Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Sesquiterpenoids from the heartwood of Juniperu s chinensis

  • Jung, Hee Jin (Department of Food and Life Science, Pukyong National University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu) ;
  • Jung, Hyun Ah (Department of Food Science and Human Nutrition, Chonbuk National University) ;
  • Choi, Jae Sue (Department of Food and Life Science, Pukyong National University)
  • Received : 2017.04.05
  • Accepted : 2017.06.10
  • Published : 2017.09.29
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Abstract

A new sesquiterpenoid, 11-hydroxy-valenc-1(10),3(4)-dien-2-one (3), two chemically synthesized but first isolate from nature, $3-oxocedran-8{\beta}-ol$ (1) and valenc-1(10),3(4),11(12)-trien-2-one (2) along with four known compounds, sugiol (4), (+)-nootkatone (5), 11-hydroxy-valenc-1(10)-en-2-one (6), and clovandiol (7), were isolated from the heartwood of Juniperus chinensis. All chemical structures were elucidated using extensive spectroscopic analysis including 1D and 2D NMR spectroscopy. Valenc-1(10),3(4),11(12)-trien-2-one (2) exhibited significant inhibitory activity against butyrylcholinesterase with an $IC_{50}$ value of $68.45{\mu}M$.

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References

  1. Corner, E. J. H. Wayside Trees of Malaya; Malayan Nature Society: Malaysia, 1988, pp 396-446.
  2. But, P. P. H.; Kimura, T.; Gue, J. X.; Sung, C. K. International Collation of Traditional and Folk Medicine; World Scientific Publishing Co., Ltd.: Singapore, 1997, pp 16-17.
  3. Jung, H. J.; Jung, H. A.; Min, B. S.; Choi, J. S. Chem. Pharm. Bull. 2015, 63, 955-960. https://doi.org/10.1248/cpb.c15-00504
  4. Ellman, G. L.; Courtney, K. D.; Andres, V. Jr.; Feather-stone, R. M. Biochem. Pharmacol. 1961, 7, 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
  5. Hanson, J. R.; Nasir, H. Phytochemistry 1993, 33, 835-837. https://doi.org/10.1016/0031-9422(93)85285-Y
  6. Gand, E.; Hanson, J. R.; Nasir, H. Phytochemistry 1995, 39, 1081-1084. https://doi.org/10.1016/0031-9422(95)00120-V
  7. Collins, D. O.; Reese, P. B. Phytochemistry 2001, 56, 417-421. https://doi.org/10.1016/S0031-9422(00)00412-X
  8. Caine, D.; Chu, C. Y. Tetrahedron Lett. 1974, 15, 703-706. https://doi.org/10.1016/S0040-4039(01)82309-1
  9. Caine, D.; Chu, C. Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797. https://doi.org/10.1021/jo01307a013
  10. Pesaro, M.; Bozzato, G.; Schudel, P. Chem. Commun (London). 1968, 19, 1152-1154.
  11. Kuo, Y. H.; Wu, T. R.; Cheng, M. C.; Wang, Y. Chem. Pharm. Bull. 1990, 38, 3195-3201. https://doi.org/10.1248/cpb.38.3195
  12. Chang, C. I.; Chen, W. C.; Shao, Y. Y.; Yeh, C. R.; Yang, N. S.; Chiang, W.; Kuo, Y. H. Nat. Prod. Res. 2008, 22, 1158-1162. https://doi.org/10.1080/14786410601132444
  13. Savona, G.; Piozzi, F.; De La Torre, M. C.; Servettaz, O. Rodríguez, B. Phytochemistry 1987, 26, 571-572. https://doi.org/10.1016/S0031-9422(00)81458-2
  14. Xu, J.; Su, J.; Li, Y.; Tan, N. Chem. Nat. Compd. 2013, 49, 457-461. https://doi.org/10.1007/s10600-013-0638-5
  15. Zhang, C.; Zhou, A.; Zhang, M. China Journal of Chinese Materia Medica 2009, 34, 994-998.
  16. Furusawa, M.; Hashimoto, T.; Noma, Y.; Asakawa, Y. Chem. Pharm. Bull. 2005, 53, 1513-1514. https://doi.org/10.1248/cpb.53.1513
  17. Naf, F.; Decorzant, R.; Thommen, W. Helv. Chim. Acta 1982, 65, 2212-2223. https://doi.org/10.1002/hlca.19820650726
  18. Wittayalai, S.; Mahidol, C.; Prachyawarakorn, V.; Prawat, H.; Ruchirawat, S. Phytochemistry 2014, 99, 121-126. https://doi.org/10.1016/j.phytochem.2013.12.017

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