Citation: Hui Liu, Yuzhuo Wu, Qinglan Guo, Shuai Shao, Chengbo Xu, Tiantai Zhang, Jiangong Shi. Aconapelsulfonines A and B, seco C20-diterpenoid alkaloids deriving via Criegee rearrangements of napelline skeleton from Aconitum carmichaelii[J]. Chinese Chemical Letters, ;2021, 32(1): 33-36. doi: 10.1016/j.cclet.2020.09.062 shu

Aconapelsulfonines A and B, seco C20-diterpenoid alkaloids deriving via Criegee rearrangements of napelline skeleton from Aconitum carmichaelii

    * Corresponding authors.
    E-mail addresses: ttzhang@imm.ac.cn (T. Zhang), shijg@imm.ac.cn (J. Shi).
    1 These authors contributed equally to this work.
  • Received Date: 4 August 2020
    Revised Date: 8 September 2020
    Accepted Date: 30 September 2020
    Available Online: 1 October 2020

Figures(5)

  • Two sulfonated seco C20-diterpenoid alkaloids, aconapelsulfonines A (1) and B (2), were isolated from an aqueous extract of the raw material of "Fu Zi" (the Aconitum carmichaelii lateral roots), of which the structures were elucidated by various spectroscopic data, combined with X-ray crystallographic analysis. The unprecedented skeletons are biogenetically proposed to be derived via Criegee rearrangements of the napelline-type architecture. The two compounds exhibited dose-depended analgesic activities on an acetic acid-induced mice writhing test.
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    1. [1]

      (a) X.Y. Liu, Y. Qin, Nat. Prod. Rep. 34 (2017) 1044-1050;
      (b) J.J. Pflueger, L.C. Morrill, J.N. deGruyter, et al., Org. Lett. 19 (2017) 4632-4635;
      (c) Y. Nishiyama, S. Yokoshina, T. Fukuyama, Org. Lett. 19 (2017) 5833-5835;
      (d) K.G.M. Kou, J.J. Pflueger, T. Kiho, et al., J. Am. Chem. Soc. 140 (2018) 8105-8109;
      (e) S. Zhou, R. Guo, P. Yang, et al., J. Am. Chem. Soc. 140 (2018) 9025-9029;
      (f) N.A. Doering, K.G.M. Kou, K. Norseeda, et al., J. Org. Chem. 83 (2018) 12911-12920;
      (g) Q.Z. Zhang, Z.S. Zhang, Z. Huang, et al., Angew. Chem. Int. Ed. 57 (2018) 937-941;
      (h) J. Liu, D. Ma, Angew. Chem. Int. Ed. 57 (2018) 6676-6680;
      (i) S. Xie, G. Chen, H. Yan, et al., J. Am. Chem. Soc. 141 (2019) 3435-3439;
      (j) W. Nie, J. Gong, Z. Chen, et al., J. Am. Chem. Soc. 141 (2019) 9712-9718;
      (k) L. Zou, K. Yu, Y. Fan, et al., ACS Chem. Neurosci. 10 (2019) 1318-1325;
      (l) S. Shao, H. Xia, M. Hu, et al., J. Neuroinflam. 17 (2020) 13.

    2. [2]

      (a) F.P. Wang, Q.H. Chen, X.Y. Liu, Nat. Prod. Rep. 27 (2010) 529-570;
      (b) Z.Q. Mu, H. Gao, Z.Y. Huang, et al., Org. Lett. 14 (2012) 2758-2761;
      (c) J.F. Zhang, L. Chen, S. Huang, et al., J. Nat. Prod. 80 (2017) 3136-3142.

    3. [3]

      (a) R. Chen, G. Sun, Q. Zhang, et al., China J. Chin. Mater. Med. 38 (2013) 1126-1129;
      (b) S. Liu, F. Li, Y. Li, et al., J. Ethnopharmacol. 207 (2017) 237-250;
      (c) J. Wu, Z. Guo, Y. Zhu, et al., Phytomedicine 44 (2018) 187-203;
      (d) M. Yang, X. Ji, Z. Zou, Toxins 10 (2018) 391.

    4. [4]

      (a) L. Wang, J.Y. Ding, X.X. Liu, et al., Acta Pharm. Sin. 49 (2014) 1699-1704;
      (b) G. Zhou, L. Tang, X. Zhou, et al., J. Ethnopharm. 160 (2015) 173-193;
      (c) X. Zong, X. Yan, J.L. Wu, et al., J. Nat. Prod. 82 (2019) 980-989;
      (d) Y.Y. Zhu, G. Yu, Y.Y. Wang, et al., Chem. Nat. Comp. 55 (2019) 189-193;
      (e) W. Xu, M. Zhang, H. Liu, et al., Nat. Prod. Res. 33 (2019) 1486-1490;
      (f) T.Q. Do, B.N. Truong, H.D.T. Mai, et al., J. Asian Nat. Prod. Res. 21 (2019) 507-515.

    5. [5]

      (a) Q. Guo, C. Xu, M. Chen, et al., Acta Pharm. Sin. B 8 (2018) 933-943;
      (b) L.J. Meng, Q.L. Guo, C.G. Zhu, et al., Chin. Chem. Lett. 29 (2018) 119-122;
      (c) L. Meng, Q. Guo, M. Chen, et al., Chin. Chem. Lett. 29 (2018) 1257-1260;
      (d) Q. Guo, D. Li, C. Xu, et al., Acta Pharm. Sin. B 10 (2020) 895-902.

    6. [6]

      (a) B. Jiang, S. Lin, C. Zhu, et al., J. Nat. Prod. 75 (2012) 1145-1159 1878, and 2008;
      (b) Z.B. Jiang, B.Y. Jiang, C.G. Zhu, et al., J. Asian Nat. Prod. Res. 16 (2014) 891-900;
      (c) Z.B. Jiang, X.H. Meng, B.Y. Jiang, et al., Chin. Chem. Lett. 26 (2015) 653-656;
      (d) X.H. Meng, Z.B. Jiang, C.G. Zhu, et al., Chin. Chem. Lett. 27 (2016) 993-1003;
      (e) X.H. Meng, Z.B. Jiang, Q.L. Guo, et al., Chin. Chem. Lett. 28 (2017) 588-592;
      (f) X.H. Meng, Q.L. Guo, C.G. Zhu, et al., Chin. Chem. Lett. 28 (2017) 1705-1710;
      (g) Q. Guo, H. Xia, G. Shi, et al., Org. Lett. 20 (2018) 816-819;
      (h) Q. Guo, H. Xia, X. Meng, et al., Acta Pharm. Sin. B 8 (2018) 409-419;
      (i) Y. Wu, S. Shao, Q. Guo, et al., Org. Lett. 21 (2019) 6850-6854;
      (j) Q. Guo, H. Xia, Y. Wu, et al., Acta Pharm. Sin. B 10 (2020) 1954-1965.

    7. [7]

      Q. Chen, Experimental Methodology of Pharmacolog, People's Health Press, Beijing, 2010.

    8. [8]

      (a) I. Polyak, M.T. Reetz, W. Thiel, J. Am. Chem. Soc. 134 (2012) 2732-2741;
      (b) B.J. Yachnin, T. Sprule, M.B. McEvoy, et al., J. Am. Chem. Soc. 134 (2012) 7788-7795;
      (c) G. Li, M. Garcia-Borras, M.J.L.J. Furst, et al., J. Am. Chem. Soc. 140 (2018) 10464-10472.

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