Citation: Liu Rui, Zou Hui, Xu Ping-Sheng, Zou Zhen-Xing, Li Jing, Cheng Fei, Liu Rui-Huan, Zhou Gan, Xu Kang-Ping, Tan Gui-Shan. Uncinatic acids A-C, three new carboxylated flavonoids from Selaginella uncinata[J]. Chinese Chemical Letters, ;2017, 28(7): 1465-1468. doi: 10.1016/j.cclet.2017.03.004 shu

Uncinatic acids A-C, three new carboxylated flavonoids from Selaginella uncinata

Liu Rui ^a,b ,
Zou Hui ^a,b ,
Xu Ping-Sheng ^a ,
Zou Zhen-Xing ^a ,
Li Jing ^b ,
Cheng Fei ^a ,
Liu Rui-Huan ^b ,
Zhou Gan ^a ,
Xu Kang-Ping ^b ,
Tan Gui-Shan ^a,b,*,,

a.
Xiangya Hospital of Central South University, Changsha 410008, China
b.
Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, China

Corresponding author: Tan Gui-Shan, tgs395@aliyun.com

Received Date: 30 November 2016
Revised Date: 18 January 2017
Accepted Date: 21 February 2017
Available Online: 9 July 2017

Figures(2)

Three new carboxylated flavonoids, uncinatic acids A-C (1-3), were isolated from the whole herb of Selaginella uncinata. Their structures were established on the basis of extensive NMR analysis including 1D, 2D NMR experiments and HR-ESIMS techniques. All of them share the carboxylation structural characteristic. Compounds 1 and 2 belong to novel naturally occuring furanoflavonoids which is firstly reported in genus Selaginella. Such furanoflavonoids with dicarboxylic acid structrure have never been discovered before. In addition, the isolates were tested for their cytotoxicity against A549 and BGC-823 cell lines in vitro.
- Selaginella uncinata,
- Selaginella,
- Uncinatic acids A-C,
- Carboxylated flavonoids,
- Furanoflavonoids,
- Anticancer,
- Cytotoxicity
1. [1]
  Jiangsu New Medical College, Dictionary of Chinese Materia Medica, Shanghai Scientific and Technic Press. 19861472.
2. [2]
  Zou H., Xu K.P., Liu R.. Selacyclicbiflavone A, an unusual macrocyclic biflavone from Selaginella uncinata (Desv.) Spring[J]. Tetrahedron Lett., 2016,57:892-894. doi: 10.1016/j.tetlet.2016.01.038
3. [3]
  Zou H., Xu K.P., Li F.S.. Unciflavones A-F, six novel flavonoids from Selaginella uncinata (Desv.) Spring[J]. Fitoterapia, 2014,99:328-333. doi: 10.1016/j.fitote.2014.10.012
4. [4]
  Zou H., Yi M.L., Xu K.P.. Two new flavonoids from Selaginella uncinata[J]. J. Asian Nat. Prod. Res., 2016,18:248-252. doi: 10.1080/10286020.2015.1063617
5. [5]
  Zhen J.X., Wang N.L., Gao H.. A new flavonoid with a benzoic acid substituent from Selaginella uncinata[J]. Chin. Chem. Lett., 2008,19:1093-1095. doi: 10.1016/j.cclet.2008.06.024
6. [6]
  Zheng J.X., Wang N.L., Liu H.W.. Four new biflavonoids from Selaginella uncinata and their anti-anoxic effect[J]. J. Asian Nat. Prod. Res., 2008,10:945-952. doi: 10.1080/10286020802181166
7. [7]
  Zheng J.X., Zheng Y., Zhi H.. New 3', 8''-linked biflavonoids from Selaginella uncinata displaying protective effect against anoxia[J]. Molecules, 2011,16:6206-6214. doi: 10.3390/molecules16086206
8. [8]
  Ma L.Y., Ma S.C., Feng W.. Uncinoside A and B, two new antiviral chromone glycosides from Selaginella uncinata[J]. Chem. Pharm. Bull., 2003,51:1264-1267. doi: 10.1248/cpb.51.1264
9. [9]
  Zheng J.X., Zheng Y., Zhi H.. Two new steroidal saponins from Selaginella uncinata (Desv.) Spring and their protective effect against anoxia[J]. Fitoterapia, 2013,88:25-30. doi: 10.1016/j.fitote.2013.04.003
10. [10]
  Zou Z.X., Tan G.S., Zhang G.G.. New cytotoxic apigenin derivatives from Selaginella doederleinii[J]. Chin. Chem. Lett., 2017,28. doi: 10.1016/j.cclet.2017.01.011
11. [11]
  Wang S.Q., Zhang Q.W., Wang X.L.. Chemical constituents from Cicuta virosa Linnaeus and their reversal effects on doxorubicin-resistant human myelogenous leukemia (K562/A02) cells[J]. Chin. Chem. Lett., 2016,27:1013-1016. doi: 10.1016/j.cclet.2016.03.039
12. [12]
  Wang X.L., Di X.X., Shen T.. New phenolic compounds from the leaves of Artocarpus heterophyllus[J]. Chin. Chem. Lett., 2017,28:37-40. doi: 10.1016/j.cclet.2016.06.024
13. [13]
  Su Q.L., Peng M., Zhang Y.. Quercetin induces bladder cancer cells apoptosis by activation of AMPK signaling pathway[J]. Am. J. Cancer. Res., 2016,6:498-508.
14. [14]
  Slade D., Ferreira D., Marais J.P.J.. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids[J]. Phytochemistry, 2005,66:2177-2215. doi: 10.1016/j.phytochem.2005.02.002
15. [15]
  Banks J.A., Nishiyama T., Hasebe M.. The Selaginella genome identifies genetic changes associated with the evolution of vascular plants[J]. Science, 2011,332:960-963. doi: 10.1126/science.1203810
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沈阳化工大学材料科学与工程学院沈阳 110142