Phenanthrenes, anthraquinones, and phenolic constituents from Sinomenium acutum

doi:10.5246/jcps.2017.06.048

Journal of Chinese Pharmaceutical Sciences ›› 2017, Vol. 26 ›› Issue (6): 440-446.DOI: 10.5246/jcps.2017.06.048

• Original articles • Previous Articles Next Articles

Phenanthrenes, anthraquinones, and phenolic constituents from Sinomenium acutum

Haining Lv, Mingbo Zhao, Yong Jiang^*, Pengfei Tu^*

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2017-03-14 Revised:2017-04-23 Online:2017-06-29 Published:2017-05-03
Contact: Tel.: +86-010-82802719; +86-010-82802750, E-mail: yongjiang@bjmu.edu.cn; pengfeitu@bjmu.edu.cn
Supported by:
National Natural Sciences Foundation of China (NSFC; Grant Nos. 81222051 and 81473106), and National Key Technology R&D Program “New Drug Innovation” of China (Grant Nos. 2012ZX09301002-002-002 and 2012ZX09304-005).

Abstract

Abstract:

A phytochemical investigation on the stems and rhizomes of Sinomenium acutum led to the isolation of 19 compounds, including three phenanthrenes, six anthraquinones, and ten phenolic derivatives. The structures of the isolated compounds were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. Compounds 1 and 2 are two new natural products, and their ¹H and ¹³C NMR spectral data were fully assigned for the first time, with the help of 2D NMR. All of the isolates were obtained from genus Sinomenium for the first time and the phenanthrene and anthraquinone are the structure type first reported from this genus plants.

Key words: Sinomenium acutum, Phenanthrenes, Anthraquinones, Phenolic constituents

CLC Number:

R284

Supporting:

Haining Lv, Mingbo Zhao, Yong Jiang, Pengfei Tu . Phenanthrenes, anthraquinones, and phenolic constituents from Sinomenium acutum[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(6): 440-446.

References

[1] Zhao, X.X.; Peng, C.; Zhang, H.; Qin, L.P. Pharm. Biol. 2012, 50, 1053–1061.

[2] Li, H.B. J. Guiyang. Med. Coll. 2006, 31, 154–155.

[3] Zhou, Q.X.; Li, Y.B.; Jiang, J.Q. Pharm. Clin. Res. 2009, 17, 36–38.

[4] Kim, K.H.; Moon, S.R.; Kim, C.S.; Woo, K.W.; Choi, S.U.; Lee, K.R. Biosci. Biotechnol. Biochem. 2013, 77, 2144–2147.

[5] Leigh, W.J.; Lewis, T.J.; Lin, V.; Postigo, J.A. Can. J. Chem. 1996, 74, 263–275.

[6] Goto, K.; Nagai, M. Bull. Chem. Soc. Japan. 1943, 18, 218–220.

[7] Eisenreich, W.J.; Bracher, F. Nat. Prod. Lett. 2001, 15, 147–150.

[8] Mellado, M.; Madrid, A.; Peña-Cortés, H.; López, R.; Jara, C.; Espinoza, L. J. Chil. Chem. Soc. 2013, 58, 1767–1770.

[9] Xu, L.; Chan, C.O.; Lau, C.C.; Yu, Z.; Mok, D.K.; Chen, S. Phytochem. Anal. 2012, 23, 110–116.

[10] Kitanaka, S.; Takido, M. Chem. Pharm. Bull. 1984, 32, 860–864.

[11] Xu, Y.L.; Tang, L.Y.; Zhou, X.D.; Zhou, G.H.; Wang, Z.J. Arch. Pharm. Res. 2015, 38, 1054–1058.

[12] Molander, G.A.; Cavalcanti, L.N. J. Org. Chem. 2011, 76, 623–630.

[13] Yang, C.; Peng, W.; Yang, B.; Zhang, J.; Chen, Y. Nat. Prod. Res. 2016, 30, 1565–1570.

[14] Sribuhom, T.; Sriphana, U.; Thongsri, Y.; Yenjai, C. Phytochem. Lett. 2015, 11, 80–84.

[15] Paredes, A.; Palacios, J.; Quispe, C.; Nwokocha, C.R.; Morales, G.; Kuzmicic, J.; Cifuentes, F. J. Ethnopharmacol. 2016, 192, 99–107.

[16] Camelio, A.M.; Liang, Y.; Eliasen, A.M.; Johnson, T.C.; Yuan, C.; Schuppe, A.W.; Houk, K.N.; Siegel, D. J. Org. Chem. 2015, 80, 8084–8095.

[17] Lancefield, C.S.; Ojo, O.S.; Tran, F.; Westwood, N.J. Angew. Chem. Int. Edit. 2015, 54, 258–262.

[18] Liao, Y.; Niu, X.; Chen, B.; Edwards, H.; Xu, L.; Xie, C.; Lin, H.; Polin, L.; Taub, J.W.; Ge, Y.; Qin, Z. J. Med. Chem. 2016, 59, 7974–7990.

[19] Hahnenkamp, A.; Bremer, C. Bioconjug. Chem. 2013, 24, 1027–1038.

[20] Verotta, L.; Dell’Agli, M.; Giolito, A.; Guerrini, M.; Cabalion, P.; Bosisio, E. J. Nat. Prod. 2001, 64, 603–607.
[21] Hajdu, Z.; Varga, E.; Hohmann, J.; Kalman, A.; Argay, G.; Gunther, G. J. Nat. Prod. 1998, 61, 1298–1299.

Phenanthrenes, anthraquinones, and phenolic constituents from Sinomenium acutum

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 3

Recommended Articles

Metrics

Comments

[1]	Ting Cui, Qixin Zhou, Dan Zhang, Xinhui Jiang. Distribution and pharmacokinetics of five Rhubarb anthraquinones in rabbits and rats [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(2): 115-123.
[2]	Xue Zhang, Jie-Kun Xu, Nai-Li Wang, Hiroshi Kurihara, Xin-Sheng Yao^* . Antioxidant phenanthrenes and lignans from Dendrobium nobile [J]. , 2008, 17(4): 314-318.
[3]	LU Yan-hua, WANG Zheng-tao^*, XU Luo-shan, WU Zi-bin . Three Anthraquinones Isolated from Aster tataricus L.f [J]. , 2003, 12(2): 112-113.