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Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

  • Cha, Joon Min (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Kim, Dong Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Lee, Tae Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Subedi, Lalita (Gachon Institute of Pharmaceutical Science, Gachon University) ;
  • Kim, Sun Yeou (Gachon Institute of Pharmaceutical Science, Gachon University) ;
  • Lee, Kang Ro (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
  • Received : 2018.02.07
  • Accepted : 2018.04.02
  • Published : 2018.06.30

Abstract

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.

Keywords

References

  1. Lee, Y. N.; Flora of Korea; Kyohaksa: Korea, 1996; p250.
  2. Song, N.; Xu, W.; Guan, H.; Liu, X.; Wang, Y.; Nie, X. Asian. J. Tradit. Med. 2007, 2, 218-222.
  3. Grosso, C.; Vinholes, J.; Silva, L. R.; de Pinho, P. G.; Gonçalves, R. F.; Valentao, P.; Jager, A. K.; Andrade, P. B. Braz. J. Pharmacog. 2011, 21, 635-644. https://doi.org/10.1590/S0102-695X2011005000107
  4. Selenu, M. B.; Carrus, F.;Bonsignore, L. Boll. Chim. Farm. 2005, 144, 66-78.
  5. Park, C. J.; Park, C. B.; Hong, S. S.; Lee, H. S.; Lee, S. Y.; Kim, S. C. Plant Mol.Biol. 2000, 44, 187-197. https://doi.org/10.1023/A:1006431320677
  6. Kuroda, K.; Akao, M. Jpn. J. Cancer. Res. 1981, 72, 777-782.
  7. Kuroda, K.; Akao, M. Jpn. J. Cancer. Res. 1975, 66, 461-462.
  8. Cha, J. M.; Suh, W. S.; Lee, T. H.; Subedi, L.; Kim, S. Y.; Lee, K. R. Molecules 2017, 22, 1023. https://doi.org/10.3390/molecules22061023
  9. Reif, D. W.; McCreedy, S. A. Arch. Biochem. Biophys. 1995, 320, 170-176. https://doi.org/10.1006/abbi.1995.1356
  10. Batovska, D., I.; Tsubota, S.; Kato, Y.; Asano, Y.; Ubukata, M. Tetrahedron 2004, 15, 3551-3559. https://doi.org/10.1016/j.tetasy.2004.09.033
  11. Wong, H. F.; Brown, G.D. J. Chem. Res. 2002, 5, 30-33.
  12. Duan, H.; Takaishi, Y.; Momota, H.; Ohmoto, Y.; Taki, T. Phytochemistry 2002, 59, 85-90. https://doi.org/10.1016/S0031-9422(01)00429-0
  13. Kimura, J.; Maki, N. J. Nat. Prod. 2002, 65, 57-58. https://doi.org/10.1021/np0103057
  14. Chang, Y. C.; Chang, F. R.; Wu, Y. C. J. Chin. Chem. Soc. 2000, 47, 373-380. https://doi.org/10.1002/jccs.200000050
  15. Achenbach, H.; Stocker, M.; Constenla, M. A. Phytochemistry 1988, 27, 1835-1841. https://doi.org/10.1016/0031-9422(88)80455-2
  16. Kim, J. S.; Kwon, Y. S.; Sa, Y. J.; Kim, M. J. J. Agric. Food. Chem. 2011, 59, 138-144. https://doi.org/10.1021/jf103130a
  17. Kim, D. K.; Lim, J. P.; Kim, J. W.; Park, H. W.; Eun, J. S. Arch. Pharm. Res. 2005, 28, 39-43. https://doi.org/10.1007/BF02975133
  18. Li, Y. L.; Li, J.; Wang, N. L.; Yao, X. S. Molecules 2008, 13, 1931-1941. https://doi.org/10.3390/molecules13081931
  19. Kajjout, M.; Rolando, C. Tetrahedron 2011, 67, 4731-4741. https://doi.org/10.1016/j.tet.2011.03.110
  20. Rayyan, S.; Fossen, T.; Nateland, H. S.; Andersen, O. M. Phytochem. Anal. 2005, 16, 334-341. https://doi.org/10.1002/pca.853
  21. Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem. Int. Ed. 2004, 43, 828-833. https://doi.org/10.1002/anie.200352975
  22. Angles d'Ortoli, T.; Widmalm, G. Tetrahedron 2016, 72, 912-927. https://doi.org/10.1016/j.tet.2015.12.042
  23. Repcak, M.; Imrich, J.; Pihlaja, K.; Kal'atova, M. Phytochemisty 1998, 47, 1219-1221. https://doi.org/10.1016/S0031-9422(97)00713-9

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