Original article |
|
|
|
|
|
Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata |
Lai-Bin Zhang1,2, Chun Lei1, Li-Xin Gao3, Jing-Ya Li3, Jia Li3, Ai-Jun Hou1 |
1. Department of Pharmacognosy, School of Pharmacy, Fudan University, 826 Zhang Heng Road, Shanghai 201203, People's Republic of China; 2. Department of Chinese Medicine, School of Pharmacy, Xinxiang Medical University, 601 Jin Sui Road, Xinxiang 453003, People's Republic of China; 3. National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 189 Guo Shou Jing Road, Shanghai 201203, People's Republic of China |
|
|
Abstract Three new C-methylated and isoprenylated chalcone derivatives, dentichalcones A-C (1-3), together with six known compounds (4-9), were isolated from the twigs and leaves of Macaranga denticulata. Their structures were elucidated by spectroscopic analysis, including 1D, 2D NMR, and MS data. The known compounds, (2E)-1-(5,7-dihydroxy-2,2,6-trimethyl-2H-benzopyran-8-yl)-3-(4-methoxyphenyl)-2-propen-1-one (4), (2E)-1-(5,7-dihydroxy-2,2-dimethyl-2H-benzopyran-8-yl)-3-phenyl-2-propen-1-one (5), laxichalcone (6), macarangin (7), bonanniol A (8), and bonannione A (9), showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) in vitro. Graphical Abstract Three new C-methylated and isoprenylated chalcone derivatives, dentichalcones A-C (1-3), together with six known compounds, were isolated from the twigs and leaves of Macaranga denticulata. Some compounds showed inhibitory activities against PTP1B in vitro.
|
Keywords
Macaranga denticulata
Euphorbiaceae
Isoprenylated flavonoids
Dentichalcones A-C
Protein tyrosine phosphatase 1B
|
Fund:Financial support from the National Natural Science Foundation of China (Nos.81222045,21372049);the Specialized Research Fund for the Doctoral Program of Higher Education of China (20130071120104);and the Shu Guang Project (No.12SG02) from Shanghai Municipal Education Commission and Shanghai Education Development Foundation is gratefully acknowledged |
Issue Date: 08 February 2018
|
|
|
1. B. Botta, A. Vitali, P. Menendez, D. Misiti, G.D. Monache, Curr. Med. Chem. 12, 713-739 (2005) 2. G. Webster, Ann. Missouri Bot. Garden 81, 33-144 (1994) 3. A. Nick, T. Rali, O. Sticher, J. Ethnopharmacol. 49, 147-156 (1995) 4. S.J. Wei, J. Guangxi. Tradit. Chin. Med. 15, 36-39 (1992) 5. D.S. Yang, Z.L. Li, X. Wang, H. Yan, Y.P. Yang, H.R. Luo, K.C. Liu, W.L. Xiao, X.L. Li, RSC Adv. 5, 13886-13890 (2015) 6. D.S. Yang, Z.L. Li, W.B. Peng, Y.P. Yang, X. Wang, K.C. Liu, X.L. Li, W.L. Xiao, Fitoterapia 103, 165-170 (2015) 7. S. Sutthivaiyakit, S. Unganont, P. Sutthivaiyakit, A. Suksamrarn, Tetrahedron 58, 3619-3622 (2002) 8. B.J. Goldstein, A. Bittner-Kowalczyk, M.F. White, M. Harbeck, J. Biol. Chem. 275, 4283-4289 (2000) 9. M. Wang, L.X. Gao, J. Wang, J.Y. Li, M.H. Yu, J. Li, A.J. Hou, Phytochemistry 109, 140-146 (2015) 10. M. Wang, B.W. Yu, M.H. Yu, L.X. Gao, J.Y. Li, H.Y. Wang, J. Li, A.J. Hou, Chem. Biodivers. 12, 937-945 (2015) 11. C.C. Liu, C. Lei, Y. Zhong, L.X. Gao, J.Y. Li, M.H. Yu, J. Li, A.J. Hou, Tetrahedron 70, 4317-4322 (2014) 12. H.B. Liao, C. Lei, L.X. Gao, J.Y. Li, J. Li, A.J. Hou, Org. Lett. 17, 5040-5043 (2015) 13. L. Xia, Y.R. Lee, Bull. Korean Chem. Soc. 32, 2921-2927 (2011) 14. A.G. Kanthasamy, G.A. Kraus, V. Anantharam, U. S. Pat. Appl. Publ. US 20110112182 A1 20110512 (2011) 15. Y.L. Lin, Y.L. Chen, Y.H. Kuo, Chem. Pharm. Bull. 40, 2295-2299 (1992) 16. M. Bruno, G. Savona, L. Lamartina, F. Lentini, Heterocycles 23, 1147-1153 (1985) 17. Y.N. Zhang, W. Zhang, D. Hong, L. Shi, Q. Shen, J.Y. Li, J. Li, L.H. Hu, Bioorg. Med. Chem. 16, 8697-8705 (2008) 18. R.R. Kulkarnia, S.G. Tupeb, S.P. Gamplec, M.G. Chandgudea, D. Sarkarc, M.V. Deshpandeb, S.P. Joshia, Nat. Prod. Res. 28, 245-250 (2014) 19. A. Daikonya, S. Katsuki, S. Kitanaka, Chem. Pharm. Bull. 52, 1326-1329 (2004) 20. T. Tanaka, T. Ito, M. Iinuma, Y. Takahashi, H. Naganawa, Phytochemistry 48, 1423-1427 (1998) 21. M. Furusawa, Y. Ido, T. Tanaka, T. Ito, K. Nakaya, I. Ibrahim, M. Ohyama, M. Iinuma, Y. Shirataka, Y. Takahashi, Helv. Chim. Acta 88, 1048-1058 (2005) 22. K.K.M. Kulju, S.E.C. Sierra, S.G.A. Draisma, R. Samuel, P.C. van Welzen, Am. J. Bot. 94, 1726-1743 (2007) 23. L. Shi, H.P. Yu, Y.Y. Zhou, J.Q. Du, Q. Shen, J.Y. Li, J. Li, Acta Pharmacol. Sin. 29, 278-284 (2008) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|