Citation: Jingfang Zhang, Xiaoqiang Lei, Yazi Wei, Hui Liu, Qinglan Guo, Tiantai Zhang, Jiangong Shi. Two unique C₂₁-diterpenoid alkaloids from Aconitum carmichaelii[J]. Chinese Chemical Letters, ;2022, 33(12): 5047-5050. doi: 10.1016/j.cclet.2022.03.104 shu

Two unique C₂₁-diterpenoid alkaloids from Aconitum carmichaelii

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

guonina@imm.ac.cn

ttzhang@imm.ac.cn

shijg@imm.ac.cn

Received Date: 26 February 2022
Revised Date: 28 March 2022
Accepted Date: 29 March 2022
Available Online: 1 April 2022

Figures(5)

Two sulfonated diterpenoid alkaloids possessing different but related novel carbon skeletons, named aconidenusulfonine A (1) and 12, 16-secoaconidenusulfonine A (2), respectively, were isolated as minor components from an aqueous extract of the lateral roots of Aconitum carmichaelii ("Fu Zi"). The structures of 1 and 2, representing the first two C₂₁-diterpenoid alkaloids from nature, were determined by analysis of various spectroscopic data and chemical transformation, of which 1 was further proved by single-crystal X-ray diffraction. Especially, 1 exhibited dose-depended analgesic activity consistent with the clinical function of Fu Zi.
- Ranunculaceae,
- Aconitum carmichaelii,
- C₂₁-diterpenoid alkaloid,
- Aconidenusulfonine,
- Analgesic activity
1. [1]
  F.P. Wang, Q.H. Chen, X.Y. Liu, Nat. Prod. Rep. 27 (2010) 529-570. doi: 10.1039/b916679c
2. [2]
  Y. Shen, W.J. Liang, Y.N. Shi, et al., Nat. Prod. Rep. 37 (2020) 763-796. doi: 10.1039/D0NP00002G
3. [3]
  A.M. Thawabteh, A. Thawabteh, F. Lelario, et al., Molecules 26 (2021) 4103. doi: 10.3390/molecules26134103
4. [4]
  R. Chen, G. Sun, Q. Zhang, et al., China J. Chin. Mater. Med. 38 (2013) 1126-1129.
5. [5]
  G. Zhou, L. Tang, X. Zhou, et al., J. Ethnopharmacol. 160 (2015) 173-193. doi: 10.1016/j.jep.2014.11.043
6. [6]
  S. Liu, F. Li, Y. Li, et al., J. Ethnopharmacol. 207 (2017) 237-250. doi: 10.1016/j.jep.2017.06.038
7. [7]
  J.J. Wu, Z.Z. Guo, Y.F. Zhu, et al., Phytomedicine 44 (2018) 187-203. doi: 10.1016/j.phymed.2018.03.001
8. [8]
  M. Yang, X. Ji, Z. Zuo, Toxins 10 (2018) 391. doi: 10.3390/toxins10100391
9. [9]
  B. Jiang, S. Lin, C. Zhu, et al., J. Nat. Prod. 75 (2012) 1145-1159 1878, and 2008.
10. [10]
  Z.B. Jiang, B.Y. Jiang, C.G. Zhu, et al., J. Asian Nat. Prod. Res. 16 (2014) 891-900. doi: 10.1080/10286020.2014.939585
11. [11]
  Z.B. Jiang, X.H. Meng, B.Y. Jiang, et al., Chin. Chem. Lett. 26 (2015) 653-656. doi: 10.1016/j.cclet.2015.04.011
12. [12]
  X.H. Meng, Z.B. Jiang, C.G. Zhu, et al., Chin. Chem. Lett. 27 (2016) 993-1003. doi: 10.1016/j.cclet.2016.05.013
13. [13]
  X.H. Meng, Z.B. Jiang, Q.L. Guo, et al., Chin. Chem. Lett. 28 (2017) 588-592. doi: 10.1016/j.cclet.2016.11.010
14. [14]
  X.H. Meng, Q.L. Guo, C.G. Zhu, et al., Chin. Chem. Lett. 28 (2017) 1705-1710. doi: 10.1016/j.cclet.2017.04.026
15. [15]
  Q. Guo, H. Xia, X. Meng, et al., Acta Pharm. Sin. B 8 (2018) 409-419. doi: 10.1016/j.apsb.2018.03.009
16. [16]
  Q. Guo, H. Xia, G. Shi, et al., Org. Lett. 20 (2018) 816-819. doi: 10.1021/acs.orglett.7b03956
17. [17]
  Y. Wu, S. Shao, Q. Guo, et al., Org. Lett. 21 (2019) 6850-6854. doi: 10.1021/acs.orglett.9b02479
18. [18]
  Q. Guo, H. Xia, Y. Wu, et al., Acta Pharm. Sin. B 10 (2020) 1954-1965. doi: 10.1016/j.apsb.2020.01.013
19. [19]
  H. Liu, Y. Wu, Q. Guo, et al., Chin. Chem. Lett. 32 (2021) 33-36. doi: 10.1016/j.cclet.2020.09.062
20. [20]
  H. Liu, S. Shao, H. Xia, et al., J. Asian Nat. Prod. Res. 23 (2021) 615-626. doi: 10.1080/10286020.2021.1931141
21. [21]
  Z.X. Hu, H.Y. Tang, X.H. Yan, et al., Phytochem. Lett. 29 (2019) 6-11. doi: 10.1016/j.phytol.2018.10.017
22. [22]
  M.N. Sultankhodzhaev, B. Tashkhodzhaev, K.K. Turgunov, et al., Chem. Nat. Compd. 53 (2017) 99-104. doi: 10.1007/s10600-017-1919-1
23. [23]
  F. Zhang, S.L. Peng, X. Liao, et al., Planta Med. 71 (2005) 1073-1076. doi: 10.1055/s-2005-873135
24. [24]
  Z.C. Fan, Z.Q. Zhang, Struct. Chem. 19 (2008) 413-419. doi: 10.1007/s11224-008-9296-9
25. [25]
  T. Okamoto, M. Natsume, Y. Iitaka, et al., Chem. Pharm. Bull. 13 (1965) 1270-1272. doi: 10.1248/cpb.13.1270
26. [26]
  I.M. Yusupova, I.A. Bessonova, B. Tashkodzhaev, Chem. Nat. Compd. 31 (1995) 228-232. doi: 10.1007/BF01170212
27. [27]
  F. Brisse, Acta Cryst. B 27 (1971) 1047-1054.
28. [28]
  L.H. Wright, M. Garynewton, S.W. Pelleti, Chem. Commun. 6 (1970) 359.
29. [29]
  Q. Chen, Experimental Methodology of Pharmacolog, People's Health Press, Beijing, 2010.
1. [1]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
2. [2]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
3. [3]
  Zheng-Biao Zou , Tai-Zong Wu , Chun-Lan Xie , Yuan Wang , Yan Li , Gang Zhang , Rong Chao , Lian-Zhong Luo , Li-Sheng Li , Xian-Wen Yang . neo-Dicitrinols A–C: Unprecedented PKS-NRPS hybrid citrinin dimers with ferroptosis inhibitory activity from the deep-sea-derived Penicillium citrinum W22. Chinese Chemical Letters, 2024, 35(12): 109723-. doi: 10.1016/j.cclet.2024.109723
4. [4]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
5. [5]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
6. [6]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
7. [7]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
8. [8]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
9. [9]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
10. [10]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
11. [11]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
12. [12]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
13. [13]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
14. [14]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
15. [15]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
16. [16]
  Meng Wang , Yan Zhang , Yunbo Yu , Wenpo Shan , Hong He . High-temperature calcination dramatically promotes the activity of Cs/Co/Ce-Sn catalyst for soot oxidation. Chinese Chemical Letters, 2025, 36(1): 109928-. doi: 10.1016/j.cclet.2024.109928
17. [17]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
18. [18]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
19. [19]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
20. [20]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(822)
HTML views(51)

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

Two unique C21-diterpenoid alkaloids from Aconitum carmichaelii

Metrics

通讯作者: 陈斌, bchen63@163.com

Two unique C₂₁-diterpenoid alkaloids from Aconitum carmichaelii