Medicinal Chemistry Research

, Volume 22, Issue 12, pp 5700–5706 | Cite as

Protective effect of Centaurea pallescens Del. against CCl4-induced injury on a human hepatoma cell line (Huh7)

  • Hossam M. Abdallah
  • Mona A. Mohamed
  • Allia M. Abdou
  • Manal M. Hamed
  • Ashraf B. Abdel-Naim
  • Osama M. Ashour
Original Research
First Online:
Received:
Accepted:

Abstract

Through a hepatoprotective bioassay-guided fractionation of the methanol extract from Centaurea pallescens Del. (Asteraceae), a new acylated flavonoid triglycoside, 4′-methoxy kaempferol 3-O-[α-l-rhamnopyranosyl-(1→3)-(2-O-E-p-coumaroyl)] β-d-glucopyranoside-7-O-(4-O-E-p-coumaroyl) α-l-rhamnopyranoside (1) was isolated from the highly active aqueous fraction. In addition, six known compounds were isolated from both aqueous (2–3) and ethyl acetate soluble fractions (4–7). The structure of (1) was determined by comprehensive analysis of 1D and 2D NMR and mass spectral data. The protective effects of the methanol extract of C. pallescens and its fractions on the human hepatoma cell line were evaluated using Silymarin as a positive control. Hepatoprotection was assessed through determination of aspartate aminotransferase (AST), alanine transaminase (ALT), and superoxide dismutase (SOD) activities in addition to glutathione (GSH) levels before and after incubating the cells with carbon tetrachloride. Compound 1, the major constituent of the aqueous fraction, showed a significant cytoprotection at 100 μg/mL as evidenced by decreasing ALT activity to 18.6 ± 0.12, and enhancing SOD activity to 264.6 ± 4.3 U/mL. Meanwhile, compound 2 at 10 μg/mL decreased AST activity to 5.8 ± 2.4 U/mL. Moreover, Compounds 2 and 3 at 1,000 μg/mL significantly enhanced GSH levels. In conclusion, the protective effects of C. pallescens extract, its fractions and compounds 1–3 are concluded to be partly mediated by its antioxidant activity.

Keywords

Centaurea pallescens Acylated methoxy kaempferol Hepatoprotective 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

The authors are indebted and grateful to Prof. Dr. Olov Sterner and Dr. Karl-Erik Bergquist, faculty of science, Lund university, Sweden, for performing spectral data for all the isolated compounds.

Supplementary material

44_2013_563_MOESM1_ESM.docx (398 kb)
Supplementary material 1 (DOCX 397 kb)

References

  1. Abdallah HM, Ezzat SM, El Salah, Dine R, Abdel-Sattar E, Abdel-Naim AB (2013) Protective effect of Echinops galalensis against CCl4-induced injury on the human hepatoma cell line (Huh7). Phytochem Lett 6:73–78CrossRefGoogle Scholar
  2. Achliya GS, Wadodkar SG, Dorle AK (2004) Evaluation of hepatoprotective effect of Amalkadi Ghrita against carbon tetrachloride induced hepatic damage in rats. J Ethnopharmacol 90:229–232CrossRefPubMedGoogle Scholar
  3. Al-easa HS, Mann J, Rizk A (1990) Guaianolides from Centaurea sinaica. Phytochemistry 29:1324–1325CrossRefGoogle Scholar
  4. Amer MMA, Salama OM, Omar AA (1984) Methylated flavonoidal aglycones from Centaurea alexandrina. Acta Pharm Jugosl 34:257Google Scholar
  5. Amresh G, Rao ChV, Singh PN (2007) Antioxidant activity of Cissampelos pareira on benzo (a) pyrene induced mucosal injury in mice. Nutr Res 27:625–632CrossRefGoogle Scholar
  6. Ashok Shenoy K, Somayaji SN, Bairy KL (2001) Hepatoprotective effects of Ginkgo biloba against carbon tetrachloride induced hepatic injury in rats. Indian J Pharmacol 33:260–266Google Scholar
  7. Bishayee A, Sarkar A, Chatterjee M (1995) The hepatoprotective activity of carrot (Daucus carota L) against carbon tetrachloride intoxication in mouse liver. J Ethnopharmacol 47:69–74CrossRefPubMedGoogle Scholar
  8. Bohm BA, Stuessy TF (2001) Flavonoids of the sunflower family (Asteraceae). Springer, WienCrossRefGoogle Scholar
  9. Castro JA, de Ferreyra GC, de Castro CR, Sesame H, de Fenos OM, Gillette JR (1974) Prevention of carbon tetrachloride induced necrosis by inhibitors of drug metabolism. Further studies on the metabolism of their action. Biochem Pharmacol 23:295–302CrossRefPubMedGoogle Scholar
  10. Chatterjee TK (2000) Medicinal plants with hepatoprotective properties in herbal opinions, vol vol III. Books and Allied (P) Ltd., Calcutta, p 135Google Scholar
  11. Chattopadhyay RR (2003) Possible mechanism of hepatoprotective activity of Azadirachta indica leaf extract Part II. J Ethnopharmacol 89:217–219CrossRefPubMedGoogle Scholar
  12. Dianzani MU, Muzia G, Biocca ME, Canuto RA (1991) Lipid peroxidation in fatty liver induced by caffeine in rats. Int J Tissue React 13:79–85PubMedGoogle Scholar
  13. Felice S, Apostolides AN, Maurizio B (2005) Volatile components of Centaurea eryngiodes Lam. and Centaurea iberica Trev. var. hermonis Bois. Lam., two Asteraceae growing wild in Lebanon. Nat Prod Res 19:749–754CrossRefGoogle Scholar
  14. Fernández MA, García MD, Sáenz MT (1996) Antibacterial activity of the phenolic acids fractions of Scrophularia frutescens and Scrophularia sambucifolia. J Ethnopharmacol 53:11–14CrossRefPubMedGoogle Scholar
  15. Harraz FM, Masaouda EA (1988) 1H- and 13C-NMR assignments and cytotoxic activity of the lignan glucoside arctiin from centaurea Alexandrina Del. Alex J Pharm Sci 11:168–171Google Scholar
  16. Hegnauer R (1989) Chemotaxonomie der Pflanzen VIII. Birkhäuser-Verlag, Basel Boston BerlinCrossRefGoogle Scholar
  17. Helal HM, Nakamura N, Meselhy MR, El-Fishawy AM, Hattori M, Mahran GH (1998) Guaianolides from Centaurea scoparia. Phytochemistry 45:551–554CrossRefGoogle Scholar
  18. Ismail SI, Hammouda FM, Rimpler H, Abdallah SM (1986) Methylated flavonoidal aglycones from Centaurea alexandrina. Planta Med 52:527CrossRefGoogle Scholar
  19. Karawya MS, Hilal SH, Hifnawy MS, El-Hawary SS (1975) Phytochemical study of Centaurea calcitrapa L. growing in Egypt. Egypt J Pharm Sci 16:429–444Google Scholar
  20. Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, New YorkCrossRefGoogle Scholar
  21. Markham KR, Chari VM (1982) Carbon-13 NMR spectroscopy of flavonoids. In: Harborne JB, Mabry TJ (eds) The flavonoids: advances in research. Chapman and Hall, LondonGoogle Scholar
  22. Marklund S, Marklund G (1974) Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur J Biochem 47:469–474CrossRefPubMedGoogle Scholar
  23. McRae JM, Yang Q, Crawford RJ, Palombo EA (2008) Acylated flavonoid tetraglycoside from Planchonia careya leaves. Phytochem Lett 1:99–102CrossRefGoogle Scholar
  24. Mohamed MA, Marzouk MSA, Moharram FA, El-Sayed MM, Baiuomy AR (2005) Phytochemical constituents and hepatoprotective activity of Viburnum tinus. Phytochemistry 66:2780–2786CrossRefPubMedGoogle Scholar
  25. Mohamed MA, Ahmed WS, El-Said MM, Hayen H (2008) New acylated flavonol diglycosides of Cynanchum acutum leaves. Nat Prod Commun 2:193–198Google Scholar
  26. Muhammed SM (1989) A pharmacognostical study of certain Centaurea species (Centaurea alexandrina, C. pallescens and C. glomerata family; Compositae). M. Sc. Thesis, Alexandria University, EgyptGoogle Scholar
  27. Ohkawa H, Ohishi N, Yagi K (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 95:351–358CrossRefPubMedGoogle Scholar
  28. Recknagel RO (1983) A new direction in the study of carbon tetrachloride hepatotoxicity. Life Sci 33:401–408CrossRefPubMedGoogle Scholar
  29. Reitman S, Frankel S (1957) A colorimetric method for the determination of serum glutamic oxalacetic and glutamic pyruvic transaminases. Am J Clin Pathol 28:56–63PubMedGoogle Scholar
  30. Subramoniam A, Pushpangadan P (1999) Development of phytomedicine for liver diseases. Indian J Pharmacol 31:166–175Google Scholar
  31. Tackholm V (1974) Student’s flora of Egypt, 2nd edn. Cairo University, Cooperative Printing Company, Beirut, p 413Google Scholar
  32. Thabrew MI, Joice PDTM, Rajatissa WA (1987) Comparative study of efficacy of Paetta indica and Osbeckia octandra in the treatment of liver dysfunction. Planta Med 53:239–241CrossRefPubMedGoogle Scholar
  33. Torres-Gonzalez L, Munoz-Espinosa LE, Rivas-Estilla AM, Trujillo-Murillo K, Salazar-Aranda R, Waksman De Torres N, Cordero-Perez P (2011) Protective effect of four Mexican plants against CCl4-induced damage on the Huh7 human hepatoma cell line. Ann Hepatol 10:73–79PubMedGoogle Scholar
  34. Wendel A, Feurensteins S, Konz KH (1987) Acute paracetamol intoxication of starved mice leads to lipid peroxidation in vivo. Biochem Pharmacol 28:2051–2053CrossRefGoogle Scholar
  35. Youssef DTA (1998) Sesquiterpene lactones of Centaurea scoparia. Phytochemistry 49:1733–1737CrossRefPubMedGoogle Scholar
  36. Youssef AE, Abdallah OA, Sarg TM, David SJ (1987) Chemical constituents of Centaurea pallescens. Planta Med 53:5CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Hossam M. Abdallah
    • 1
    • 2
  • Mona A. Mohamed
    • 3
  • Allia M. Abdou
    • 3
  • Manal M. Hamed
    • 3
  • Ashraf B. Abdel-Naim
    • 4
  • Osama M. Ashour
    • 4
  1. 1.Department of Natural Products, Faculty of PharmacyKing Abdulaziz UniversityJeddahSaudi Arabia
  2. 2.Department of Pharmacognosy, Faculty of PharmacyCairo UniversityCairoEgypt
  3. 3.Department of Medicinal ChemistryTheodor Bilharz Research Institute (TBRI)GizaEgypt
  4. 4.Department of Pharmacology and Toxicology, Faculty of PharmacyKing Abdulaziz UniversityJeddahSaudi Arabia

Personalised recommendations