Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Anti-Human Immunodeficiency Virus-Type 1 Activity of Constituents from Juglans mandshurica

  • Min, Byung-Sun (Immunomodulator Research Laboratory, KRIBB) ;
  • Lee, Hyeong-Kyu (Immunomodulator Research Laboratory, KRIBB) ;
  • Lee, Sang-Myung (Immunomodulator Research Laboratory, KRIBB) ;
  • Kim, Young-Ho (College of Pharmacy, Chungnam National University) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University) ;
  • Otake, Toru (Osaka Prefectural Institute of Public health, Osaka, Japan) ;
  • Nakamura, Norio (Institute of Natural Medicine, Toyama Medical ＆ Pharmaceutical University) ;
  • Hattori, Masao (Institute of Natural Medicine, Toyama Medical ＆ Pharmaceutical University)
  • Published : 2002.08.01
Download PDF
⟨ Previous Next ⟩

Abstract

Three naphthalene glycosides (1-3), four flavonoids (4-7), and two galloyl glycosides (8-9) were isolated from the stem-bark of Juglans 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 ($IC_{100}$) value of $25{\;}{\mu\textrm{g}}/ml$ and maximum cytotoxic concentration ($CC_{100}$) value of above $100{\;}{\mu\textrm{g}}/ml$. However, naphthalene glycosides (1-3), flavonoids (5-7)), and galloyl tannins (8-9) were inactive against anti-HIV-1 activity.

Keywords

References

  1. DeClerq E., Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem., 38, 2491-2517 (1995) https://doi.org/10.1021/jm00014a001
  2. EI-Mekkawy S., Meselhy M. R., Nakamura N., Hattori M., Kawahata T., Otake T., Anti-HIV-1 phorbol esters from the seeds of Croton tiglium. Phytochemistry, 53, 457-464 (2000) https://doi.org/10.1016/S0031-9422(99)00556-7
  3. Fauci A. S., The human immunodeficiency virus: infectivity and mechanism of pathogenesis. Science, 239, 617-622 (1990) https://doi.org/10.1126/science.3277274
  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-Ill/LAV in HTLV-1-carrying cells MT-2 and MT-4 and application in a plaque assay. Science, 229, 563-566 (1985) https://doi.org/10.1126/science.2992081
  6. Joe Y. K., Son J. K., New naphthalenyl glucosides from the roots of Juglans mandshurica. J. Nat. Prod., 59, 159-160 (1996) https://doi.org/10.1021/np9600356
  7. Kawahata T., Otake T., Mori H., Morimoto M., Ueba N., Kusumoto I. T., EI-Mekkawy S., Hattori M., Namba T.,Screening of Egyptian folk medicinal plant extracts for antihuman 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 of Juglans mandshurica. J. Nat. Prod., 61, 643-645 (1998) https://doi.org/10.1021/np970413m
  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) https://doi.org/10.1002/ptr.2650090305
  10. Lee S. W., Lee K. S., Son J. K., New naphthalenyl glycosides from the roots of Juglans mandshurica. Planta Med., 66, 184-186 (2000) https://doi.org/10.1055/s-0029-1243129
  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 of Cordia spinescens extracts and their constituents on reverse transcriptase and protease from human immunodeficiency virus. Phytother. Res., 11, 490-495(1997a) https://doi.org/10.1002/(SICI)1099-1573(199711)11:7<490::AID-PTR134>3.0.CO;2-Y
  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 from Chamaesyce hyssopifolia. Phytother. Res., 11, 22-27 (1997b) https://doi.org/10.1002/(SICI)1099-1573(199702)11:1<22::AID-PTR951>3.0.CO;2-3
  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 from Swiertenia mahagoni. Phytother. Res., 11, 433-436 (1997) https://doi.org/10.1002/(SICI)1099-1573(199709)11:6<433::AID-PTR122>3.0.CO;2-#
  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 of Juglans mandshurica. Chem. Pharm. Bull., 48, 194-200 (2000) https://doi.org/10.1248/cpb.48.194
  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) https://doi.org/10.1021/jm00063a018
  17. Son J. K., Isolation and structure determination of a new tetralone glucoside from the roots of Juglans mandshurica. Arch. Pharm. Res., 18, 203-205 (1995) https://doi.org/10.1007/BF02979196