DOI QR코드

DOI QR Code

Terpenoids from Citrus unshiu Peels and Their Effects on NO Production

  • Vu, Thi Oanh (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University) ;
  • Seo, Wonyoung (Department of Biochemistry, College of Natural Sciences, Kangwon National University) ;
  • Lee, Jeong Hyung (Department of Biochemistry, College of Natural Sciences, Kangwon National University) ;
  • Min, Byung Sun (College of Pharmacy, Drug Research and Development Center, Daegu Catholic University) ;
  • Kim, Jeong Ah (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University)
  • Received : 2020.05.11
  • Accepted : 2020.06.14
  • Published : 2020.06.30

Abstract

Two new compounds, 3-methyl-but-2-en-1-yl-1-O-β-xylopyranosyl-(1"→2')-O-β-glucopyranoside (1) and 1-O-β-glucopyranosyl-6-hydroxy-2-methyl-hep-2-enoic acid (2), along with sixteen known terpenoids were isolated from the peels of Citrus unshiu Markov. Their structures were elucidated based on extensive NMR analyses (1H NMR, 13C NMR, DEPT, COSY, HMQC, and HMBC) and high-resolution mass spectrometry. In addition, all isolates (1 - 18) were tested their effects on nitric oxide (NO) production in RAW264.7 cells. Limonin (15) showed to inhibit LPS-induced NO production in a concentration-dependent manner without cytotoxicity.

Keywords

References

  1. Oh, Y. C.; Cho, W. K.; Jeong Y. H.; Im, G. Y.; Yang, M. C.; Hwang, Y. H.; Ma, J. Y. Am. J. Chinese Med. 2012, 40, 611-629. https://doi.org/10.1142/S0192415X12500462
  2. Lim, D. W.; Lee, Y.; Kim, Y. T. Molecules 2014, 19, 783-794. https://doi.org/10.3390/molecules19010783
  3. Moncada, S.; Palmer, R. M.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109-142.
  4. Korhonen, R.; Lahti, A.; Kankaanranta, H.; Moilanen, E. Curr. Drug Targets Inflamm. Allergy 2005, 4, 471-479. https://doi.org/10.2174/1568010054526359
  5. Cao, T. Q.; Tran, M. H.; Kim, J. A.; Tran, P. T.; Lee, J. H.; Woo, M. H.; Lee, H. K.; Min B. S. Bioorg. Med. Chem. Lett. 2015, 25, 5087-5091. https://doi.org/10.1016/j.bmcl.2015.10.020
  6. Chen, H.; Zhou, Y. Z.; Qiao, L.; Cao, J. Q; Yao, Y.; Hua, H. M.; Pei, Y. H. Chem. Pharm. Bull. 2007, 55, 1416-1418. https://doi.org/10.1248/cpb.55.1416
  7. Wu, Y.; Su, J.; Guo, R. X.; Ren, T. K.; Zhang, M.; Dong, M.; Sauriol, F.; Shi, Q.; Gu, Y.; Huo, C. Chem. Nat. Compd. 2014, 50, 603-605. https://doi.org/10.1007/s10600-014-1033-6
  8. Zhang, Z.; Zhang, W.; Ji, Y. P.; Zhao, Y.; Wang, C. G.; Hu, J. F. Phytochemistry 2010, 71, 693-700. https://doi.org/10.1016/j.phytochem.2009.12.017
  9. Kai, H.; Baba, M.; Okuyama, T. Chem. Pharm. Bull. 2007, 55, 133-136. https://doi.org/10.1248/cpb.55.133
  10. Knapp, H.; Weigand, C.; Gloser, J.; Winterhalter, P. J. Agric. Food Chem. 1997, 45, 1309-1313. https://doi.org/10.1021/jf960598n
  11. Yoshikawa, M.; Shimada, H.; Saka, M.; Yoshizumi, S.; Yamahara, J.; Matsuda, H. Chem. Pharm. Bull. 1997, 45, 464-469. https://doi.org/10.1248/cpb.45.464
  12. Kato-Noguchi, H.; Tanaka, Y.; Murakami, T.; Yamamura, S.; Fujihara, S. Phytochemistry 2002, 61, 849-853. https://doi.org/10.1016/S0031-9422(02)00382-5
  13. Li, X.; Yang, M.; Han, Y. F.; Gao, K. Planta Med. 2005, 71, 268-272. https://doi.org/10.1055/s-2005-837827
  14. Nakajima, Y.; Satoh, Y.; Katsumata, M.; Tsujiyama, K.; Ida, Y.; Shoji, J. Phytochemistry 1994, 36, 119-127. https://doi.org/10.1016/S0031-9422(00)97024-9
  15. Perez, J. L.; Jayaprakasha, G.; Valdivia, V.; Munoz, D.; Dandekar, D. V.; Ahmad, H.; Patil, B. S. J. Agric. Food Chem. 2009, 57, 5279-5286. https://doi.org/10.1021/jf803712a
  16. Breksa 3rd, A. P.; Dragull, K.; Wong, R. Y. J. Agric. Food Chem. 2008, 56, 5595-5598. https://doi.org/10.1021/jf800473z
  17. Hasegawa, S.; Bennett, R. D.; Herman, Z.; Fong, C. H.; Ou, P. Phytochemistry 1989, 28, 1717-1720. https://doi.org/10.1016/S0031-9422(00)97831-2
  18. Kim, C.; Ji, J.; Baek, S. H.; Lee, J. H.; Ha, I. J.; Lim, S. S.; Yoon, H. J.; Nam, Y. J.; Ahn, K. S. Pharm. Biol. 2019, 57, 392-402. https://doi.org/10.1080/13880209.2019.1621353
  19. Oh, Y. C.; Cho, W. K.; Jeong, Y. H.; Im, G. Y.; Yang, M. C.; Hwang, Y. H.; Ma, J. Y. Am. J. Chin. Med. 2012, 40, 611-629. https://doi.org/10.1142/S0192415X12500462
  20. Fan, S.; Zhang, C.; Luo, T.; Wang, J.; Tang, Y.; Chen, Z.; Yu, L. Molecules 2019, 24, 3679. https://doi.org/10.3390/molecules24203679
  21. Yang, X. B.; Qian, P.; Yang, X. W.; Liu, J. X.; Gong, N. B.; Yang, L. V. J. Asian Nat. Prod. Res. 2013, 15, 1130-1138. https://doi.org/10.1080/10286020.2013.817392