Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지
DOI QR코드

DOI QR Code

Lignans and Macrolides from the Leaves of Houttuynia cordata with Inhibitory Activity against NO Production in Murine Macrophage RAW 264.7 Cells

  • Ahn, Jongmin (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University) ;
  • Chae, Hee-Sung (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University) ;
  • Chin, Young-Won (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University)
  • Received : 2021.11.30
  • Accepted : 2022.01.13
  • Published : 2022.03.31
Download PDF
⟨ Previous Next ⟩

Abstract

Eight lignans (1-8) and two macrolides (9-10) were isolated from the CHCl3-soluble fraction of Houttuynia cordata Thumb (Saururaceae). Structures of isolates were elucidated by extensive spectroscopic methods. Fatty acid-derived macrolides (9-10) have rarely been reported from nature. All the isolates were tested for their inhibitory activities against NO production in RAW 264.7 cells stimulated by LPS. It was found that compounds 3 and 9 remarkably down-regulated LPS-induced NO production with IC50 values, 5.4 and 40.3 μM, respectively, without cytotoxicity.

Keywords

Acknowledgement

This work was supported by the NRF-2018R1A5 A2023127) from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIT).

References

  1. Kwon, R. H.; Ha, B. J. Toxicol. Res. 2012, 28, 117-122. https://doi.org/10.5487/TR.2012.28.2.117
  2. Chen, S.-D.; Gao, H.; Zhu, Q.-C.; Wang, Y.-Q.; Li, T.; Mu, Z.-Q.; Wu, H.-L.; P eng, T.; Yao, X.-S. Org. Lett. 2012, 14, 1772-1775. https://doi.org/10.1021/ol300017m
  3. Ahn, J.; Chae, H.-S.; Chin, Y.-W.; Kim, J. Bioorg. Med. Chem. Lett. 2017, 27, 2807-2811. https://doi.org/10.1016/j.bmcl.2017.04.072
  4. Bauer, R.; Probstle, A.; Lotter, H.; Wagner-Redecker, W.; Matthiesen, U. Phytomedicine 1996, 2, 305-308. https://doi.org/10.1016/S0944-7113(96)80073-0
  5. Kim, I . S.; Kim, J .-H.; Kim, J . S.; Yun, C .-Y.; K im, D.-H.; L ee, J.-S. J. Ethnopharmacol. 2007, 112, 90-95. https://doi.org/10.1016/j.jep.2007.02.010
  6. Shin, S.; Joo, S. S.; Jeon, J. H.; Park, D.; Jang, M. J.; Kim, T. O.; Kim, H . K.; Hwang, B . Y.; K im, K. Y.; K im, Y. B. J. Vet. Sci. 2010, 11, 273-275. https://doi.org/10.4142/jvs.2010.11.3.273
  7. Hotamisligil, G. S. Nature 2006, 444, 860-867. https://doi.org/10.1038/nature05485
  8. Hopkinson-Woolley, J.; Hughes, D.; Gordon, S.; Martin, P. J. Cell Sci. 1994, 107, 1159-1167. https://doi.org/10.1242/jcs.107.5.1159
  9. Bosca, L.; Zeini, M.; Traves, P. G.; Hortelano, S. Toxicology 2005, 208, 249-258. https://doi.org/10.1016/j.tox.2004.11.035
  10. Vodovotz, Y.; Bogdan, C.; Paik, J.; Xie, Q. W.; Nathan, C. J. Exp. Med. 1993, 178, 605-613. https://doi.org/10.1084/jem.178.2.605
  11. Williams, C. S.; Mann, M.; DuBois, R. N. Oncogene 1999, 18, 7908-7916. https://doi.org/10.1038/sj/onc/1203286
  12. Lee, B. G.; Kim, S. H.; Zee, O. P.; Lee, K. R.; Lee, H. Y.; Han, J. W.; Lee, H. W. Eur. J. Pharmacol. 2000, 406, 301-309. https://doi.org/10.1016/S0014-2999(00)00680-4
  13. Liu, Q.; Wang, J.; Lin, B.; Cheng, Z. Y.; Bai, M.; Shi, S.; Huang, X. X.; Song, S. J. Bioorg. Chem. 2019, 84, 269-275. https://doi.org/10.1016/j.bioorg.2018.11.041
  14. Park, C. H.; Kim, K. H.; Lee, I. K.; Lee, S. Y.; Choi, S. U.; Lee, J. H.; Lee, K. R. Arch. Pharm. Res. 2011, 34, 1289-1296. https://doi.org/10.1007/s12272-011-0808-6
  15. Feng, J.; Hu, M.; Jin, Y. J.; Cao, J. F.; Jia, J. J.; Wang, Y. T.; Li, X. F. Asian J. Chem. 2016, 28, 1820-1822. https://doi.org/10.14233/ajchem.2016.19841
  16. Lundgren, L. N.; Popoff, T.; Theander, O. Phytochemistry 1981, 20, 1967-1969. https://doi.org/10.1016/0031-9422(81)84046-0
  17. Du, J. L.; Jin, Y. S.; Qiao, L. M.; Jin, L.; Chen, H. S. Chem. Nat. Compd. 2010, 46, 459-461. https://doi.org/10.1007/s10600-010-9644-z
  18. Xie, L.-H.; Akao, T.; Hamasaki, K.; Deyama, T.; Hattori, M. Chem. Pharm. Bull (Tokyo). 2003, 51, 508-515. https://doi.org/10.1248/cpb.51.508
  19. Jutiviboonsuk, A.; Zhang, H.; Tan, G. T.; Ma, C.; Van Hung, N.; Cuong, N. M.; Bunyapraphatsara, N.; Soejarto, D. D.; Fong, H. H. S. Phytochemistry 2005, 66, 2745-2751. https://doi.org/10.1016/j.phytochem.2005.09.025
  20. Gan, M.; Zhang, Y.; Lin, S.; Liu, M.; Song, W.; Zi, J.; Yang, Y.; Fan, X.; Shi, J.; Hu, J.; Sun, J.; Chen, N. J. Nat. Prod. 2008, 71, 647-654. https://doi.org/10.1021/np7007329
  21. Zeng, Q .; Ye, J .; R en, J.; Cheng, X .; Q in, J.; Jin, H . Z.; Zhang, W. D. Chem. Nat. Compd. 2013, 49, 486-492. https://doi.org/10.1007/s10600-013-0644-7
  22. Matsushita, K.; Sanada, M. Physiol. Plant Pathol. 1978, 13, 365-368. https://doi.org/10.1016/0048-4059(78)90053-x
  23. Schulz, S.; Yildizhan, S.; Stritzke, K.; Estrada, C.; Gilbert, L. E. Org. Biomol. Chem. 2007, 5, 3434-3441. https://doi.org/10.1039/b710284d
  24. Kim, N.-H.; Yang, M. H.; Heo, J.-D.; Sung, S. H.; Jeong, E. J. Nat. Prod. Sci. 2016, 22, 53-59. https://doi.org/10.20307/nps.2016.22.1.53
  25. Phillips, B. E.; Smith, C. R. J.; Tjarks, L. W. J. Org. Chem. 1970, 35, 1916-1919. https://doi.org/10.1021/jo00831a043
  26. Miyakado, M.; Meinwald, J.; Gilbert, L. E. Experientia 1989, 45, 1006-1008. https://doi.org/10.1007/BF01953063
  27. Lee, J.; Choi, J.; Kim, S. Br. J. Pharmacol. 2015, 172, 3353-3369. https://doi.org/10.1111/bph.13137
  28. Choi, G.; Han, A. R.; Lee, J. H.; Park, J. Y.; Kang, U.; Hong, J.; Kim, Y. S.; Seo, E. K. Chem. Biodivers. 2015, 12, 380-387. https://doi.org/10.1002/cbdv.201400242
  29. Tsuneyoshi, T.; Kanamori, Y.; Matsutomo, T.; Morihara, N. Biochem. Biophys. Res. Commun. 2015, 465, 408-413. https://doi.org/10.1016/j.bbrc.2015.08.020
  30. Liu, S.-Y.; Xu, P.; Luo, X.-L.; Hu, J.-F.; Liu, X.-H. Neurochem. Res. 2016, 41, 1570-1577. https://doi.org/10.1007/s11064-016-1870-8
  31. Lee, W.; Ko, K. R.; Kim, H. K.; Lim, S.; Kim, S. Biochem. Biophys. Res. Commun. 2018, 495, 2242-2248. https://doi.org/10.1016/j.bbrc.2017.12.079