Skip to main content
Log in

Flavonoids fromIris spuria (Zeal) cultivated in Egypt

  • Research Article
  • Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

A new 12a-dehydrorotenoid 1, 11-dihydroxy-9, 10-methylenedioxy-12a-dehydrorotenoid(1), together with a new isoflavonoid glycoside tectorigenin-7-O-β-glucosyl-4’-O-β-glucoside(3), were isolated and identified from the rhizomes ofI. spuria (Zeal). In addition, 4 known compounds, tectorigenin(2) tectorigenin-7-O-β-glucosyl (1 → 6) glucoside(4), tectoridin (a tectorigenin-7-O-β-glucoside)(5) and tectorigenin-4’-O-β-glucoside(6) were isolated and identified for the first time from this plant. The structures of the isolated compounds were determined by spectroscopic methods (UV, IR,1H,13C-NMR, DEPT, HMQC, NOESY, and HMBC experiments and MS spectrometry) and by comparison with literature data of known compounds. Compounds2, 4, 5, and6 are reported for the first time from this plant through the present study.

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.

Similar content being viewed by others

References

  • Agrawal, P. K.,Carbon-13 NMR of Flavonoids, Elsevier Sciences Publishing Company INC, New York, p. 5 (1989).

    Google Scholar 

  • Agarwal, V. K., Thappa, R. K., Agarwal, S. G., and Dhar, K. L., Phenolic constituents ofIris milesii rhizomes.Phytochemistry, 23, 1342–1343 (1984).

    Article  CAS  Google Scholar 

  • Breitmaier, Em. and Voelter, W.,Carbon-13 NMR Spectroscopy 3rd ed. VCH Publishers, New York (1987).

    Google Scholar 

  • Dewick, P. M., The Shikimate Pathway, In:Medicinal natural products: a biosynthetic approach, 2nd ed., John Wiley & Sons Ltd, New York, p. 155 (2002).

    Google Scholar 

  • Elangovan, V., Sekar, N., and Govindasamy, S., Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis.Cancer Lett., 87, 107–113 (1994).

    Article  PubMed  CAS  Google Scholar 

  • El-Hadidi, M. N. and Fayed, A. A.,Taeckholmia., Giza 12613, Egypt, Cairo University Herbarium, No. 15, p. 189 (1995).

    Google Scholar 

  • Farag, F. S., Backheet, Y. E., El-Emary, A. N., and Niwa, M., Isoflavonoids and flavone glycosides from rhizomes ofIris carthaliniae.Phytochemistry, 50, 1407–1410 (1999).

    Article  CAS  Google Scholar 

  • Harborne, J. B., Mabry, T. J., and Mabry, H.,The Flavonoids, Academic Press, London, New York (1975).

    Google Scholar 

  • Ito, C., Itoigawa, M., Kojima, N., Tan, H.,Takayasu, J., Tokuda, H., Nishino, H., and Furukawa, H., Cancer chemoprevantive activity of rotenoids fromDenis trifoliata.Planta Med., 70, 8–11 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Kan, W. S., Manual of Medicinal Plants in Taiwan;National Research Institute of Chinese Medicine, Taiwan, 2, 276–280 (1972).

    Google Scholar 

  • Li, L., Wang, H. K., Chang, J. J., McPhail, A. T., McPhail, D., and Terada, H., Anti-tumor agents, 138. Rotenoids and isoflavones as cytotoxic constituents fromAmorpha jruticosa.J. Nat. Prod., 56, 960–968 (1993).

    Google Scholar 

  • Mabry, T. J., Markham, K. R., and Thomas, M. B.,The systematic Identification of Flavonoids. Springer-Verlag, Berlin (1970).

    Google Scholar 

  • Marner, F.-J., Singab, B. A., Al-Azizi, M. M., El-Emary, A. N., and Schäfer, M., Iridal glycosides fromIris spuria (Zeal), cultivated in Egypt.Phytochemistry, 60, 301–307 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Messana, I., Ferrara, F., and Goulart Santana, E. A., Two 12a-hydroxyrotenoids fromBoerhaavia cocciniea.Phytochemistry, 25, 2688–2689 (1986).

    Article  CAS  Google Scholar 

  • Nagarajan, N. S. and Narayanan, V., Chemical constituents of the roots ofDalbergia sissoides.Fitoterapia, 59(4), 341–342 (1988).

    CAS  Google Scholar 

  • Shawl, S. A., Mengi, N., Kaul, K. M., and Vishwapaul, Flavonoids ofIris spuria.Phytochemistry, 27, 1559–1560 (1988a).

    Article  CAS  Google Scholar 

  • Shawl, S. A., Mengi, N., Misra, N. L., and Vishwapaul, Irispurinol, a 12a-hydroxyrotenoid fromIris spuria.Phytochemistry, 27, 3331–3332 (1988b).

    Article  CAS  Google Scholar 

  • Shawl, S. A., Vishwapaul, Asif, Z., and Kalla, K. A., Isoflavones ofIris spuria.Phytochemistry, 23, 2405–2406 (1984).

    Article  CAS  Google Scholar 

  • Shawl, S. A. and Kumar, T., Isoflavonoids fromIris crocea.Phytochemistry, 31, 1399–1401 (1992).

    Article  CAS  Google Scholar 

  • Shin, H. K., Kim, Y. P., Lim, S. S., Lee, S., Ryu, N., Yamada, M., and Ohuchi, K., Inhibition of prostaglandin E2 production by the isoflavones tectorigenin and tectordin isolated from the rhizomes ofBelamcanda chinensis.Plants Med., 65, 776–777 (1999).

    Article  CAS  Google Scholar 

  • Wollenweber, E., Stevens, J. J., Klimo, K., Knauft, J., Frank, N., and Gerhäuser, C., Cancer chemoprevantivein vitro activities of isoflavones isolated fromIris germanica.Planta Med., 69, 15–20 (2003).

    Article  PubMed  CAS  Google Scholar 

  • Yamaki, K., Kim, H. D., Ryu, N., Kim, P. Y., Shin, H. K., and Ohuchi, K., Effects of naturally occurring isoflavones on prostaglandin E2 production.Planta Med., 68, 97–100 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Yamazaki, T., Nakajima, Y., Niho, Y., Hosono, T., Kurashige, T., Kinjo, J., and Nohara, T., Pharmacological studies onPuerariae flos III: protective effects of kakkalide on ethanolinduced lethality and acute hepatic injury in mice.J. Pharmacy & Pharmacology, 49, 831–833 (1997).

    CAS  Google Scholar 

  • Yasukawa, K., Takido, M., Takeuchi, M., and Nakagawa, S., Effect of chemical constituents from plants on 12-O- tetradecanoylphorbol-13-acetate induced inflammation in mice.Chem. Pharm. Bull., 37, 1071–1073 (1989).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Abdel Nasser B. Singab.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singab, A.N.B. Flavonoids fromIris spuria (Zeal) cultivated in Egypt. Arch Pharm Res 27, 1023–1028 (2004). https://doi.org/10.1007/BF02975425

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02975425

Keywords

Navigation