Citation: Meng Xian-Hua, Guo Qing-Lan, Zhu Cheng-Gen, Shi Jian-Gong. Unprecedented C₁₉-diterpenoid alkaloid glycosides from an aqueous extract of "fu zi": Neoline 14-O-L-arabinosides with four isomeric L-anabinosyls[J]. Chinese Chemical Letters, ;2017, 28(8): 1705-1710. doi: 10.1016/j.cclet.2017.04.026 shu

Unprecedented C₁₉-diterpenoid alkaloid glycosides from an aqueous extract of "fu zi": Neoline 14-O-L-arabinosides with four isomeric L-anabinosyls

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

Corresponding author: Shi Jian-Gong, shijg@imm.ac.cn
Received Date: 16 March 2017
Revised Date: 6 April 2017
Accepted Date: 20 April 2017
Available Online: 23 August 2017

Figures(3)

Four structurally unprecedented aconitane-type C₁₉-diterpenoid alkaloid glycosides with isomeric arabinosyls, named aconicarmichosides A-D (1-4), were isolated from an aqueous extract of “fu zi”, the lateral roots of Aconitum carmichaelii. Their structures were determined as neoline 14-O-α-and 14-O-β-L-arabinopyranosides (1 and 2) and 14-O-α-and 14-O-β-L-arabinofuranosides (3 and 4), by spectroscopic and chemical methods including 2D NMR experiments and acid hydrolysis. Compounds 1-4 represent the first examples of glycosidic diterpenoid alkaloids.
- Aconitum carmichaelii,
- Ranunculaceae,
- Fu zi,
- Aconitane alkaloid glycoside,
- Neoline 14-O-L-arabinoside,
- Aconicarmichosides A-D
1. [1]
  Jiangsu New Medical College, A Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1995, pp. 228-2321191-1194.
2. [2]
  Chen Y., Chu Y.L., Chu J.H.. Alkaloids of the Chinese drugs[J]. Aconitum spp. IX. Alkaloids from Chuan-Wu and Fu-Tzu, Aconitum carmichaeli Debx, Acta Pharm. Sin., 1965,12:435-439.
3. [3]
  Iwasa J., Naruto S.. Alkaloids from Aconitum carmichaeli DEBX[J]. J. Pharm. Soc. Jpn., 1966,86:585-590. doi: 10.1248/yakushi1947.86.7_585
4. [4]
  Shim S.H., Lee S.Y., Kim J.S., Son K.H., Kang S.S.. Norditerpenoid alkaloids and other components from the processed tubers of Aconitum carmichaeli[J]. Arch. Pharm. Res., 2005,28:1239-1243. doi: 10.1007/BF02978206
5. [5]
  Konno C., Shirasaka M., Hikino H.. Structure of senbusine A, B and C, diterpenic alkaloids of Aconitum carmichaeli roots from China[J]. J. Nat. Prod., 1982,45:128-133. doi: 10.1021/np50020a003
6. [6]
  Zhang W.D., Han G.Y., Liang H.Q.. Studies on the alkaloid constituents of Jiangyou Fu-zi Aconitum carmichaeli from Sichuan[J]. Acta Pharm. Sin., 1992,27:670-673.
7. [7]
  Wang X.K., Zhao T.F., Lai S.. A new N-formyl C₁₉-diterpenoid alkaloids, aldohypaconitine, from cultivated Aconitum carmichaeli Debx[J]. Chin. Chem. Lett., 1994,5:671-672.
8. [8]
  Xiong J., Gu K., Tan N.H.. Diterpenoid alkaloids from the processed roots of Aconitum carmichaeli[J]. Nat. Prod. Res. Dev., 2008,20:440-443465.
9. [9]
  Liu X.X., Jian X.X., Cai X.F.. Cardioactive C₁₉-diterpenoid alkaloids from the lateral roots of Aconitum carmichaeli "Fu Zi"[J]. Chem. Pharm. Bull., 2012,60:144-149. doi: 10.1248/cpb.60.144
10. [10]
  Gao F., Li Y.Y., Wang D., Huang X., Liu Q.. Diterpenoid alkaloids from the Chinese traditional herbal "Fuzi" and their cytotoxic activity[J]. Molecules, 2012,17:5187-5194. doi: 10.3390/molecules17055187
11. [11]
  Zhang J., Sun G.B., Lei Q.F.. Chemical constituents of lateral roots of Aconitum carmichaelii Debx[J]. Acta Pharm. Sin., 2014,49:1150-1154.
12. [12]
  Zhou G.H., Tang L.Y., Zhou X.D.. A review on phytochemistry and pharmacological activities of the processed lateral root of Aconitum carmichaelii Debeaux[J]. J. Ethnopharm., 2015,160:173-193. doi: 10.1016/j.jep.2014.11.043
13. [13]
  Xu W.D., Tian Y., Guo Q.L., Yang Y.C., Shi J.G.. Secoeuphoractin, a minor diterpenoid with a new skeleton from Euphorbia micractina[J]. Chin. Chem. Lett., 2014,25:1531-1534. doi: 10.1016/j.cclet.2014.09.012
14. [14]
  Tian Y., Guo Q., Xu W.. A minor Diterpenoid with a new 6/5/7/3 fused-ring skeleton from Euphorbia micractina[J]. Org. Lett., 2014,16:3950-3953. doi: 10.1021/ol501760h
15. [15]
  Wang F., Jiang Y.P., Wang X.L.. Aromatic glycosides from the flower buds of Lonicera japonica[J]. J. Asian Nat. Prod. Res., 2013,15:492-501. doi: 10.1080/10286020.2013.785531
16. [16]
  Song W.X., Yang Y.C., Shi J.G.. Two new β-hydroxy amino acid-coupled secoiridoids from the flower buds of Lonicera japonica:isolation, structure elucidation, semisynthesis, and biological activities[J]. Chin. Chem. Lett., 2014,25:1215-1219. doi: 10.1016/j.cclet.2014.05.037
17. [17]
  Jiang Z.B., Song W.X., Shi J.G.. Two new 1-(6'-O-acyl-β-D-glucopyranosyl) pyridinium-3-carboxylates from the flower buds of Lonicera japonica[J]. Chin. Chem. Lett., 2015,26:69-72. doi: 10.1016/j.cclet.2014.10.011
18. [18]
  Yu Y., Jiang Z., Song W.. Glucosylated caffeoylquinic acid derivatives from the flower buds of Lonicera japonica[J]. Acta Pharm. Sin. B, 2015,5:210-214. doi: 10.1016/j.apsb.2015.01.012
19. [19]
  Wang X., Chen M., Wang F.. Chemical constituents from root of Isatis indigotica[J]. Chin. J. Chin. Mater. Med., 2013,38:1172-1182.
20. [20]
  Liu Y.F., Chen M.H., Wang X.L.. Antiviral enantiomers of a bisindole alkaloid with a new carbon skeleton from the roots of Isatis indigotica[J]. Chin. Chem. Lett., 2015,26:931-936. doi: 10.1016/j.cclet.2015.05.052
21. [21]
  Liu Y.F., Chen M.H., Guo Q.L.. Antiviral glycosidic bisindole alkaloids from the roots of Isatis indigotica[J]. J. Asian Nat. Prod. Res., 2015,17:689-704. doi: 10.1080/10286020.2015.1055729
22. [22]
  Liu Y.F., Chen M.H., Lin S.. Indole alkaloid glucosides from the roots of Isatis indigotica[J]. J. Asian Nat. Prod. Res., 2016,18:1-12. doi: 10.1080/10286020.2015.1117452
23. [23]
  Liu Y.F., Wang X.L., Chen M.H.. Three pairs of alkaloid enantiomers from Isatis indigotica[J]. Acta Pharm. Sin. B, 2016,6:141-147. doi: 10.1016/j.apsb.2016.01.003
24. [24]
  M.H. Chen, S. Lin, Y.N. Wang, et al., Antiviral stereoisomers of 3, 5-bis(2-hydroxybut-3-en-1-yl)-1, 2, 4-thiadiazole from the roots Isatis indigotica, Chin. Chem. Lett. 27(2016) 643-648.
25. [25]
  Li D.W., Guo Q.L., Meng X.H.. Two pairs of unusual scalemic enantiomers from Isatis indigotica leaves[J]. Chin. Chem. Lett., 2016,27:1745-1750. doi: 10.1016/j.cclet.2016.08.006
26. [26]
  Liu Y., Chen M., Guo Q.. Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities[J]. ActaPharm. Sin. B, 2017,6:179-184.
27. [27]
  Jiang Y., Liu Y., Guo Q.. Acetylenes and fatty acids from Codonopsis pilosula[J]. Acta Pharm. Sin. B, 2015,5:215-222. doi: 10.1016/j.apsb.2015.03.005
28. [28]
  Jiang Y.P., Liu Y.F., Guo Q.L.. C₁₄-polyacetylene glucosides from Codonopsis pilosula[J]. J. Asian Nat. Prod. Res., 2015,17:601-614. doi: 10.1080/10286020.2015.1041932
29. [29]
  Jiang Y.P., Guo Q.L., Liu Y.F.. Codonopiloneolignanin A, a polycyclic neolignan with a new carbon skeleton from the roots of Codonopsis pilosula[J]. Chin. Chem. Lett., 2016,26:55-58.
30. [30]
  Jiang Y., Liu Y., Guo Q.. Sesquiterpene glycosides from the roots of Codonopsis pilosula[J]. Acta Pharm. Sin. B, 2016,6:46-54. doi: 10.1016/j.apsb.2015.09.007
31. [31]
  Guo Q., Wang Y., Lin S.. 4-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata[J]. Acta Pharm. Sin. B, 2015,5:350-357. doi: 10.1016/j.apsb.2015.02.002
32. [32]
  Guo Q.L., Wang Y.N., Zhu C.G.. 4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata[J]. J. Asian Nat. Prod. Res., 2015,17:439-454. doi: 10.1080/10286020.2015.1040000
33. [33]
  Q.L. Guo, S. Lin, Y.N. Wang, et al., Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of "tian ma":a natural product co-produced by plant and symbiotic fungus, Chin. Chem. Lett. (2016), doi:http://dx.doi.org/10.1016/j.cclet.2016.06.040.
34. [34]
  Jiang B., Lin S., Zhu C.G.. Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii[J]. J. Nat. Prod., 2012,75:1145-11591878. doi: 10.1021/np300225t
35. [35]
  Jiang Z.B., Jiang B.Y., Zhu C.G.. Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii[J]. J. Asian Nat. Prod. Res., 2014,16:891-900. doi: 10.1080/10286020.2014.939585
36. [36]
  Jiang Z.B., Meng X.H., Jiang B.Y.. Two 2-(quinonylcarboxamino)benzoates from the lateral roots of Aconitum carmichaelii[J]. Chin. Chem. Lett., 2015,26:653-656. doi: 10.1016/j.cclet.2015.04.011
37. [37]
  Meng X.H., Jiang Z.B., Zhu C.G.. Napelline-type C₂₀-diterpenoid alkaloid iminiums from "fu zi" and solvent/acid-dependent transformation/equilibration betweeniminium alcohol and aza-acetal forms[J]. Chin. Chem. Lett., 2016,27:993-1003. doi: 10.1016/j.cclet.2016.05.013
38. [38]
  Meng X.H., Jiang Z.B., Guo Q.L., Shi J.G.. A minor arcutine-type C₂₀-diterpenoid alkaloid iminium constituent of "fu zi"[J]. Chin. Chem. Lett., 2017,28:588-592. doi: 10.1016/j.cclet.2016.11.010
39. [39]
  Hikino H., Kuroiwa Y., Konn C.. Structure of hokbusine A and B, diterpenic alkaloids of Aconitum carmichieli roots from Japan[J]. J. Nat. Prod., 1983,46:178-182. doi: 10.1021/np50026a006
40. [40]
  Chen J.. Chemical constituent from radix Aconite Lateralis[J]. Chin. Med. J. Res. Pract., 2013,27:33-35.
41. [41]
  Halabalaki M., Urbain A., Parschali A.. Quercetin and kaempferol 3-O-[α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranoside]-7-O-α-L-rhamnopyranosides from Anthyllis hermanniae:structure determination and conformational studies[J]. J. Nat. Prod., 2011,74:1939-1945. doi: 10.1021/np200444n
42. [42]
  Pelletier S.W., Djarmati Z., Lajsic S., De Camp W.H.. Alkaloids of Delphinium staphisagria. The structure and stereochemistry of delphisine, neoline, chasmanine, and homochasmanine[J]. J. Am. Chem. Soc., 1976,98:2617-2625. doi: 10.1021/ja00425a035
43. [43]
  Pelletier S.W., Djarmati Z.. Carbon-13 nuclear magnetic resonance:aconitinetype diterpenoid alkaloids from Aconitum and Delphinium species[J]. J. Am. Chem. Soc., 1976,98:2626-2636. doi: 10.1021/ja00425a036
44. [44]
  W. Liu, X.J. Gou, Q. Song, F.Z. Chen, Neoline from Aconitum flavum Hand, Acta Cryst. E67(2011) o1435.
45. [45]
  Zhang Z.T., Wang L., Chen Q.F.. Revisions of the diterpenoid alkaloids reported in a JNP paper (2012, 75, 1145-1159)[J]. Tetrahedron, 2013,69:5859-5866. doi: 10.1016/j.tet.2013.05.029
46. [46]
  Wang F.P., Chen D.L., Deng H.Y.. Further revisions on the diterpenoid alkaloids reported in a JNP paper (2012, 75, 1145-1159)[J]. Tetrahedron, 2014,70:2582-2590. doi: 10.1016/j.tet.2014.01.066
47. [47]
  Levrier C., Sadowski M.C., Nelson C.C., Davis R.A.. Cytotoxic C₂₀ diterpenoid alkaloids from the Australian endemic rainforest plant Anopterus macleayanus[J]. J. Nat. Prod., 2015,78:2908-2916. doi: 10.1021/acs.jnatprod.5b00509
48. [48]
  Qu J., Fang L., Ren X.D.. Bisindole alkaloids with neuralanti-inflammatory activity from Gelsemium elegans[J]. J. Nat. Prod., 2013,76:2203-2209. doi: 10.1021/np4005536
49. [49]
  He W.Y., Gao R.M., Li X.Q., Jiang J.D., Li Y.H.. In vitro anti-influenza virus activity of 10 traditional Chinese medicines[J]. Acta Pharm. Sin., 2010,45:395-398.
50. [50]
  F.P. Wang, X.T. Liang, C₂₀-diterpenoid alkaloids, in:G.A. Cordell (Ed.), The Alkaloids:Chemistryand Biology, Elsevier Science, New York, 2002, pp.1-280.
51. [51]
  F.P. Wang, Q.H. Chen, The C₁₉-diterpenoid alkaloids, in:G.A. Cordell (Ed.), The Alkaloids:Chemistry and Biology, Elsevier Science, New York, 2010, pp.1-577.
52. [52]
  F.P. Wang, Q.H. Chen, X.T. Liang, The C₁₈-diterpenoid alkaloids, in:G.A. Cordell (Ed.), The Alkaloids:Chemistry and Biology, Elsevier Science, New York, 2009, pp. 1-78.
53. [53]
  F.P. Wang, Q.H. Chen, X.Y. Liu, Diterpenoid alkaloids, Nat. Prod. Rep. 27(2010) 529-570.
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Unprecedented C19-diterpenoid alkaloid glycosides from an aqueous extract of "fu zi": Neoline 14-O-L-arabinosides with four isomeric L-anabinosyls

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通讯作者: 陈斌, bchen63@163.com

Unprecedented C₁₉-diterpenoid alkaloid glycosides from an aqueous extract of "fu zi": Neoline 14-O-L-arabinosides with four isomeric L-anabinosyls