Journal of the Korean Wood Science and Technology

The Korean Society of Wood Science & Technology (한국목재공학회)
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Stilbenoids of Korean Pine (Pinus koraiensis) Inner Bark

  • 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)
  • Received : 2009.07.24
  • Accepted : 2009.09.01
  • Published : 2009.09.25
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Abstract

Pinus koraiensis inner bark was collected and extracted with 95% ethanol. The extracts were concentrated and then sequentially fractionated using n-hexane, $CH_2Cl_2$, EtOAc, and $H_2O$ to be freeze dried. A portion of EtOAc fraction (6.6 g) was chromatographed on a Sephadex LH-20 column using aqueous methanol to isolate (+)-catechin (1), (-)-epicatechin (2), and trans-pinostilbenoside (3). Resveratrol (4) and trans-pinostilbene (5) were isolated by column chromatography using EtOH-hexane mixture after purification with aqueous methanol. The structures of these stilbenosides and flavans were characterized by spectroscopic tools using NMR and MS.

Keywords

Acknowledgement

Supported by : Korea Forest Service

References

  1. Commodari, F., A. Khiat, S. Ibrahimi, A. R. Brizius, and N. Kalkstein. 2005. Comparison of the phytoestrogen trans-resveratrol (3,4',5-trihydroxystilbene) structures from x-ray diffraction and solution NMR. Magnetic Resonance in Chemistry 43(7): 567-572 https://doi.org/10.1002/mrc.1583
  2. Gromova, A. S., N. A. Tyukavkina, V. I. Lutskii, G. A. Kalabin, and D. F. Kushnarev. 1975. Hydroxystilbenes of the inner bark of Pinus sibirica. Chemistry of Natural Compounds 11(6): 715-719 https://doi.org/10.1007/BF00568450
  3. Harbone, J. B. and T. J. Mabry. 1982. The flavonoids: advance in research, Chapman and Hall Ltd. pp. 421-426
  4. Kim, B. R. and A. Mishiro. 1998, Studies on Variability of Wood Properties in Stem of Pinus koraiensis (II)-Differences in Tracheid Length, Microfibril Angle and Compressive Strength on the South and North Sides of Stem-. Journal of Korean Wood Science and Technology 26(2): 45-51
  5. Kim, J. J., H. K. Song, and C. H. Han. 2001. Antifungal activities of extracts from the various parts of the genus Pinus trees. Journal of the Korean Society for Applied Biological Chemistry 44(4): 269-272
  6. Koh, D., K. H. Park, J. Jung, H. Yang, K. Hun Mok, and Y. Lim. 2001. Complete assignment of the 1H and 13C NMR spectra of resveratrol derivatives. Magnetic Resonance in Chemistry 39 (12): 768-770 https://doi.org/10.1002/mrc.910
  7. Lee, H. J., Y. J. Choi, D. H. Choi, and I. P. Hong. 2003. Extractives of Pinus koraiensis wood. Journal of Korean Wood Science and Technology 31(5): 49-56
  8. Mirov, N. T. 1967. The Genus Pinus. Ronald, New York
  9. Miura, T., S. Muraoka, N. Ikeda, M. Watanabe, and Y. Fujimoto. 2000. Antioxidative and prooxidative action of stilbene derivatives. Pharmacology & Toxicology 86(5): 203-208 https://doi.org/10.1034/j.1600-0773.2000.d01-36.x
  10. Regev-Shoshani, G., O. Shoseyov, I. Bilkis, and Z. Kerem. 2003. Glycosylation of resveratrol protects it from enzymic oxidation. Biochemical Journal 374(1): 157-163 https://doi.org/10.1042/BJ20030141
  11. Rimando, A. M. and N. Suh. 2008. Biological/ chemopreventive activity of stilbenes and their effect on colon cancer. Planta Medica 74(13): 1635-1643 https://doi.org/10.1055/s-0028-1088301
  12. Singh, I. P., H. Etoh, E. Asai, K. Kikuchi, K. Ina, K. Koyasu, and Y. Terada. 1997. Flavonoids and stilbenes as repellents against the blue mussel, Mytilus edulis galloprovincialis. Natural Product Sciences 3(1): 49-54
  13. Shimizu, K., R. Kondo, and K. Sakai. 2000. Inhibition of tyrosinase by flavonoids, stilbenes, and related 4-substituted resorcinols. Structureactivity investigations. Planta Medica 66(1): 11 https://doi.org/10.1055/s-2000-11113
  14. Song, H. K. 2001. Isolation and Identification of Stilnene glycosides from the Bark of Pinus koraiensis. Journal of Korean Wood Science and Technology 34(6): 51-60
  15. Song, H. K., J. H. Jung, K. H. Park, and Y. H. Lim. 2001. Leukotriene D4 antagonistic activity of a stilbene derivative isolated from the bark of Pinus koraiensis. Agricultural Chemistry & Biotechnology 44(4): 199-201
  16. Vidakovic, M. 1991. Conifers: Morphology and Variation. Crafickizavod Hrvatske, Croatia