Advertisement

Journal of Natural Medicines

, Volume 64, Issue 2, pp 187–190 | Cite as

Free radical scavengers from the aerial parts of Euphorbia petiolata

  • Hossein Nazemiyeh
  • Elham Mohajjel Kazemi
  • Khadijeh Zare
  • Malakeh Jodari
  • Lutfun Nahar
  • Satyajit Dey Sarker
Note

Abstract

Reversed-phase preparative high-performance liquid chromatography (HPLC) of the methanol extract of the aerial parts of Euphorbia petiolata Banks & Soland, an endemic Iranian medicinal plant, yielded ten free radical scavengers including eight flavonoid glycosides myricetin 3-O-glucoside (1), kaempferol 3-O-(2-O-galloyl)-glucoside (2), myricetin 3-O-rhamnoside (3), quercetin 3-O-glucoside (4), kaempferol 3-O-glucoside (5), quercetin 3-O-rhamnoside (6), kaempferol 3-O-rhamnoside (7), and quercetin 3-O-rutinoside (10), a coumarin esculetin (8) and a phenylpropanoid 2-hydroxydihydrocinnamic acid (9). The structures of these compounds were elucidated conclusively by spectroscopic means and also by direct comparison of their spectroscopic data with respective published data. The free radical scavenging properties of these compounds were assessed by the 2,2-diphenyl-1-picrylhydrazyl assay.

Keywords

Euphorbia petiolata Euphorbiaceae Phenolic Flavonoid Antioxidant DPPH 

Notes

Acknowledgments

We thank the Talent Students’ Department, University of Tabriz, for financial support.

References

  1. 1.
    Mozaffarian V (1996) A dictionary of Iranian plant names. Farhang Mo’aser, Tehran, p 219Google Scholar
  2. 2.
    Rechinger KH, Schiman-Czeika H (1963) Euphorbiaceae. In: Rechinger KH (ed) Flora Iranica, no. 6. Akademische Druck-und Verlagsanstalt, GrazGoogle Scholar
  3. 3.
    Pahlevani AH (2007) Notes on some species of the genus Euphorbia in Iran. Rostaniha 8:89–103Google Scholar
  4. 4.
    Mir Heydar H (2006) Maaref Ghiahi, vol 4. Daftar-e Nashr, Tehran, pp 285–293Google Scholar
  5. 5.
    Singla AK, Pathak K (1990) Phytoconstituents of Euphorbia species. Fitoterapia 6:483–516Google Scholar
  6. 6.
    Chaabi M, Freund-Michel V, Frossard N, Randriantsoa A, Andriantsitohaina R, Lobstein A (2007) Anti-proliferative effect of Euphorbia stenoclada in human airway smooth muscle cells in culture. J Ethnopharmacol 109:134–139CrossRefPubMedGoogle Scholar
  7. 7.
    Aburjai T, Hudaib M, Tayyema R, Yousef M, Qishawi M (2007) Ethnopharmacological survey of medicinal herbs in Jordan, the Ajloun Heights region. J Ethnopharmacol 110:294–304CrossRefPubMedGoogle Scholar
  8. 8.
    ISI Web of Science Database (2009) ISI Web of Knowledge. Thomson Reuters, London. http://www.wos.mimas.ac.uk/. Accessed 13 July 2009
  9. 9.
    Jassbi AR (2006) Chemistry and biological activity of secondary metabolites in Euphorbia from Iran. Phytochemistry 67:1977–1984CrossRefPubMedGoogle Scholar
  10. 10.
    Shi YP, Ma B, Jia ZJ, Lahham J, Saleh SA (1996) A new ingenol ester from Euphorbia petiolata. Chin Chem Lett 7:439–440Google Scholar
  11. 11.
    Shi YP, Jia ZJ (1997) Triterpenoids and other constituents from Euphorbia esula and E. petiolata. Indian J Chem Sect B Org Chem Med Chem 36:1038–1043Google Scholar
  12. 12.
    Shi YP, Jia ZJ, Ma B, Saleh SA, Lahham J (1996) Ingenane diterpenes from Euphorbia petiolata. Planta Med 62:260–262CrossRefPubMedGoogle Scholar
  13. 13.
    Rustaiyan A, Niknejad A, Sharif Z, Izaddoost M (1982) Triterpenes from Euphorbia petiolata. Fitoterapia 53:143–144Google Scholar
  14. 14.
    Nazemiyeh H, Rahman MM, Gibbons S, Nahar L, Delazar A, Ghahramani M-A, Talebpour A-H, Sarker SD (2008) Assessment of the antibacterial activity of phenylethanoid glycosides from Phlomis lanceolata against multiple-drug-resistant (MDR) strains of Staphylococcus aureus. J Nat Med 62:91–95CrossRefPubMedGoogle Scholar
  15. 15.
    Nazemiyeh H, Razavi SM, Delazar A, Hajiboland R, Mozaffarian V, Nahar L, Sarker SD (2007) Essential oil composition of the umbels and fruits of Prangos uloptera DC. Nat Prod Commun 2:89–91Google Scholar
  16. 16.
    Nazemiyeh H, Bahadori F, Delazar A, Ay M, Topcu G, Kolak U, Nahar L, Auzi AA, Sarker SD (2007) Tricetin 4′-O-α-l-rhamnopyranoside: a new flavonoid from the aerial parts of Erica arborea. Chem Nat Compd 44:174–177CrossRefGoogle Scholar
  17. 17.
    Nazemiyeh H, Razavi SM, Hajiboland R, Delazar A, Esna-ashari S, Bamdadm R, Nahar L, Sarker SD (2007) Composition of the essential oils of Prangos scabra fruits and inflorescence from Iran. Chem Nat Compd 43:736–737CrossRefGoogle Scholar
  18. 18.
    Delazar A, Biglari F, Nazemiyeh H, Talebpour A, Imani Y, Nahar L, Sarker SD (2006) GC–MS analysis of the essential oils, and the isolation of phenylpropanoid derivatives from the aerial parts of Pimpinella aurea. Phytochemistry 67:2176–2181CrossRefPubMedGoogle Scholar
  19. 19.
    Delazar A, Gibbons S, Kumarasamy Y, Nahar L, Shoeb M, Sarker SD (2005) Antioxidant phenylethanoid glycosides from the rhizomes of Eremostachys glabra (Lamiaceae). Biochem Syst Ecol 33:87–90CrossRefGoogle Scholar
  20. 20.
    Delazar A, Talicgi B, Nazemiyeh Z, Rezazadeh H, Nahar L, Sarker SD (2006) Chrozophorin: a new acylated flavone glucoside from Chrozophora tinctoria. Rev Bras Farmacogn (Braz J Pharmacogn) 16:286–290Google Scholar
  21. 21.
    Delazar A, Reid RG, Sarker SD (2004) GC–MS analysis of essential oil of the oleoresin from Pistacia atlantica var mutica. Chem Nat Compd 40:24–27CrossRefGoogle Scholar
  22. 22.
    Delazar A, Gibbons S, Kosari AR, Nazemiyeh H, Modarresi M, Nahar L, Sarker SD (2006) Flavonoid C-glycosides and cucurbitacin glycosides from Citrullus colocynthis. DARU 14:109–114Google Scholar
  23. 23.
    Delazar A, Shoeb M, Kumarasamy Y, Byres M, Nahar L, Modarresi M, Sarker SD (2004) Two bioactive ferulic acid derivatives from Eremostachys glabra. DARU 12:49–53Google Scholar
  24. 24.
    Fathiazad F, Delazar A, Amiri R, Sarker SD (2006) Extraction of flavonoids and quantification of rutin from waste tobacco leaves. Iran J Pharm Res 3:222–227Google Scholar
  25. 25.
    Delazar A, Naseri M, Nahar L, Moghadam SB, Esnaashari S, Nazemiyeh H, Sarker SD (2007) GC–MS analysis and antioxidant activities of essential oils of two cultivated Artemisia species. Chem Nat Compd 43:112–114CrossRefGoogle Scholar
  26. 26.
    Delazar A, Modarresi M, Shoeb M, Nahar L, Reid RG, Majinda RRT, Sarker SD (2006) Eremostachiin: a new furanolabdane diterpene glycoside from Eromostachys glabra. Nat Prod Res 20:167–172CrossRefPubMedGoogle Scholar
  27. 27.
    Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, New YorkGoogle Scholar
  28. 28.
    Agrawal PK (1989) Carbon-13 NMR of flavonoids. Elsevier, AmsterdamGoogle Scholar
  29. 29.
    Markham KR (1982) Techniques of flavonoid identification. Academic, LondonGoogle Scholar
  30. 30.
    Harborne JB, Mabry TJ (1982) The flavonoids: advances in research. Chapman and Hall, LondonGoogle Scholar
  31. 31.
    SDBS Database (2009) Spectral Database for Organic Compounds (SDBS). National Institute of Advanced Industrial Science and Technology (AIST), Japan. http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng. Accessed 13 July 2009
  32. 32.
    Cussans NJ, Huckerby TN (1975) Carbon-13 NMR spectroscopy of heterocyclic compounds. IV. A 20 MHz study of chemical shifts and carbon-proton coupling constants in a series of hydroxy, methoxy and glucosyl coumarins. Tetrahedron 31:2719–2726CrossRefGoogle Scholar
  33. 33.
    Chung JH, Shin HC, Cho JY, Kang SK, Lee HJ, Shin SC, Park KH, Moon JH (2009) Isolation and structural determination of free radical scavenging compounds from Korean fermented red pepper paste (Kochujang). Food Sci Biotechnol 18:463–470Google Scholar
  34. 34.
    Cimanga K, Ying L, De Bruyne T, Apers S, Cos P, Hermans N, Bakana P, Tona L, Kambu K, Kalenda DT, Pieters L, Vanden Berghe D, Vlietinck AJ (2001) Radical scavenging and xanthine oxidase inhibitory activity of phenolic compounds from Bridelia ferruginea stem bark. J Pharm Pharmacol 53:757–761CrossRefPubMedGoogle Scholar
  35. 35.
    Calvo TR, Lima ZP, Silva JS, Ballesteros KVR, Pellizzon CH, Hiruma-Lima CA, Tamashiro J, Souza Brito ARM, Takahira RK, Vilegas W (2007) Constituents and antiulcer effect of Alchornea glandulosa: activation of cell proliferation in gastric mucosa during the healing process. Biol Pharm Bull 30:451–459CrossRefPubMedGoogle Scholar
  36. 36.
    Takao T, Watanabe N, Yagi I, Sakata K (1994) A simple screening method for antioxidants and isolation of several antioxidants produced by marine-bacteria from fish and shellfish. Biosci Biotechnol Biochem 58:1780–1783CrossRefGoogle Scholar
  37. 37.
    Kumarasamy Y, Fergusson M, Nahar L, Sarker SD (2002) Biological activity of moschamindole from Centaurea moschata. Pharm Biol 40:307–310CrossRefGoogle Scholar
  38. 38.
    Kumarasamy Y, Byres M, Cox PJ, Delazar A, Jaspars M, Nahar L, Shoeb M, Sarker SD (2004) Isolation, structure elucidation and biological activity of flavone C-glycosides from the seeds of Alliaria petiolata. Chem Nat Compd 40:122–128CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer 2009

Authors and Affiliations

  • Hossein Nazemiyeh
    • 1
  • Elham Mohajjel Kazemi
    • 2
  • Khadijeh Zare
    • 2
  • Malakeh Jodari
    • 1
  • Lutfun Nahar
    • 3
  • Satyajit Dey Sarker
    • 4
  1. 1.Research Center for Pharmaceutical Nanotechnology, Faculty of PharmacyTabriz University of Medical SciencesTabrizIran
  2. 2.Talent Students’ CenterUniversity of TabrizTabrizIran
  3. 3.Drug Discovery and Design Research Division, Department of Pharmacy, School of Applied SciencesUniversity of WolverhamptonWolverhamptonUK
  4. 4.Department of Pharmacy, School of Applied SciencesUniversity of WolverhamptonWolverhamptonUK

Personalised recommendations