大别山五针松松针中二萜成分及其蛋白酪氨酸磷酸酶1B抑制活性研究
收稿日期: 2017-01-04
修回日期: 2017-02-19
网络出版日期: 2017-03-08
基金资助
国家自然科学基金（Nos.21472021，81273401，81202420）、教育部高等学校博士学科点（博导类）基金（Nos.20120071110049，20120071120049）和国家重点基础研究发展规划（973计划，No.2013CB530700）资助项目.
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).
从濒危植物大别山五针松（Pinus dabeshanensis）松针（干重仅30 g）的90%甲醇提取物中分离得到10个二萜类化合物，其中新化合物dabeshanensin L（1）的结构是通过运用1D/2D NMR等波谱手段进行确证的.体外活性测试结果表明化合物isopimara-7-en-18-oic acid（4）、trans-abienol（6）和lambertianic acid（8）对蛋白酪氨酸磷酸酶1B（PTP1B）有显著的抑制作用，其IC50值在14.6~37.7 μmol/L之间.
关键词： 濒危植物; 大别山五针松; 二萜; dabeshanensin L; PTP1B抑制活性
李明 , 胡长玲 , 韩晗 , 熊娟 , 胡金锋 . 大别山五针松松针中二萜成分及其蛋白酪氨酸磷酸酶1B抑制活性研究[J]. 有机化学, 2017 , 37(7) : 1860 -1863 . DOI: 10.6023/cjoc201701002
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.
[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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