Antioxidant Activity of the Extractives from the Needles of Picea abies Karsten

독일가문비(Picea abies Karsten) 잎 추출성분의 항산화 활성

  • Lee, Sang-Keug (Department of Wood Chemistry & Microbiology, Korea Forest Research Institute) ;
  • Bae, Young-Soo (Department of Wood Science & Engineering, College of Forest Sciences, Kangwon National University)
  • 이상극 (국립산림과학원 화학미생물과) ;
  • 배영수 (강원대학교 산림과학대학 임산공학과)
  • Received : 2006.05.04
  • Accepted : 2006.06.16
  • Published : 2006.12.31

Abstract

The dried needles (1.5 kg) of Picea abies Karsten were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of n-hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-n-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$-, $^{13}C$-NMR, FAB and EI-MS. (+)-catechin (compound I), (-)-epicatechin (compound II), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound III), 4-hydroxyacetophenone (compound IV) were isolated from the ethyl acetate soluble fraction and (+)-catechin (compound I), protocatechuic acid (compound V) were isolated from the $H_2O$ soluble fraction of P. abies needle. The antioxidative activities of each fraction and the isolated compounds were tested by DPPH radical scavenging method, and EtOAc soluble fraction, (+)-catechin and (-)-epicatechin showed similar values to ${\alpha}$-tocopherol and BHT as controls.

독일가문비(Picea ahies Karsten) 잎을 채취하여 건조시킨 후 분쇄하여 1.5 kg을 acetone-$H_2O$(7:3, v/v)로 추출하고 핵산, 메틸렌클로라이드, 에틸아세테이트 및 물 가용부로 분획하여 동결건조 시켰다. 에틸아세테이트 및 물 가용부를 Sephadex LH-20으로 충진한 칼럼에서 MeOH와 EtOH-n-hexane 혼합액을 용출용매로 사용하여 칼럼크로마토그래피를 실시하였다. 단리된 화합물들은 셀룰로오스 박층크로마토그래피(TLC)로 확인한 후 $^1H$-, $^{13}C$-NMR 등의 스펙트럼을 사용하여 정확한 구조를 규명하였고 FAB 및 El-MS로써 분자량을 측정하였다. 독일가문비 잎의 에틸아세테이트 가용부에는 (+)-catechin(화합물 I), (-)-epicatechin(화합물 II), kaempferol-3-O-${\beta}$-D-glucopyranoside(화합물 III), 4-hydroxyacetophenone(화합물 IV)가 분리되었으며 물 가용부에서는 (+)-catechin(화합물 I)과 protocatechuic acid(화합물 V)가 분리되었다. 각 분획물 및 단리된 화합물들은 DPPH 라디칼 소거법을 이용하여 항산화 시험을 실시하였으며, 분획물중에는 에틸아세테이트 가용부, 그리고 화합물중에는 (T)-catechin과 (-)-epicatechin에서 기준물질과 유사한 우수한 항산화 효능이 있는 것으로 나타났다.

Keywords

References

  1. 김태욱. 1996. 한국의 수목. 교학사. pp. 15-49
  2. 이창복. 1985. 대한식물보감. 향문사. pp. 59-68
  3. 임업연구원. 1987. 한국수목도감. pp.496
  4. 함연호. 2000. 사시나무屬와 버드나무屬 丰要 樹種 街皮의 抽出成分에 関한 硏究. 강원대학교 박사학위논문
  5. Agrawal, P.K. 1989. Carbon-13 NMR of flavonoids. Elsevier
  6. Cha, B.C., S.B. Lee, T.J. Rhim, and K.H. Lee. 2000. Constituents of Antioxidative Activity and Free Radical Scavenging Effect from Galla Rhois (Rhus javanica Linne). Kor. J. Pharmacognosy. 31(2): 185-189
  7. Foo, L.Y., Y. Lu, A.L. Molan, D.R. Woodfield, and W.C. McNabb. 2000. The phenols and prodelphinidins of white clover flowers. Phytochemistry. 54: 539-548 https://doi.org/10.1016/S0031-9422(00)00124-2
  8. Harborne, J.B. and T.J. Mabry. 1982. The Flavonoids: advances in research. Chapman and Hall Ltd
  9. Ho, H.M., R.Y. Chen, L.K. Leung, F.L. Chan, Y. Huang, and Z.Y. Chen. 2002. Difference in flavonoid and isoflavone profile between soybean and soyleaf. Biomed Pharmacother. 56: 289-295 https://doi.org/10.1016/S0753-3322(02)00191-9
  10. Kim, J.K., W.G. Park, and Y.S. Bae. 1997. Flavonoid glycosides from needles of Larix leptolepis (Pinaceae). Mokchaekonghak. 25(2): 81-87
  11. Kim, J.K., Y.S. Bae. 2001. Extractives from the needles of Torreya. Mokchaekonghak. 29(4): 53-59
  12. Lee, S.K., W.G. Park, and Y.S. Bae. 1997. Procyanidins from Lindera obtusiloba Bark. Mokchaekonghak. 25(2): 110-116
  13. Moreno, A., M. Cordero, I. Guerra, and M.V. Toro. 2002. Flavonoids form Dorycnium rectum. Biochemical Systematics and Ecology. 30: 73-74 https://doi.org/10.1016/S0305-1978(01)00070-9
  14. Ohara, S.R. and W. Hemingway. 1989. The phenolic extractives in southern red oak (Quercus falcata Michx. vex.falcatav bark. Holzforschung. 43: 149-154 https://doi.org/10.1515/hfsg.1989.43.3.149
  15. Rasmussen, S., C. Wolff, and H. Rudolph. 1995. Compartmentalization of Phenolic Constituents in Sphagnum. Phytochemistry. 38(1): 35-39 https://doi.org/10.1016/0031-9422(94)00650-I
  16. Shao, Y, Y.L. Li, and B.N. Zhou. 1996. Phenolic and Triterpenoid Glycosides from Aster Batangensis. Phytochemistry. 41 (6): 1593-1598 https://doi.org/10.1016/0031-9422(95)00219-7
  17. Ternai, B. and K.R. Markham. 1976. $Carbon-^{13}NMR$ studies of flavonoids-I: f1avones and flavonols. Tetrahedron. 32: 565-569 https://doi.org/10.1016/S0040-4020(01)93772-X