Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

doi:10.1007/s13659-015-0082-2

Natural Products and Bioprospecting ›› 2016, Vol. 6 ›› Issue (1): 25-30.DOI: 10.1007/s13659-015-0082-2

• Original article • Previous Articles Next Articles

Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

Lai-Bin Zhang^1,2, 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

Received:2015-12-01 Revised:2015-12-15 Online:2018-02-08 Published:2016-02-24
Supported by:
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

Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

Lai-Bin Zhang^1,2, 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

通讯作者: Ai-Jun Hou,e-mail:ajhou@shmu.edu.cn
基金资助:
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

Abstract

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.

Key words: Macaranga denticulata, Euphorbiaceae, Isoprenylated flavonoids, Dentichalcones A-C, Protein tyrosine phosphatase 1B

摘要： 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.

关键词: Macaranga denticulata, Euphorbiaceae, Isoprenylated flavonoids, Dentichalcones A-C, Protein tyrosine phosphatase 1B

Lai-Bin Zhang, Chun Lei, Li-Xin Gao, Jing-Ya Li, Jia Li, Ai-Jun Hou. Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata[J]. Natural Products and Bioprospecting, 2016, 6(1): 25-30.

Lai-Bin Zhang, Chun Lei, Li-Xin Gao, Jing-Ya Li, Jia Li, Ai-Jun Hou. Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata[J]. 应用天然产物, 2016, 6(1): 25-30.

References

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)

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Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

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