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

doi:10.6023/cjoc201701002

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1860-1863.DOI: 10.6023/cjoc201701002 Previous Articles Next Articles

Notes

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

李明, 胡长玲, 韩晗, 熊娟, 胡金锋

复旦大学药学院天然药物化学教研室上海 201203

收稿日期:2017-01-04 修回日期:2017-02-19 发布日期:2017-03-08
通讯作者: 胡金锋 E-mail:jfhu@fudan.edu.cn
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

Li Ming, Hu Changlin, Han Han, Xiong Juan, Hu Jinfeng

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

Received:2017-01-04 Revised:2017-02-19 Published:2017-03-08
Contact: 10.6023/cjoc201701002 E-mail:jfhu@fudan.edu.cn
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).

1. Diterpenoids from the Needles of the Endangered Plant Pinus dabeshanensis and Their Protein Tyrosine Phosphatase 1B Inhibitory Effects.PDF(611KB)

Abstract

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.

Key words: endangered plant, Pinus dabeshanensis, diterpenoids, dabeshanensin L, PTP1B inhibition

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(7): 1860-1863.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

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

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Wang Lijun, Lau Choiwan, Xiong Juan, Hu Jinfeng. Further Chemical Constituents from the Rare Chloranthaceae Plant Chloranthus sessilifolius [J]. Chin. J. Org. Chem., 2016, 36(7): 1677-1680.
[2]	Du Mingjun, Lei Xiaoguang. Advanced in the Synthesis of Kaurane Diterpenoids [J]. Chin. J. Org. Chem., 2015, 35(12): 2447-2464.