Citation: Xiang Yuan, Jianshuang Jiang, Yanan Yang, Xu Zhang, Ziming Feng, Peicheng Zhang. Three quinolizidine dimers from the seeds of Sophora alopecuroides and their hepatoprotective activities[J]. Chinese Chemical Letters, ;2022, 33(6): 2923-2927. doi: 10.1016/j.cclet.2021.10.085 shu

Three quinolizidine dimers from the seeds of Sophora alopecuroides and their hepatoprotective activities

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China

pczhang@imm.ac.cn

Received Date: 31 August 2021
Revised Date: 11 October 2021
Accepted Date: 26 October 2021
Available Online: 2 November 2021

Figures(9)

Sophoralines A-C, three novel [2 + 2] cycloaddition dimers of matrine-based alkaloids with an unprecedented 6/6/6/6/4/6/6/6/6 nonacyclic skeleton containing 11 stereogenic centers, were isolated from Sophora alopecuroides. Their structures were determined by spectroscopic methods, and the absolute configurations were further determined by single-crystal X-ray diffraction analysis for 1 and quantum chemical calculations of electronic circular dichroism (ECD) spectra for 2 and 3. Moreover, 1 exhibited excellent hepatoprotective activities in acetaminophen-induced liver injury in vitro and in vivo.
- Alkaloids,
- Sophora alopecuroides,
- X-ray diffraction,
- Hepatoprotective activities
1. [1]
  C.L. Fan, Y.B. Zhang, Y. Chen, et al., J. Nat. Prod. 82 (2019) 3227-3232. doi: 10.1021/acs.jnatprod.8b01081
2. [2]
  Y.Q. Jia, Z.W. Yuan, X.S. Zhang, et al., J. Ethnopharmacol. 255 (2020) 112775. doi: 10.1016/j.jep.2020.112775
3. [3]
  P. Xiao, J. Li, H. Kubo, et al., Chem. Pharm. Bull. 44 (1996) 1951-1953. doi: 10.1248/cpb.44.1951
4. [4]
  A.U. Atta-Ur-Rahman, M.I. Choudhary, K. Parvez, et al., J. Nat. Prod. 63 (2000) 190-192. doi: 10.1021/np990351v
5. [5]
  J. Kwon, S. Basnet, J.W. Lee, et al., Bioorg. Med. Chem. Lett. 25 (2015) 3314-3318. doi: 10.1016/j.bmcl.2015.05.062
6. [6]
  P.C. Plugge, Arch. Pharm. 233 (1895) 441-443. doi: 10.1002/ardp.18952330608
7. [7]
  Y.B. Zhang, D. Luo, L. Yang, et al., J. Nat. Prod. 81 (2018) 2259-2265. doi: 10.1021/acs.jnatprod.8b00576
8. [8]
  Y.B. Zhang, X.L. Zhang, N.H. Chen, et al., Org. Let. 19 (2017) 424-427. doi: 10.1021/acs.orglett.6b03685
9. [9]
  Y.B. Zhang, L. Yang, D. Lu, et al., Org. Lett. 20 (2018) 5942-5946. doi: 10.1021/acs.orglett.8b02637
10. [10]
  Y. Li, G. Wang, J. Liu, et al., Eur. J. Med. Chem. 188 (2020) 111972. doi: 10.1016/j.ejmech.2019.111972
11. [11]
  Y.X. Huang, G. Wang, J.S. Zhu, et al., Europ. J. Inflam. 14 (2016) 128-132. doi: 10.1177/1721727X16642779
12. [12]
  X. Liu, J. Yang, J. Fu, et al., Org. Lett. 21 (2019) 5753-5756. doi: 10.1021/acs.orglett.9b02166
13. [13]
  Y.B. Zhang, L.Q. Zhan, G.Q. Li, et al., J. Org. Chem. 81 (2016) 6273-6280. doi: 10.1021/acs.joc.6b00804
14. [14]
  M. Bae, J.S. An, E.S. Bae, et al., Org. Lett. 21 (2019) 3635-3639. doi: 10.1021/acs.orglett.9b01057
15. [15]
  W.B. Han, G.Y. Wang, J.J. Tang, et al., Org. Lett. 22 (2020) 405-409. doi: 10.1021/acs.orglett.9b04099
16. [16]
  Y.L. Wang, Y.S. Ye, W.W. Fu, et al., Org. Lett. 21 (2019) 1534-1537. doi: 10.1021/acs.orglett.9b00388
17. [17]
  F.L. Li, S. Lin, S.T. Zhang, et al., Org. Lett. 21 (2019) 8353-8357. doi: 10.1021/acs.orglett.9b03133
18. [18]
  X.M. Chu, C. Wang, W. Liu, et al., Eur. J. Med. Chem. 161 (2019) 101-117. doi: 10.1016/j.ejmech.2018.10.035
19. [19]
  J.B. Xu, H. Zhang, L.S. Gan, et al., J. Am. Chem. Soc. 136 (2014) 7631-7633. doi: 10.1021/ja503995b
20. [20]
  I.S. Movsumov, E.A. Garaev, M.I. Iasev, Chem. Nat. Comp. 42 (2006) 116-117. doi: 10.1007/s10600-006-0054-1
21. [21]
  P.M. Dewick, Medicinal Natural Products: A Biosynthetic Approach. John Wiley & Sons, West Sussex, 2002, pp. 328
1. [1]
  Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
2. [2]
  Wei Li , Guoqiang Feng , Ze Chang . Teaching Reform of X-ray Diffraction Using Synchrotron Radiation in Materials Chemistry. University Chemistry, 2024, 39(3): 29-35. doi: 10.3866/PKU.DXHX202308060
3. [3]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
4. [4]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
5. [5]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
6. [6]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
7. [7]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
8. [8]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
9. [9]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
10. [10]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
11. [11]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
12. [12]
  Xu Zhang , Jiang Li , Kai-Zhou Lu , Ya-Nan Yang , Jian-Shuang Jiang , Xiang Yuan , Zi-Ming Feng , Fei Ye , Pei-Cheng Zhang . Neosophoflavonoids A–C, A class of highly oxidized hybrid flavonoids from Sophora flavescens with antidiabetic effects. Chinese Chemical Letters, 2024, 35(10): 109456-. doi: 10.1016/j.cclet.2023.109456
13. [13]
  Ting Li , Xinxin Zheng , Lejing Qu , Yuanyuan Ou , Sai Qiao , Xue Zhao , Yajun Zhang , Xinfeng Zhao , Qian Li . A chromatographic method for pursuing potential GPCR ligands with the capacity to characterize their intrinsic activities of regulating downstream signaling pathway. Chinese Chemical Letters, 2024, 35(10): 109792-. doi: 10.1016/j.cclet.2024.109792
14. [14]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
15. [15]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
16. [16]
  Yuhang Li , Yang Ling , Yanhang Ma . Application of three-dimensional electron diffraction in structure determination of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100237-100237. doi: 10.1016/j.cjsc.2024.100237
17. [17]
  Chao Ma , Peng Guo , Zhongmin Liu . DNL-16: A new zeolitic layered silicate unraveled by three-dimensional electron diffraction. Chinese Journal of Structural Chemistry, 2024, 43(4): 100235-100235. doi: 10.1016/j.cjsc.2024.100235
18. [18]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
19. [19]
  Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2023.100309
20. [20]
  Shenhao QIU , Qingquan XIAO , Huazhu TANG , Quan XIE . First-principles study on electronic structure, optical and magnetic properties of rare earth elements X (X=Sc, Y, La, Ce, Eu) doped with two-dimensional GaSe. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2250-2258. doi: 10.11862/CJIC.20240104

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(607)
HTML views(54)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142