Skip to main content

Four flavonoids from Echinosophora koreensis and their effects on alcohol metabolizing enzymes

Abstract

A new prenylated dihydroflavonol, 3-hydroxy-kenusanone B 1, as well as three other known isoflavanones, sophoronol 2, sophoraisoflavanone A 3 and kenusanone H 4, were isolated from the rhizomes of Echinosophora koreensis. The structures of these compounds were elucidated using spectroscopic analyses that included extensive 2D NMR, optical rotation spectrometry and mass spectrometry. All four flavonoids enhanced the activities of alcohol metabolizing enzymes such as alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) at micromolar concentrations. Sophoronol 2 showed a nine-fold increased activation of alcohol dehydrogenase and aldehyde dehydrogenase than a negative control group at concentrations of 100 μg/mL and 50 μg/mL, respectively. This study suggests that prenylated flavonoids have the potential to prevent ‘hangovers’ after alcohol intake.

This is a preview of subscription content, access via your institution.

References

  1. Bode, C., Goebell, H., and Stahler, M., Changes in alcohol dehydrogenase activity in rat liver following protein deficiency and ethanol. Z. Ges. Exp. Med., 152, 111–124 (1970).

    Article  CAS  Google Scholar 

  2. Bostian, K. A. and Betts, G. F., Kinetics and reaction mechanism of potassium-activated aldehyde dehydrogenase from Saccharomyces cerevisiae. Biochem. J., 173, 787–798 (1978).

    PubMed  CAS  Google Scholar 

  3. Iinuma, M., Ohyama, M., Tanaka, T., Mizuno, M., and Hong, S. K., An isoflavanone from roots of Echinosophora koreensis. Phytochemistry, 30, 3153–3154 (1991).

    Article  CAS  Google Scholar 

  4. Iinuma, M., Ohyama, M., Tanaka, T., Mizuno, M., and Hong, S. K., Three 2′,4′,6′-trioxygenated flavanones in roots of Echinosophora koreensis. Phytochemistry, 31, 665–669 (1992a).

    Article  CAS  Google Scholar 

  5. Iinuma, M., Ohyama, M., Tanaka, T., Mizuno, M., and Hong, S. K., Three 2′,4′,6′-trioxygenated flavanones in roots of Echinosophora koreensis. Phytochemistry, 31, 2855–2858 (1992b).

    Article  CAS  Google Scholar 

  6. Iinuma, M., Ohyama, M., Tanaka, T., Mizuno, M., and Hong, S.K., Five flavonoid compounds from Echinosophora koreensis. Phytochemistry, 33, 1241–1245 (1993).

    Article  CAS  Google Scholar 

  7. Kim, C. M., Ebizuka, Y., and Sankawa, U., Two new isoflavonoids from Echinosophora koreensis Nakai and the structure revision of sophoronol. Chem. Pharm. Bull., 37, 2879–2881 (1989).

    CAS  Google Scholar 

  8. Komatsu, M., Yokoe, I., and Shirataki, Y., Studies on the constituents of Sophora species XIII. Constituents of the aerial parts of Sophora tomentosa L. Chem. Pharm. Bull., 26, 3863–3870 (1978).

    PubMed  CAS  Google Scholar 

  9. Lee, W. K., Tokuoka, T., and Heo, K., Molecular evidence for the inclusion of the Korean endemic genus “Echinosophora” in Sophora (Fabaceae), and embryological features the genus. J. Plant Res., 117, 209–219 (2004).

    PubMed  Article  CAS  Google Scholar 

  10. McGregor, N. R., Pueraria lobata (Kudzu root) hangover remedies and acetaldehyde-associated neoplasm risk. Alcohol, 41, 469–478 (2007).

    PubMed  Article  Google Scholar 

  11. Murakoshi, I., Fukuchi, K., Haginiwa, J., Ohmiya, S., and Otomasu, H., N-(3-oxobutyl)cytisine: a new lupine alkaloid from Echinosophora koreensis. Phytochemistry, 16, 1460–1461 (1977).

    Article  CAS  Google Scholar 

  12. Murakoshi, I., Watanabe, M., Haginiwa, J., Ohmiya, S., and Otomasu, H., (−)-N-Ethylcytisine, a lupin alkaloid from the flowers of Echinosophora koreensis. Phytochemistry, 21, 1470–1471 (1982a).

    Article  CAS  Google Scholar 

  13. Murakoshi, I., Kidoguchi, E., Kubota, M., Haginiwa, J., Ohmiya, S., and Otomasu, H., Lupine alkaloids from Echinosophora koreensis. Phytochemistry, 21, 2385–2388 (1982b).

    Article  CAS  Google Scholar 

  14. Murakoshi, I., Watanabe, M., Okuda, T., Kidoguchi, E., Haginiwa, J., Ohmiya, S., and Otomasu, H., Lupine alkaloids from flowers of Echinosophora koreensis. Phytochemistry, 24, 2707–2708 (1985).

    Article  CAS  Google Scholar 

  15. Sohn, H. Y., Son, K. H., Kwon, C. S., Kwon, G. S., and Kang, S. S., Antimicrobial and cytotoxic activity of 18 prenylated isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine, 11, 666–672 (2004).

    PubMed  Article  CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Hyun Ok Yang.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Choi, E.J., Kwon, H.C., Sohn, Y.C. et al. Four flavonoids from Echinosophora koreensis and their effects on alcohol metabolizing enzymes. Arch. Pharm. Res. 32, 851–855 (2009). https://doi.org/10.1007/s12272-009-1606-2

Download citation

Key words

  • Echinosophora koreensis
  • Flavonoids
  • 3-Hydroxy-kenusanone B
  • Alcohol dehydrogenase (ADH)
  • Aldehyde dehydrogenase (ALDH)