Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Anti-human immunodeficiency virus-type 1 activity of constituents fromJuglans mandshurica

  • 120 Accesses

  • 31 Citations

Abstract

Three naphthalene glycosides (1-3), four flavonoids (4-7), and two galloyl glycosides (8-9) were isolated from the stem-bark ofJuglans mandshurica (Juglandaceae). Their structures were determined by chemical and spectral means, including to 2D-NMR (COSY, HMQC, and HMBC) experiments. Amongst the isolated compounds, taxifolin (4) showed the most potent HIV-induced cytopethic activity against MT-4 cells with complete inhibitory concentration (IC100) value of 25 μg/ml and maximum cytotoxic concentration (CC100) value of above 100 μg/ml. However, naphthalene glycosides (1-3), flavonoids (5-7)), and galloyl tannins (8-9) were inactive against anti-HIV-1 activity.

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

References

  1. DeClerq E., Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections.J. Med. Chem., 38, 2491–2517 (1995).

  2. El-Mekkawy S., Meselhy M. R., Nakamura N., Hattori M., Kawahata T., Otake T., Anti-HIV-1 phorbol esters from the seeds ofCroton tiglium.Phytochemistry, 53, 457–464 (2000).

  3. Fauci A. S., The human immunodeficiency virus: infectivity and mechanism of pathogenesis.Science, 239, 617–622 (1990).

  4. Goff S. P., Retroviral reverse transcriptase: synthesis, structure, and function.J. AIDS, 3, 617–622 (1988).

  5. Harada, S., Koyanagi, Y. and Yamamoto, N., Infection of HTLV-lll/LAV in HTLV-1-carrying cells MT-2 and MT-4 and application in a plaque assay.Science, 229, 563–566 (1985).

  6. Joe Y. K., Son J. K., New naphthalenyl glucosides from the roots ofJuglans mandshurica.J. Nat. Prod., 59, 159–160 (1996).

  7. Kawahata T., Otake T., Mori H., Morimoto M., Ueba N., Kusumoto I. T., El-Mekkawy S., Hattori M., Namba T., Screening of Egyptian folk medicinal plant extracts for anti-human immunodeficiency virus type-1 (HIV-1) activity.J. Traditional Med., 13, 59–65 (1996).

  8. Kim S. H., Lee K. S., Son J. K., Je G. H., Lee J. S., Lee C. H., Cheong C. J., Cytotoxic compounds from the roots ofJuglans mandshurica.J. Nat. Prod., 61, 643–645 (1998).

  9. Kusumoto I. T., Nakabayashi T., Kida H., Miyashiro H., Hattori M., Namba T., Screening of various plant extracts used in Ayurvedic medicine for inhibitory effects on human immunodeficiency virus type I (HIV-1) protease.Phytother. Res., 9, 180–184 (1995).

  10. Lee S. W., Lee K. S., Son J. K., New naphthalenyl glycosides from the roots ofJuglans mandshurica.Planta Med., 66, 184–186 (2000).

  11. Lim Y. S., Kojima S., Nakamura N., Miyashiro H., Fushimi H., Komatsu K., Hattori M., Shimotohno K., Gupta M. P., Correa M., Inhibitory effects ofCordia spinescens extracts and their constituents on reverse transcriptase and protease from human immunodeficiency virus.Phytother. Res., 11, 490–495 (1997a).

  12. Lim Y. S., Ma C. M., Kusumoto I. T., Miyashiro H., Hattori M., Gupta M. P., Correa M., HIV-1 reverse transcriptase inhibitory principles fromChamaesyce hyssopifolia.Phytother. Res., 11, 22–27 (1997b).

  13. Loya S., Hizi A., The interaction of illimaquinone, a selective inhibitor of the RNase H activity, with the reverse transcriptases of human.J. Biol. Chem., 268, 9323–9328 (1993).

  14. Matsuse I. T., Nakabayashi T., Lim Matsuse I. T., Nakabayashi T., Lim Y. A., Ghazi M. E. H., Miyashiro H., Kakiuchi N., Hattori M., Stardjo S., Shimotohno K., A human immunodeficiency virus protease inhibitory substance fromSwiertenia mahagoni.Phytother. Res., 11, 433–436 (1997).

  15. Min, B. S., Nakamura N., Miyashiro H., Kim Y. H., Hattori M., Inhibition of human immunodeficiency virus type I reverse transcriptase and ribonuclease H activities by constituents ofJuglans mandshurica.Chem. Pharm. Bull., 48, 194–200 (2000).

  16. Moriya T., Saito K., Kurita H., Matsumoto K., Otake T., Mori H., Morimoto M., Ueba N., Kunita N.,J. Med. Chem., 36, 1674–1677 (1993).

  17. Son J. K., Isolation and structure determination of a new tetralone glucoside from the roots ofJuglans mandshurica.Arch. Pharm. Res., 18, 203–205 (1995).

Download references

Author information

Correspondence to Byung Sun Min or Hyeong Kyu Lee or Sang Myung Lee or Young Ho Kim or Ki Hwan Bae or Toru Otake or Norio Nakamura or Masao Hattori.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Min, B.S., Lee, H.K., Lee, S.M. et al. Anti-human immunodeficiency virus-type 1 activity of constituents fromJuglans mandshurica . Arch Pharm Res 25, 441–445 (2002). https://doi.org/10.1007/BF02976598

Download citation

Key words

  • Juglans mandshurica
  • Taxifolin
  • Anti-HIV activity
  • MT-4 cells