대학 응용생명과학부)
  • Published : 2006.06.01

Abstract

The chemical constituents of Acer tegmentosum Max which belongs to Aceraceae has never been reported. The stems of A. tegmentosum were extracted with MeOH and then successively partitioned with $CH_2Cl_2$, n-BuOH, and $H_2O$ in order to investigate the major phytochemicals. Two compounds were isolated from the n-BuOH fraction through silica gel and RP-18 column chromatographies. Their chemical structures were elucidated as methyl gallate $4-O-{\beta}-D-glucoside$ and salidroside by comparing their spectral data with those in the literature.

산겨릅나무(A. tegmentosum)의 성분 연구를 위하여 줄기를 MeOH로 추출하여 $CH_2Cl_2$, n-BuOH 및 $H_2O$ 순으로 분획하였다. n-BuOH fraction에 대하여 silica gel과 RP-18 column chromatography를 행하여 2종의 화합물을 분리하였다. 이들 화합물의 구조는 spectral data를 문헌치와 비교하여 methyl gallate $4-O-{\beta}-D-glucoside(1)$와 salidroside(2)로 동정하였다. 이들 화합물은 산겨릅나무에서 처음으로 분리되었다.

Keywords

References

  1. Lee T. B. (1993) In Illustrated flora of Korea. Hyang Mun Sa, Seoul, Korea
  2. Shu, P. G. (1994) In Atlas of Chinese Materia Medica, Yeogang Publisher, Seoul, Korea
  3. Yang, H., Sung, S. H. and Kim Y. C. (2005) Two new heptatoprotective stilbene glycosides form Acer mono leaves. J. Nat. Prod. 68, 101-103 https://doi.org/10.1021/np0497907
  4. Yang, H., Lee, M. K. and Kim, Y. C. (2005) Protective activities of stilbene glycosides from Acer mono leaves against $H_{2}O_{2}$-induced oxidative damage in primary cultured rat hepatocytes. J. Agric. Food Chem. 53, 4182-4186 https://doi.org/10.1021/jf050093+
  5. Park, W. Y. (1996) Phenolic compounds from Acer ginnala Maxim. Kor. J. Pharmacogn. 27, 212-218
  6. Son, Y. K. and Han, Y. N. (2002) Isolation of triterpenoid saponins from the stems of Acer ginnala Maxim. Kor. J. Pharmacogn. 33, 301-304
  7. Oh, H. S., Cui, C. B., Choi, H. T., Kim, S. H., Jeon, M. S. and Ham, S. S. (2004) Antimutagenic and cytototoxic effects of Acer ginnala Marx. bark extracts. Kor. J. Food Preserv. 11, 550-556
  8. Han, S. S., Lo, S. C., Choi, Y. H., Kim, M. J. and Kwak, S. S. (1999) Antioxidative compoounds in extracts of Acer ginnala Max. Kor. J. Med. Crop Sci. 7, 51-57
  9. Kim, H. Y. and Oh, J. H. (1999) Screening of Korean forest plants for rat lens aldose reductase inhibition. Biosci. Biotechnol. Biochem. 63, 184-188 https://doi.org/10.1271/bbb.63.184
  10. Park, J. G., Park, J. C., Hur, J. M., Park, S. J., Choi, D. R., Shin, D. Y., Park, K. Y., Cho, H. W. and Kim, M. S. (2000) Phenolic compounds from Orostachys japonicus having anti-HIV protease activity. Nat. Prod. Sci. 6, 117-121
  11. Schuster. B., Winter, M. and Herrmann, K. (1986) 4-O-$\beta$-DGlucosides of hydroxybenzoic acid and hydroxycinnamic acids - their synthesis and determination in berry fruit and vegetable. J. Biosci. 41, 511-520
  12. Kim, S. J., Kim, K. S., Hwang, S. J., Chon, S. U., Kim ,Y. H., Ahn, J. C. and Hwang, B. (2004) Identification of salidroside from Rhodiola sachalinensis A. Bor. and its production through cell suspension culture. Kor. J. Med. Crop Sci. 12, 203-208
  13. Adam, K. P. (1999) Phenolic constituents of the fern Phegopteris connectilis. Phytocemistry 52, 929-934 https://doi.org/10.1016/S0031-9422(99)00326-X
  14. Lee, J. S., Kim, H. J., Park, H. and Lee, Y. S. (2002) New diarylheptanoids from the stems of Carpinus cordata. J. Nat. Prod. 65, 1367-1370 https://doi.org/10.1021/np020048l
  15. Kashiwada, Y., Nonaka, G. H. and Noshioka, I. (1986) Tannins and related compounds. XLVII. Rhubarb. (6). Isolation and characterization of new p-hydroxyphenylbutanones, stilbenes and gallic acid glucosides. Chem. Pharm. Bull. 34, 3237-3243 https://doi.org/10.1248/cpb.34.3237
  16. Han, X., Zhang, T., Wei, Y., Cao, X. and Ito, Y. (2002) Separation of salidroside from Rhodiola crenulata by highspeed counter-current chromatography. J. Chromatogr. A 971, 237-241 https://doi.org/10.1016/S0021-9673(02)01041-5
  17. Hase, T., Kawamoto, Y., Ohtani, K., Kasai, R., Yamasaki, K. and Picheansoonthon, C. (1995) Cyclohexylethanoids and related glucosides from Millingtonia hortensis. Phytochemistry 39, 235-241 https://doi.org/10.1016/0031-9422(94)00939-Q
  18. Jang, S. I., Pae, H. O., Choi, B. M., Oh, G. S., Jeong, S., Lee, H. J., Kim, H. Y., Kang, K. H., Yum, Y. G., Kim, Y. C. and Chung, H. T. (2003). Salidroside form Rhodiola sachalinensis protects neuronal PC12 cells against cytotoxicity induced by amyloid-$\beta$. Immunopharmacol. Immunotoxicol. 25, 295-304 https://doi.org/10.1081/IPH-120024498
  19. Zhang, Y. and Liu, Y.(2005) Study on effects of salidroside on lipid peroxidation on oxidative stress in rat hepatic stellate cells. Zhong Yao Cai 28, 794-796
  20. Zhang, X. S., Zhu, B. D., Hung, X. Q. and Chen, Y. F. (2005) Effect of salidroside on bone marrow cell cycle and expression of apoptosis-related proteins in bone marrow cells of bone marrow depressed anemia mice. Sichuan Da Xue Xue Bao Yi Xue Ban 36, 820-823
  21. Wang, S. H., Wang, W. J., Wang, X. F., Chen, W. H. (2004) Effects of salidroside on carbohydrate metabolism and differentiation of 3T3-L1 adipocytes. Zhong Xi Yi Jie He Xue Bao 2, 193-195 https://doi.org/10.3736/jcim20040312