DOI QR코드

DOI QR Code

Chemical Constituents from the Aerial Parts of Vernonia cinerea L. and Their Anti-Inflammatory Activity

베르노니아 시네레아 지상부의 화학 성분 및 항염증 활성

  • Youn, Ui Joung (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Chang, Leng Chee (Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawaii)
  • 윤의중 (극지연구소 극지생명과학연구부) ;
  • 장영기 (하와이주립대학교 약학대학)
  • Received : 2016.10.05
  • Accepted : 2016.12.12
  • Published : 2016.12.30

Abstract

Background: Previous phytochemical studies of whole Vernonia cinerea L. plants have identified sesquiterpene lactones, sterols, and triterpenes, which possess anticancer, antifeedant, and antimalarial activities. However, there are no reports of other types of bioactive metabolites. Therefore, the present study aimed to identify phenolic compounds with anti-inflammatory activity in the aerial parts of the plant. Methods and Results: Compounds were isolated from the aerial parts of V. cinerea using a silica and C-18 gel columns and semi-preparative HPLC instrument, and the structures of the compounds were determined using one- and two- dimension nuclear magnetic resonance spectroscopy and mass spectroscopy. The chloroform soluble extracts and isolated compounds were evaluated for their anti-inflammatory potential based on their ability to inhibit nitric oxide production and $TNF-{\alpha}$ induced $NF-{\kappa}B$ activity. Conclusions: Phytochemical study of the aerial parts of V. cinerea led to the isolation of six phenolic compounds. Compound 1 was a major metabolite, and to the best of our knowledge, compounds 2 - 6 were isolated from V.cinerea for the first time. Among the isolates, compounds 1 and 3 exhibited $TNF-{\alpha}$-induced $NF-{\kappa}B$ activity with $IC_{50}$ values of 7.5 and 11.5 M, respectively, and the inhibitory activity of phenyl propanoid compound 3 on $TNF-{\alpha}$-induced $NF-{\kappa}B$ was evaluated for the first time.

Keywords

References

  1. Anggard E. (1994). Nitric oxide: Mediator, murderer, and medicine. Lancet. 343:1199-1206. https://doi.org/10.1016/S0140-6736(94)92405-8
  2. Baldwin AS. (2001). Control of oncogenesis and cancer therapy resistance by the transcription factor NF-${\kappa}B$. Journal of Clinical Investigation. 107:241-246. https://doi.org/10.1172/JCI11991
  3. Beeran AA, Maliyakkal N, Rao CM and Udupa N. (2014). The enriched fraction of Vernonia cinerea L. induces apoptosis and inhibits multi-drug resistance transporters in human epithelial cancer cells. Journal of Ethnopharmacology. 158:33-42. https://doi.org/10.1016/j.jep.2014.10.010
  4. Balasundram N, Sundram K and Samman S. (2006). Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chemistry. 99:191-203. https://doi.org/10.1016/j.foodchem.2005.07.042
  5. Chea A, Hout S, Long C, Marcourt L, Faure R, Azas N and Elias R. (2006). Antimalarial activity of sesquiterpene lactones from Vernonia cinerea. Chemical and Pharmaceutical Bulletin. 54:1437-1439. https://doi.org/10.1248/cpb.54.1437
  6. Choi YH, Kim JH, Kim MJ, Han SS and Rim YS. (2000). Antioxidative compounds in leaves of Castanea crenata S. et Z. Korean Journal of Medicinal Crop Sciences. 8:373-377.
  7. Dastur JF. (1977). Medicinal plants of India and Pakistan. D.B Taraporevala Sons and Co., Ltd. Maharashtra, India. p.174.
  8. Davidse PA, Dillen JLM, Heyns AM, Modro TA and Rooyen PHV. (1990). Photochromic systems. Part 1. Structural and spectroscopic study of photochromically active products of Stobbe condensation. 2,3-Dibenzylidenesuccinic acid and its anhydride. Canadian Journal of Chemistry. 68:741-746. https://doi.org/10.1139/v90-117
  9. Han JT, Bang MH, Chun OK, Kim DO, Lee CY and Baek NI. (2004). Flavonol glycosides from the aerial parts of Aceriphyllum rossii and their antioxidant activities. Archives of Pharmacal Research. 27:390-395. https://doi.org/10.1007/BF02980079
  10. Jones L, Bartholomew B, Latif Z, Sarker SD and Nash RJ. (2000). Constituents of Cassia laevigata. Fitoterapia. 71:580-583. https://doi.org/10.1016/S0367-326X(00)00155-6
  11. Kim BH, Choi JS, Yi EH, Lee JK, Won C, Ye SK and Kim MH. (2013). Relative antioxidant activities of quercetin and its structurally related substances and their effects on NF-${\kappa}B$/ CRE/AP-1 signaling in murine macrophages. Molecules and Cells. 35:410-420. https://doi.org/10.1007/s10059-013-0031-z
  12. Kirtikar KR, Basu BD and an I.C.S. (1975). Indian medicinal plants. Bishen Singh Mahendra Pal Singh. Dehradun, India. p.1322.
  13. Kitajima J, Ishikawa T, Tanaka T and Ida Y. (1999). Watersoluble constituents of fennel. IX. Glucides and nucleosides. Chemical and Pharmaceutical Bulletin. 47:988-992. https://doi.org/10.1248/cpb.47.988
  14. Kondratyuk TP, Park EJ, Yu R, van Breemen RB, Asolkar RN, Murphy BT, Fenical W and Pezzuto JM. (2012). Novel marine phenazines as potential cancer chemopreventive and anti-inflammatory agents. Marine Drugs. 10:451-464. https://doi.org/10.3390/md10020451
  15. Kone WM and Kande B. (2012). Qualitative analysis of the pyrrolizidine alkaloids from 11 Asteraceae and Boraginaceae used in traditional medicine in Cote d'Ivoire. Research Journal of Phytochemistry. 6:75-83. https://doi.org/10.3923/rjphyto.2012.75.83
  16. Kuo YH, Kuo YJ, Yu AS, Wu MD, Ong CW, Kuo LMY, Huang JT, Chen CF and Li SY. (2003). Two novel sesquiterpene lactones, cytotoxic vernolide-A and-B, from Vernonia cinerea. Chemical and Pharmaceutical Bulletin. 51:425-426. https://doi.org/10.1248/cpb.51.425
  17. Lee CS, Jeong EB, Kim YJ, Lee MS, Seo SJ, Park KH and Lee MW. (2013). Quercetin-3-O-($2^{\prime\prime}$-galloyl)-${\alpha}$-L-rhamnopyranoside inhibits TNF-${\alpha}$-activated NF-${\kappa}B$-induced inflammatory mediator production by suppressing ERK activation. International Immunopharmacology. 16:481-487. https://doi.org/10.1016/j.intimp.2013.05.001
  18. Manach C, Mazur A and Scalbert A. (2005). Polyphenols and prevention of cardiovascular diseases. Current Opinion in Lipidology. 16:77-84. https://doi.org/10.1097/00041433-200502000-00013
  19. Masuda T and Jitoe A. (1995). Phenylbutenoid monomers from the rhizomes of Zingiber cassumunar. Phytochemistry. 39:459-461. https://doi.org/10.1016/0031-9422(94)00883-U
  20. Middleton E Jr, Kandaswami C and Theoharis TC. (2000). The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacological Reviews. 52:673-751.
  21. Min BS and Cuong TD. (2013). Phenolic compounds from Caesalpinia sappan and their inhibitory effects on LPS-induced NO production in RAW 264.7 cells. Natural Product Sciences. 19:201-205.
  22. Misra TN, Singh RS, Upadhyay J and Srivastava R. (1984a). Chemical constituents of Vernonia cinerea, part I. Isolation and spectral studies of triterpenes. Journal of Natural Products. 47:368-372. https://doi.org/10.1021/np50032a023
  23. Misra TN, Singh RS, Upadhyay J and Srivastava R. (1984b). Isolation of a natural sterol and an aliphatic acid from Vernonia cinerea. Phytochemistry. 23:415-417. https://doi.org/10.1016/S0031-9422(00)80343-X
  24. Moncada SRMJ, Palmer RML and Higgs EA. (1991). Nitric oxide: Physiology, pathophysiology, and pharmacology. Pharmacological Reviews. 43:109-142.
  25. Park EJ, Kondratyuk TP, Morrell A, Kiselev E, Conda-Sheridan M, Cushman M, Ahn S, Choi Y, White JJ, van Breemen RB and Pezzuto JM. (2011). Induction of retinoid X receptor activity and consequent upregulation of p21WAF1/CIP1 by indenoisoquinolines in MCF7 cells. Cancer Prevention Research. 4:592-607. https://doi.org/10.1158/1940-6207.CAPR-10-0004
  26. Pratheeshkumar P and Kuttan G. (2011). Effect of vernolide-A, a sesquiterpene lactone from Vernonia cinerea L., on cellmediated immune response in B16F-10 metastatic melanomabearing mice. Immunopharmacology and Immunotoxicology. 33:533-538. https://doi.org/10.3109/08923973.2010.547501
  27. Tandon M, Shukla YN, Tripathi AK and Singh SC. (1998). Insect antifeedant principles from Vernonia cinerea. Phytotherapy Research. 12:195-199. https://doi.org/10.1002/(SICI)1099-1573(199805)12:3<195::AID-PTR223>3.0.CO;2-#
  28. Wang C, Yang Y, Mei Z and Yang X. (2013). Cytotoxic compounds from Laminaria japonica. Chemistry of Natural Compounds. 49:699-701. https://doi.org/10.1007/s10600-013-0711-0
  29. Youn UJ, Park EJ, Kondratyuk TP, Simmons CJ, Borris RP, Tanamatayarat P, Wongwiwatthananukit S, Toyama O, Songsak T, Pezzuto JM and Chang LC. (2012). Antiinflammatory sesquiterpene lactones from the flower of Vernonia cinerea. Bioorganic and Medicinal Chemistry Letters. 22:5559-5562. https://doi.org/10.1016/j.bmcl.2012.07.010