|
|
|
| (+)-/(—)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head |
| Youzhe Chen, Qinglan Guo, Chengbo Xu, Chenggen Zhu, Jianjun Zhang, Jiangong Shi |
| State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China |
|
|
|
|
Abstract A pair of neolignan enantiomers with an unprecedented carbon skeleton, (+)-/(—)-angelignanine [(+)-/(—)-1], was isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism (CD) exciton chirality method as well as electronic CD quantum calculations. The enantiomers represent the first 2,7'-cyclo-8,9'-neolignans, of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed. In an in vivo test, both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg (i.g.).
|
|
Received: 28 October 2020
|
| Fund: Financial support from the National Natural Sciences Foundation of China (No. 81630094), CAMS Innovation Fund for Medical Science (No. 2017-I2M-3-010) and The Drug Innovation Major Project (No. 2018ZX09711001-001) is acknowledged. |
|
Corresponding Authors:
Jianjun Zhang, Jiangong Shi
E-mail: jjzhang@imm.ac.cn;shijg@imm.ac.cn
|
|
|
|
| [1] |
Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1977, pp. 876-879.
|
| [2] |
I.L.I. Hook, J. Ethnopharm. 152(2014) 1-13.
|
| [3] |
W.L. Wei, R. Zeng, C.M. Gu, Y. Qu, L.F. Huang, J. Ethnopharm. 190(2016) 116-141.
|
| [4] |
J.P. Ma, Z.B. Guo, L. Jin, Y.D. Li, Chin. J. Nat. Med. 13(2015) 241-249.
|
| [5] |
L.B. Zhang, J.L. Lv, J.W. Liu, J. Nat. Prod. 79(2016) 1857-1861.
|
| [6] |
W. Gong, Y. Zhou, X. Li, et al., Molecules 21(2016) 549.
|
| [7] |
L. Zhang, J. Lv, Chem. Nat. Comp. 54(2018) 13-17.
|
| [8] |
J.L. Lv, L.B. Zhang, L.M. Gao, Fitoterapia 129(2018) 102-107.
|
| [9] |
J. Zou, G.D. Chen, H. Zhao, et al., Org. Lett. 20(2018) 884-887.
|
| [10] |
J. Zou, G.D. Chen, H. Zhao, et al., Chem. Commun. 55(2019) 6221-6224.
|
| [11] |
B. Sheng, Y. Vo, P. Lan, et al., Org. Lett. 21(2019) 6295-6299.
|
| [12] |
K. Duric, Y. Liu, S.N. Chen, et al., J. Nat. Prod. 82(2019) 2400-2408.
|
| [13] |
L.J. Meng, Q.L. Guo, C.G. Zhu, et al., Chin. Chem. Lett. 29(2018) 119-122.
|
| [14] |
L. Meng, Q. Guo, M. Chen, et al., Chin. Chem. Lett. 29(2018) 1257-1260.
|
| [15] |
Q. Guo, H. Xia, X. Meng, et al., Acta Pharm. Sin. B 8(2018) 409-419.
|
| [16] |
Q. Guo, C. Xu, M. Chen, et al., Acta Pharm. Sin. B 8(2018) 933-943.
|
| [17] |
Q. Guo, H. Xia, G. Shi, et al., Org. Lett. 20(2018) 816-819.
|
| [18] |
Y. Wu, S. Shao, Q. Guo, et al., Org. Lett. 21(2019) 6850-6854.
|
| [19] |
J. Cai, Q.L. Guo, R.F. Li, et al., Acta Pharm. Sin. 54(2019) 1075-1081.
|
| [20] |
Q. Guo, D. Li, C. Xu, et al., Acta Pharm. Sin. B 10(2020) 895-902.
|
| [21] |
C. Xu, Y. Xin, M. Chen, et al., Eur. J. Med. Chem. 189(2020) 112071.
|
| [22] |
Q. Guo, H. Xia, Y. Wu, et al., Acta Pharm. Sin. B 10(2020) 1954-1965.
|
| [23] |
H. Liu, Y. Wu, Q. Guo, et al., Chin. Chem. Lett. 32(2021) 33-36.
|
| [24] |
K. Nakanishi, N. Berova, The exciton chirality method, in: K. Nakanishi, N. Berova, R.W. Woody (Eds.), Circular Dichroism Principles and Applications, Wiley-VCH, New York, 1994, pp. 361-398.
|
| [25] |
X.C. Li, D. Ferreira, Y.Q. Ding, Curr. Org. Chem. 14(2010) 1678-1697.
|
| [26] |
G.P. Moss, Pure Appl. Chem. 72(2000) 1493-1523.
|
| [27] |
Y. Zhang, M. Li, R.X. Kang, et al., Pharmacol. Biochem. Behav. 102(2012) 450-457.
|
|
|
|
