Regular Article |
|
|
|
|
|
Minor secoiridoid aglycones from the low-polarity part of the traditional Chinese herb: Swertia mileensis |
Chang-An GENG, Xue-Mei ZHANG, Yun-Bao MA, Xiao-Yan HUANG, Ji-Jun CHEN |
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China |
|
|
Abstract Eleven new secoiridoid aglycones involving unusual C9-skeleton:swerimilegenins A-F (1-6); bis-C9-skeleton:swerimilegenin G (7); and C10-skeleton:swerimilegenins H-K (8-11), as well as six known ones, were isolated from the low-polarity part of the traditional Chinese herb medicine Swertia mileensis. Their structures were determined by extensive spectroscopic data and X-ray diffraction. Biogenetically, swerimilegenin A (1) belonged to 10-nor-secoiridoid, and swerimilegenins B-F (2-6) were 1-nor-secoiridoids. Erythrocentaurin (12) and gentiogenal (15) showed moderate anti-HBV activity on HepG 2.2.15 cell line in vitro.
|
Keywords
Swertia mileensis
swerimilegenins
secoiridoid aglycones
anti-HBV activity
|
Fund:This work was funded by the National Natural Science Foundation of China and Yunnan Province (U0832603), the National Science Foundation of China for Distinguished Young Scholars (81025023), the West Light Foundation of the Chinese Academy of Sciences, the International Foundation for Science (No. F/5202-1), and the Youth Innovation Promotion Association, CAS. |
Issue Date: 11 February 2018
|
|
|
[1] |
Boros, C. A.; Stermitz, R. S. J. Nat. Prod. 1990, 53, 1055-1147.
|
[2] |
El-Naggar, L. J.; Beal, J. L. J. Nat. Prod. 1980, 43, 649-707.
|
[3] |
Dinda, B.; Debnath, S.; Harigaya, Y. Chem. Pharm. Bull. 2007, 55, 159-222.
|
[4] |
Jensen, S. R.; Schripsema, J. Gentianaceae-Systematic and Natural History:Gentianaceae-Systematics and Natural History. Cambridge:Cambridge University, 2002; pp 573-630.
|
[5] |
Mulholland, D. A.; Langlois, A.; Randrianarivelojosia, M.; Derat, E.; Nuzillard, J. M. Phytochem. Anal. 2006, 17, 87-90.
|
[6] |
He, K.; Ma, Y. B.; Cao, T. W.; Wang, H. L.; Jiang, F. Q.; Geng, C. A.; Zhang, X. M.; Chen, J. J. Planta Med. 2012, 78, 814-820.
|
[7] |
Wang, H. L.; Geng, C. A.; Ma, Y. B.; Zhang, X. M.; Chen, J. J. Fitoterapia 2013, 89, 183-187.
|
[8] |
Kikuzaki, H.; Kawasaki, Y.; Kitamura, S.; Nakatani, N. Planta Med. 1996, 62, 35-38.
|
[9] |
Li, X. S.; Jiang, Z. Y.; Wang, F. S.; Ma, Y. B.; Zhang, X. M.; Chen, J. J. Chin. J. Chin. Mater. Med. 2008, 33, 2790-2793.
|
[10] |
Zhou, Y.; Di, Y. T.; Gesang, S.; Peng, S. L.; Ding, L. S. Helv. Chim. Acta 2006, 89, 94-102.
|
[11] |
Geng, C. A.; Jiang, Z. Y.; Ma, Y. B.; Luo, J.; Zhang, X. M.; Wang, H. L.; Shen, Y.; Zuo, A. X.; Zhou, J.; Chen J. J. Org. Lett. 2009, 11, 4120-4123.
|
[12] |
Geng, C. A.; Zhang, X. M.; Shen, Y.; Zuo, A. X.; Liu, J. F.; Ma, Y. B.; Luo, J.; Zhou, J.; Jiang, Z. Y.; Chen, J. J. Org. Lett. 2009, 11, 4838-4841.
|
[13] |
Geng, C. A.; Zhang, X. M.; Ma, Y. B.; Jiang, Z. Y.; Luo, J.; Zhou, J.; Wang, H. L.; Chen, J. J. Tetrahedron Lett. 2010, 51, 2483-2485.
|
[14] |
Geng, C. A.; Zhang, X. M.; Ma, Y. B.; Jiang, Z. Y.; Liu, J. F.; Zhou, J.; Chen, J. J. J. Asian Nat. Prod. Res. 2010, 12, 542-548.
|
[15] |
Geng, C. A.; Wang, L. J.; Zhang, X. M.; Ma, Y. B.; Huang, X. Y.; Luo, J.; Guo, R. H.; Zhou, J.; Shen, Y.; Zuo, A. X.; Jiang, Z. Y.; Chen, J. J. Chem. Eur. J. 2011, 17, 3893-3903.
|
[16] |
Geng, C. A.; Zhang, X. M.; Ma, Y. B.; Luo, J.; Chen, J. J. J. Nat. Prod. 2011, 74, 1822-1825.
|
[17] |
Geng, C. A.; Wang, L. J.; Guo, R. H.; Chen, J. J. Mini. Rev. Med. Chem. 2013, 13, 749-776.
|
[18] |
Trost, J. J.; Brown, B. S.; McEachern, E. J.; Kuhn, O. Chem. Eur. J. 2003, 9, 4442-4451.
|
[19] |
Verendel, J. J.; Li, J. Q.; Quan, X.; Peters, B.; Zhou, T. G.; Gautun, O. R.; Govender, T.; Andersson, P. G. Chem. Eur. J. 2012, 18, 6507-6513.
|
[20] |
Takayama, H.; Ishikawa, H.; Kitajima, M.; Aimi, N.; Aji, B. M. Chem. Pharm. Bull. 2004, 52, 359-361.
|
[21] |
Nie, R. L.; He, R. Y. Acta Bot. Yunnan. 1984, 6, 325-328.
|
[22] |
Suhr, J. H.; Arends, P.; Jensen, B. Phytochemistry 1978, 17, 135-138.
|
[23] |
Vander, N. J.; Vander, S. W. G.; Labadie, R. P. Planta Med. 1982, 45, 161-162.
|
[24] |
Cheng, M. J.; Tsai, I. L.; Chen, I. S. J. Chin. Chem. Soc. 2001, 48, 235-239.
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|