Phenolic Compounds from Acer tegmentosum Bark

산겨릅나무 수피의 페놀성 화합물

  • Kwon, Dong-Joo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Bae, Young-Soo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University)
  • 권동주 (강원대학교 산림환경과학대학 임산공학과) ;
  • 배영수 (강원대학교 산림환경과학대학 임산공학과)
  • Received : 2007.08.28
  • Accepted : 2007.09.17
  • Published : 2007.11.25

Abstract

To investigate the chemical constituents of Acer tegmentosum, the bark were collected, air-dried and extracted with 70% aqueous acetone. Then it was successively partitioned with n-hexane, $CH_2Cl_2$, EtOAc and $H_2O$. Repeated Sephadex LH-20 column chromatography on the EtOAc soluble fraction gave five phenolic compounds. Their structures were elucidated as (+)-catechin (1), (-)-epi-catechin (2), Q-epicatechin-3-O-gallate (3), gallic acid (4) and 6'-0-galloylsalidroside (5) on the basis of spectroscopic evidences using $^1H-NMR$, $^{13}C-NMR$, 2D-NMR and MS spectroscopy, (-)-epicatechin-3-Ogallate (3), gallic acid (4), 6'-Ogalloylsalidroside (5) have not been reported in this plant yet.

산겨릅나무 수피의 성분 연구를 위해 수피를 채취하여 70% 아세톤 용액으로 추출하고 농축한 후 분획깔때기로 헥산, 디클로로메탄, 에틸아세테이트 및 수용성으로 순차 추출하여 동결건조하였다. 에틸아세테이트용성 분획에 대하여 Sephadex LH-20 칼럼크로마토그래피를 반복적으로 수행하여 5개의 페놀성 화합물을 분리하였다. 화합물의 구조는 $^1H-NMR$, $^{13}C-NMR$, 2D-NMR 및 MS 스펙트럼을 분석하여, (+)-catechin (1), (-)-epicatechin (2), (-)-epicatechin-3-O-gallate (3), gallic acid (4) 및 6''-O-galloylsalidroside (5)으로 동정하였다. (-)-epicatechin-3-O-gallate (3), gallic acid (4), 6''-O-galloylsalidroside (5)는 산겨릅나무 수피에서 처음 분리되었다.

Keywords

References

  1. 김태욱. 1996. 한국의 수목, 교학사. p.476
  2. 조재명 외 12명. 2003. 원색 약용-식용 수목도설. 유성사. p. 163
  3. Agrawal, P. K. 1989. Carbon-13 NMR of flavonoids. Elsevier. pp. 437-445
  4. An, B. J., W. K. Kim, J.Y. Choi, I. B. Kwon, and C. Choi. 1992. Structure and isolation of xanthine oxidase inhibitor from Oolong Tea, Korean J. Food Sci. Technol 24(6): 558-562
  5. Chang, C. W., F. L. Hsu, and J. Y. Lin. 1994. Inhibitory effects of polyphenolic catechins from chinese green tea on HIY reverse transcriptase activity. J. Biomed. Sci. 1: 163-166 https://doi.org/10.1007/BF02253344
  6. Davis, A. L. Y. Cai, A. P. Davies, and J. R. Lewis. 1996. $^1H$ and $^{13}C$ NMR assignments of some green tea polyphenols. Magn. Reson. Chem. 34(11): 887-890 https://doi.org/10.1002/(SICI)1097-458X(199611)34:11<887::AID-OMR995>3.0.CO;2-U
  7. Harbone, J. B. and T. J. Mabry. 1982. The flavonoids: advance in research. Chapman and Hall Ltd. pp. 421-426
  8. Hur, J. M., M. Jun, E.J. Yang, S. H. Choi, J. C. Park, and K. S. Song. 2007. Isolation of isoprenoidal compounds from the stem of Acer tegmentosum Max. Kor.J. Pharmacogn. 38(1): 67-70
  9. Hur, J. M., E. J. Yang, S. H. Choi, and K. S. Song. 2006. Isolation of phenolic glucosides from the stems of Acer tegmentosum Max. J. Korean Soc Appl. Biol. Chem 49(2): 149-152
  10. Jung, H. Y. and T. Yokozawa. 1995. Studies on Antioxidative and antimutagenic mechanisms of epicatechin 3-O-gallate isolated from green tea. Korean J. Food Sci. Technol. 28(4): 46-58
  11. Kim, J. K. and Y. S. Bae. 2006. Chemical constituents of domestic Quercus spp. leaves.J. Korean Wood Sci. Technol. 34(6): 61-71
  12. Nonaka, G. I., H. Nishimura, and I. Nishioka. 1982. Tannins and related compounds. IV. Seven new phenol glucoside gallates from Quercus stenophylla Makino. Chem. Pharm. Bull. 30(6): 2061-2067
  13. Park, K. M., M.C., Yang. K. H. Lee, S. U. Choi, and K. R. Lee. 2006. Cytotoxic phenolic constituents of Acer tegmentosum Maxim. Arch Pharm Res. 29(12): 1086-1090 https://doi.org/10.1007/BF02969296
  14. Shin, I. C., J. H. Sa, T. H. Shim, and J. H. Lee. 2006. The physical and chemical properties and cytotoxic effects of Acer tegmentosum Maxim. Extracts. J. Korean Soc. Appl. Biol. Chem. 49(4): 322-327.