A minor arcutine-type C20-diterpenoid alkaloid iminium constituent of "fu zi"
- Corresponding author: Shi Jian-Gong, shijg@imm.ac.cn
Citation:
Meng Xian-Hua, Jiang Zhi-Bo, Guo Qing-Lan, Shi Jian-Gong. A minor arcutine-type C20-diterpenoid alkaloid iminium constituent of "fu zi"[J]. Chinese Chemical Letters,
;2017, 28(3): 588-592.
doi:
10.1016/j.cclet.2016.11.010
Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Publishing House, Shanghai, 1995, pp. 228-2321191-1194. (in Chinese).
Konno C., Shirasaka M., Hikino H.. Structure of senbusine A, B and C, diterpenie alkaloids of Aconitum carmichaelii roots from China[J]. J. Nat. Prod., 1982,45:128-133. doi: 10.1021/np50020a003
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 carmichaelii[J]. Arch. Pharm. Res., 2005,28:1239-1243. doi: 10.1007/BF02978206
Liu X.X., Jian X.X., Cai X.F.. Cardioactive C19-diterpenoid alkaloids from the lateral roots of Aconitum carmichaelii fu zi[J]. Chem. Pharm. Bull., 2012,60:144-149. doi: 10.1248/cpb.60.144
Gao F., Li Y.Y., Wang D., Huang X., Liu Q.. Diterpenoid alkaloids fromthe Chinese traditional herbal fu zi and their cytotoxic activity[J]. Molecules, 2012,17:5187-5194. doi: 10.3390/molecules17055187
Xiong L., Peng C., Xie X.F.. Alkaloids isolated from the lateral root of Aconitum carmichaelii[J]. Molecules, 2012,17:9939-9946. doi: 10.3390/molecules17089939
Wang L., Ding J.Y., Liu X.X.. Identification of aminoalcohol-diterpenoid alkaloids in Aconiti Lateralis Radix Praeparata and study of their cardiac effects[J]. Acta Pharm. Sin., 2014,49:1699-1704.
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.
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. Ethnopharmcol., 2015,160:173-193. doi: 10.1016/j.jep.2014.11.043
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 carmichaelii Debx, Acta Pharm. Sin., 1965,12:435-439.
Iwasa J., Naruto S.. Alkaloids from Aconitum carmichaeliiDebx[J]. Yakugaku Zasshi, 1966,86:585-590.
Wang X.K., Zhao T.F., Lai S.. A new N-formyl C19-diterpenoid alkaloid aldohypaconitine, from the cultivated Aconitum carmichaelii, Debx[J]. Chin. Chem. Lett., 1994,5:671-672.
Xiong J., Gu K., Tan N.H.. Diterpenoid alkaloids from the processed roots of Aconitum carmichaelii[J]. Nat. Prod. Res. Dev., 2008,20:440-443465.
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
Tian Y., Guo Q.L., Xu W.D.. A minor diterpenoid with a new 6/5/7/3 fusedring skeleton from Euphorbia micractina[J]. Org. Lett., 2014,16:3950-3953. doi: 10.1021/ol501760h
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
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
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
Yu Y., Jiang Z.B., Song W.X.. 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
Wang X.L., Chen M.H., Wang F.. Chemical consitituents from root of Isatis indigotica[J]. China J. Chin. Mater. Med., 2013,38:1172-1182.
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
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
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
Liu Y.F., Wang X.L., Chen M.H.. Three pairs of alkaloid enantiomers from the root of Isatis indigotica[J]. Acta Pharm. Sin. B, 2016,6:141-147. doi: 10.1016/j.apsb.2016.01.003
Chen M.H., Lin S., Wang Y.N.. Antiviral stereoisomers of 3, 5-bis (2-hydroxybut-3-en-1-yl)-1, 2, 4-thiadiazole from the roots Isatis indigotica[J]. Chin. Chem. Lett., 2016,27:643-648. doi: 10.1016/j.cclet.2016.01.042
Jiang Y.P., Liu Y.F., Guo Q.L.. Acetylenes and fatty acids from Codonopsis pilosula[J]. Acta Pharm. Sin. B, 2015,5:215-222. doi: 10.1016/j.apsb.2015.03.005
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
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., 2016,27:55-58. doi: 10.1016/j.cclet.2015.11.009
Jiang Y.P., Liu Y.F., Guo Q.L.. 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
Guo Q.L., Wang Y.A., 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
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
Guo Q.L., Lin S., Wang Y.N.. Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of tian ma:a natural product co-produced by plant and symbiotic fungus[J]. Chin. Chem. Lett., 2016,27:1577-1581. doi: 10.1016/j.cclet.2016.06.040
Jiang B.Y., Lin S., Zhu C.G.. Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii[J]. J. Nat. Prod., 2012,75:1145-1159. doi: 10.1021/np300225t
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
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
Meng X.H., Jiang Z.B., Zhu C.G.. Napelline-type C20-diterpenoid alkaloid iminiums from an aqueous extract of fu zi:solvent-/base-/acid-dependent transformation and equilibration between alcohol iminium and aza acetal forms[J]. Chin. Chem. Lett., 2016,27:993-1003. doi: 10.1016/j.cclet.2016.05.013
Tashkhodzhaev B., Saidkhodzhaeva S.A., Bessonova I.A., Antipin M.Y.. Arcutin-a new type of diterpene alkaloids[J]. Chem. Nat. Compd., 2000,36:79-83. doi: 10.1007/BF02234909
Saidkhodzhaeva S.A., Bessonova I.A., Abdullaev N.D.. Arcutinine, a newalkaloid from Aconitum arcuatum[J]. Chem. Nat. Compd., 2001,37:466-469. doi: 10.1023/A:1014479628541
Wang F.P., Chen Q.H., Liu X.Y.. Diterpenoid alkaloids[J]. Nat. Prod. Rep, 2010,27:529-570. doi: 10.1039/b916679c
Pelletier S.W., Mody N.V.. Developments in the chemistry of diterpenoid alkaloids[J]. J. Nat. Prod., 1980,43:41-71. doi: 10.1021/np50007a003
F.P. Wang, X.T. Liang, in:G.A. Cordell (Ed.), The Alkaloids:Chemistry and Pharmacology, vol. 42, Academic Press, New York, 1992, pp. 151-248.
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
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
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
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