Citation: Li Ming, Hu Changlin, Han Han, Xiong Juan, Hu Jinfeng. Diterpenoids from the Needles of the Endangered Plant Pinus dabeshanensis and Their Protein Tyrosine Phosphatase 1B Inhibitory Effects[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1860-1863. doi: 10.6023/cjoc201701002 shu

Diterpenoids from the Needles of the Endangered Plant Pinus dabeshanensis and Their Protein Tyrosine Phosphatase 1B Inhibitory Effects

Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai 201203

Corresponding author: Hu Jinfeng, jfhu@fudan.edu.cn
Received Date: 4 January 2017
Revised Date: 19 February 2017
Available Online: 8 July 2017
Fund Project: the National Natural Science Foundation of China 81273401the National Natural Science Foundation of China 21472021the National Basic Research Program of China (973 Program) 2013CB530700the Ph.D. Programs Foundation of Ministry of Education of China 20120071110049the Ph.D. Programs Foundation of Ministry of Education of China 20120071120049Project supported by the National Natural Science Foundation of China (Nos. 21472021, 81273401, 81202420), the Ph.D. Programs Foundation of Ministry of Education of China (Nos. 20120071110049, 20120071120049), and the National Basic Research Program of China (973 Program, No. 2013CB530700)the National Natural Science Foundation of China 81202420

Figures(3)

One new, dabeshanensin L (1), and nine known diterpenoids with diverse structures were isolated from the 90% MeOH extract of the needles (30 g dried mass-limited samples) of Pinus dabeshanensis, an endangered conifer listed in the China Plant Red Data Book (CPRDB). The new structure was established by detailed analysis of its spectroscopic data (IR, 1D/2D NMR, HRMS). Among the isolates, isopimara-7-en-18-oic acid (4), trans-abienol (6), and lambertianic acid (8) showed significant inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B) enzyme, a key target for the treatment of type-Ⅱ diabetes and obesity, with IC₅₀ values ranging from 14.6 to 37.7 μmol/L.
- endangered plant,
- Pinus dabeshanensis,
- diterpenoids,
- dabeshanensin L,
- PTP1B inhibition
1. [1]
  Ibrahim, M. A.; Na, M.; Oh, J.; Schinazi, R. F.; McBrayer, T. R.; Whitaker, T.; Doerksen, R. J.; Newman, D. J.; Zachos, L. G.; Hamann, M. T. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 16832. doi: 10.1073/pnas.1311528110
2. [2]
  Zhu, F.; Qin, C.; Tao, L.; Liu, X.; Shi, Z.; Ma, X.; Jia, J.; Tan, Y.; Cui, C.; Lin, J.; Tan, C.; Jiang, Y.; Chen, Y. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 12943. doi: 10.1073/pnas.1107336108
3. [3]
  Editorial Committee Flora of China, Science Press, Beijing, 1978, Vol. 7, pp. 32~211(in Chinese).
4. [4]
  Fu, L.-K.; Jin, J.-M. China Plant Red Data Book. Rare and Endangered Plants I, Science Press, Beijing, 1992(in Chinese).
5. [5]
  The State Forestry Administration and the Ministry of Agriculture List of Wild Plants of National Priority Protection I, 1999. http://www.gov.cn/gongbao/content/2000/content_60072.htm.
6. [6]
  Hu, C.-L.; Xiong, J.; Gao, L.-X.; Li, J.; Zeng, H.-Q.; Zou, Y.; Hu, J.-F. RSC Adv. 2016, 6, 1832.
7. [7]
  Yang, X.-W.; Feng, L.; Li, S. M.; Liu, X.-H.; Li, Y.-L.; Wu, L.; Shen, Y.-H.; Tian, J.-M.; Zhang, X.; Liu, X.-R.; Wang, N.; Liu, Y.-H.; Zhang, W.-D. Bioorg. Med. Chem. 2010, 18, 744. doi: 10.1016/j.bmc.2009.11.055
8. [8]
  Wenkert, E.; Buckwalter, L. J. Am. Chem. Soc. 1972, 94, 4367. doi: 10.1021/ja00767a070
9. [9]
  Wang, H.; Lin, B.; Liu, X.; Zhang, J.; Xia, M. Green Chem. 2008, 10, 1190. doi: 10.1039/b803295e
10. [10]
  Palkin, S.; Harris, T. H. J. Am. Chem. Soc. 1934, 56, 1935. doi: 10.1021/ja01324a032
11. [11]
  Zhao, Y.-X.; Zhou, L.; Guo, L.; Luo, X.-D.; Zhou, J. J. Asian Nat. Prod. Res. 2005, 7, 259. doi: 10.1080/10286020410001690163
12. [12]
  Yang, X.-W.; Li, S.-M.; Feng, L.; Shen, Y.-H.; Tian, J.-M.; Liu, X.-H.; Zeng, H.-W.; Zhang, C.; Zhang, W.-D. Tetrahedron 2008, 64, 4354. doi: 10.1016/j.tet.2008.02.069
13. [13]
  Mills, J. S. J. Chem. Soc. C 1967, 2514.
14. [14]
  Bohlmann, F.; Czerson, H. Phyrochemistry 1979, 18, 115. doi: 10.1016/S0031-9422(00)90926-9
15. [15]
  Asili, J.; Lambert, M.; Ziegler, H. L.; Stærk, D.; Sairafianpour, M.; Witt, M.; Asghari, G.; Ibrahimi, I. S.; Jaroszewski, J. W. J. Nat. Prod. 2004, 67, 631. doi: 10.1021/np034033e
16. [16]
  Dauben, W. G.; German, V. F. Tetrahedron 1966, 22, 679. doi: 10.1016/0040-4020(66)80037-6
17. [17]
  Fang, J.-M.; Lang, C.-I.; Chen W.-L.; Cheng Y.-S. Phytochemistry 1991, 30, 2793. doi: 10.1016/0031-9422(91)85148-S
18. [18]
  Hu, C.-L.; Xiong, J.; Li, J.-Y.; Gao, L.-X.; Wang, W.-X.; Cheng, K.-J.; Yang, G.-X.; Li, J.; Hu, J.-F. Eur. J. Org. Chem. 2016, 1832.
19. [19]
  Li, Y.; Wang, T.-T.; Zhao, J.; Shi, X.; Hu, S.-C.; Gao, K. Food Chem. 2012, 131, 972. doi: 10.1016/j.foodchem.2011.09.089
20. [20]
  Liang, L.-F.; Kurtan, T.; Mandi, A.; Yao, L.-G.; Li, J.; Zhang, W.; Guo, Y.-W. Org. Lett. 2013, 15, 274. doi: 10.1021/ol303110d
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