Chinese Journal of Organic Chemistry >
Diterpenoids from the Needles of the Endangered Plant Pinus dabeshanensis and Their Protein Tyrosine Phosphatase 1B Inhibitory Effects
Received date: 2017-01-04
Revised date: 2017-02-19
Online published: 2017-03-08
Supported by
Project 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).
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.
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
[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.
[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.
[3] Editorial Committee Flora of China, Science Press, Beijing, 1978, Vol. 7, pp. 32~211(in Chinese). (中国科学院中国植物志编辑委员会, 中国植物志, 第7卷, 科学出版社, 北京, 1978, pp. 32~211.)
[4] Fu, L.-K.; Jin, J.-M. China Plant Red Data Book. Rare and Endangered Plants I, Science Press, Beijing, 1992(in Chinese). (傅立国, 金鉴明, 中国植物红皮书-稀有濒危植物(第一册), 科学出版社, 北京, 1992.)
[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] Hu, C.-L.; Xiong, J.; Gao, L.-X.; Li, J.; Zeng, H.-Q.; Zou, Y.; Hu, J.-F. RSC Adv. 2016, 6, 1832.
[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.
[8] Wenkert, E.; Buckwalter, L. J. Am. Chem. Soc. 1972, 94, 4367.
[9] Wang, H.; Lin, B.; Liu, X.; Zhang, J.; Xia, M. Green Chem. 2008, 10, 1190.
[10] Palkin, S.; Harris, T. H. J. Am. Chem. Soc. 1934, 56, 1935.
[11] Zhao, Y.-X.; Zhou, L.; Guo, L.; Luo, X.-D.; Zhou, J. J. Asian Nat. Prod. Res. 2005, 7, 259.
[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.
[13] Mills, J. S. J. Chem. Soc. C 1967, 2514.
[14] Bohlmann, F.; Czerson, H. Phyrochemistry 1979, 18, 115.
[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.
[16] Dauben, W. G.; German, V. F. Tetrahedron 1966, 22, 679.
[17] Fang, J.-M.; Lang, C.-I.; Chen W.-L.; Cheng Y.-S. Phytochemistry 1991, 30, 2793.
[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] Li, Y.; Wang, T.-T.; Zhao, J.; Shi, X.; Hu, S.-C.; Gao, K. Food Chem. 2012, 131, 972.
[20] Liang, L.-F.; Kurtan, T.; Mandi, A.; Yao, L.-G.; Li, J.; Zhang, W.; Guo, Y.-W. Org. Lett. 2013, 15, 274.
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