Abstract
An extensive phytochemical investigation on the roots of Glycyrrhiza uralensis led to the isolation of two new minor chalcone acetylglycosides, i.e., 6″-O-acetylisoliquiritin (1) and 6″-O-acetylneoisoliquiritin (2), including 16 kinds of known constituents (3–18) of flavonoids, chalcones and triterpene saponins. The chemical structures of 1 and 2 were established by spectroscopic analyses of them, particularly by the aid of two-dimensional NMR experiments, COSY, DEPT, HSQC and HMBC. Some isolated components except 1 and 2 exhibited significant inhibitory effects on the proliferation of cultured tumor cell lines, such as A549, SK-OV-3, A-498, and HCD15, in vitro.
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Alejandro, F.B., F.S. Juan, B. Antonio, C. Fernando, and R. Ignacio. 1989. Resorcinol derivatives and other components of Ononis speciosa. Phytochemistry 28: 161–164.
Chen, H.J., S.P. Kang, I.J. Lee, and Y.L. Lin. 2014. Glycyrrhetinic acid suppressed NF-κB activation in TNF-α-induced hepatocytes. Food Chemistry 62: 618–625.
Chen, J., X. Jin, J. Chen, and C. Liu. 2013. Glycyrrhiza poly saccharide induces apoptosis and inhibits proliferation of human hepatocellular carcinoma cells by blocking PI3K/AKT signal pathway. Tumor Biology 34: 1381–1389.
Cheng, A., F. Wan, J. Wang, Z. Jin, and X. Xu. 2008. Macrophage immunomodulatory activity of polysaccharides isolated from Glycyrrhiza uralensis fish. International Immunopharmacology 8: 43–50.
Fu, Y., J. Chen, Y.J. Li, Y.F. Zheng, and P. Li. 2013. Antioxidant and anti-inflammatory activities of six flavonoids separated from licorice. Food Chemistry 141: 1063–1071.
Lee, K.K., O. Yuji, M. Yuzurihara, Y. Kase, and H. Kobayashi. 2013. Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: Role of the active constituents of Glycyrrhizae radix. Journal of Ethnopharmacology 145: 286–293.
Lee, Y.S., S.H. Kim, S.H. Jung, J.K. Kim, C.H. Pan, and S.S. Lim. 2010. Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. Biological & Pharmaceutical Bulletin 33: 917–921.
Li, X., W. Chen, and D. Chen. 2013. Protective effect against hydroxyl-induced DNA damage and antioxidant activity of radix Glycyrrhizae (Liquorice root). Advanced Pharmaceutical Bulletin 3: 167–173.
Marjan, N.A., and H. Hossein. 2008. Review of pharmacological effects of Glycyrrhiza Sp. and its bioactive compounds. Phytotherapy Research 22: 709–724.
Myrna, A., C. Aoki, M. Komoto, L. Deng, I. Shoji, T.S. Wahyuni, M.I. Lusida, Soetjipto, H. Fuchino, N. Kawahara, and H. Hotta. 2014. Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiology and Immunology 58: 180–187.
Shim, S.H., S.Y. Lee, J.S. Kim, K.H. Son, and S.S. Kang. 2005. Norditerpenoid alkaloids and other components from the processed tubers of Aconitum carmichaelii. Archives of Pharmaceutical Research 28: 1239–1243.
Toshio, F., A. Marumo, K. Kaitou, T. Kanda, S. Terada, and T. Nomura. 2002. Antimicrobial activity of licorice flavonoids against methicillin-resistant Staphylococcus aureus. Fitoterapia 73: 536–539.
Tsutomu, H., S. Yasushi, A. Yasuhiro, S. Sumiko, T. Tomofusa, and Y. Takashi. 2000. Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice Phenolics on methicillin-resistant Staphylococcus aureus. Chemical & Pharmaceutical Bulletin 48: 1286–1292.
Yang, N., S. Patil, J. Zhuge, M.C. Wen, J. Bolleddula, S. Doddage, J. Goldfarb, H.A. Sampson, and X.M. Li. 2013. Glycyrrhiza uralensis flavonoids present in anti-asthma formula, ASHMI™, inhibit memory Th2 responses in vitro and in vivo. Phytotherapy Research 27: 1381–1391.
Ye, G., Y.H. Tang, G.X. Xia, Z.L. Sun, Z.X. Li, and C.G. Huang. 2010. Characterization of anti-coxsackie virus B3 Constituents of radix astragali by high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Biomedical Chromatography 24: 1147–1151.
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This research was supported by the basic research Project (KK-1403-C0) of KRICT and also by a Grant of the Technology Innovation Program (10038744) of Korea Evaluation Institute of Industrial Technology (KEIT) funded by Ministry of Trade, Industry & Energy, Republic of Korea.
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Ji Eun Lee and Ji Young Lee contributed equally to this work.
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Lee, J.E., Lee, J.Y., Kim, J. et al. Two minor chalcone acetylglycosides from the roots extract of Glycyrrhiza uralensis . Arch. Pharm. Res. 38, 1299–1303 (2015). https://doi.org/10.1007/s12272-014-0526-y
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DOI: https://doi.org/10.1007/s12272-014-0526-y