Skip to main content

Advertisement

Log in

Free radical scavengers from the aerial parts of Euphorbia petiolata

  • Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. Mozaffarian V (1996) A dictionary of Iranian plant names. Farhang Mo’aser, Tehran, p 219

    Google Scholar 

  2. Rechinger KH, Schiman-Czeika H (1963) Euphorbiaceae. In: Rechinger KH (ed) Flora Iranica, no. 6. Akademische Druck-und Verlagsanstalt, Graz

    Google Scholar 

  3. Pahlevani AH (2007) Notes on some species of the genus Euphorbia in Iran. Rostaniha 8:89–103

    Google Scholar 

  4. Mir Heydar H (2006) Maaref Ghiahi, vol 4. Daftar-e Nashr, Tehran, pp 285–293

    Google Scholar 

  5. Singla AK, Pathak K (1990) Phytoconstituents of Euphorbia species. Fitoterapia 6:483–516

    Google Scholar 

  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 109:134–139

    Article  CAS  PubMed  Google Scholar 

  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 110:294–304

    Article  PubMed  Google Scholar 

  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. Jassbi AR (2006) Chemistry and biological activity of secondary metabolites in Euphorbia from Iran. Phytochemistry 67:1977–1984

    Article  CAS  PubMed  Google Scholar 

  10. Shi YP, Ma B, Jia ZJ, Lahham J, Saleh SA (1996) A new ingenol ester from Euphorbia petiolata. Chin Chem Lett 7:439–440

    CAS  Google Scholar 

  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 36:1038–1043

    Google Scholar 

  12. Shi YP, Jia ZJ, Ma B, Saleh SA, Lahham J (1996) Ingenane diterpenes from Euphorbia petiolata. Planta Med 62:260–262

    Article  CAS  PubMed  Google Scholar 

  13. Rustaiyan A, Niknejad A, Sharif Z, Izaddoost M (1982) Triterpenes from Euphorbia petiolata. Fitoterapia 53:143–144

    CAS  Google Scholar 

  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 62:91–95

    Article  CAS  PubMed  Google Scholar 

  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 2:89–91

    CAS  Google Scholar 

  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 44:174–177

    Article  Google Scholar 

  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 43:736–737

    Article  CAS  Google Scholar 

  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 67:2176–2181

    Article  CAS  PubMed  Google Scholar 

  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 33:87–90

    Article  CAS  Google Scholar 

  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) 16:286–290

    CAS  Google Scholar 

  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 40:24–27

    Article  CAS  Google Scholar 

  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 14:109–114

    CAS  Google Scholar 

  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 12:49–53

    CAS  Google Scholar 

  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 3:222–227

    Google Scholar 

  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 43:112–114

    Article  CAS  Google Scholar 

  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 20:167–172

    Article  CAS  PubMed  Google Scholar 

  27. Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, New York

    Google Scholar 

  28. Agrawal PK (1989) Carbon-13 NMR of flavonoids. Elsevier, Amsterdam

    Google Scholar 

  29. Markham KR (1982) Techniques of flavonoid identification. Academic, London

    Google Scholar 

  30. Harborne JB, Mabry TJ (1982) The flavonoids: advances in research. Chapman and Hall, London

    Google Scholar 

  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. 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 31:2719–2726

    Article  CAS  Google Scholar 

  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 18:463–470

    CAS  Google Scholar 

  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 53:757–761

    Article  CAS  PubMed  Google Scholar 

  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 30:451–459

    Article  CAS  PubMed  Google Scholar 

  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 58:1780–1783

    Article  CAS  Google Scholar 

  37. Kumarasamy Y, Fergusson M, Nahar L, Sarker SD (2002) Biological activity of moschamindole from Centaurea moschata. Pharm Biol 40:307–310

    Article  CAS  Google Scholar 

  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 40:122–128

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Satyajit Dey Sarker.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nazemiyeh, H., Kazemi, E.M., Zare, K. et al. Free radical scavengers from the aerial parts of Euphorbia petiolata . J Nat Med 64, 187–190 (2010). https://doi.org/10.1007/s11418-009-0382-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-009-0382-0

Keywords

Navigation