1887

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Volume 87, Issue 7

1′-1′-Acetoxychavicol acetate isolated from inhibits human immunodeficiency virus type 1 replication by blocking Rev transport Free

Abstract

AIDS remains a major global health concern. Despite a number of therapeutic advancements, there is still an urgent need to develop a new class of therapy for human immunodeficiency virus (HIV). Here, it was shown that 1′-1′-acetoxychavicol acetate (ACA), a small molecular compound isolated from the rhizomes of , inhibited Rev transport at a low concentration by binding to chromosomal region maintenance 1 and accumulating full-length HIV-1 RNA in the nucleus, resulting in a block in HIV-1 replication in peripheral blood mononuclear cells. Additionally, ACA and didanosine acted synergistically to inhibit HIV-1 replication. Thus, ACA may represent a novel treatment for HIV-1 infection, especially in combination with other anti-HIV drugs.

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2006-07-01
2024-04-16
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References

  1. Ando S., Matsuda H., Morikawa T., Yoshikawa M. 2005; 1′ S -1′-Acetoxychavicol acetate as a new type inhibitor of interferon- β production in lipopolysaccharide-activated mouse peritoneal macrophages. Bioorg Med Chem 13:3289–3294 [CrossRef]
     [Google Scholar]
  2. Bevec D., Dobrovnik M., Hauber J., Böhnlein E. 1992; Inhibition of human immunodeficiency virus type 1 replication in human T cells by retroviral-mediated gene transfer of a dominant-negative Rev trans-activator. Proc Natl Acad Sci U S A 89:9870–9874 [CrossRef]
     [Google Scholar]
  3. Bevec D., Jaksche H., Oft M. & 9 other authors 1996; Inhibition of HIV-1 replication in lymphocytes by mutants of the Rev cofactor eIF-5A. Science 271:1858–1860 [CrossRef]
     [Google Scholar]
  4. Biesert L., Zimmermann F., Schroder B., Matthes E., Suhartono H., Dietrich U., Rubsamen-Waigmann H. 1991; Biochemical and genetical analysis of AZT-resistant HIV-mutants. Behring Inst Mitt 89:74–80
     [Google Scholar]
  5. De Pooter H. L., Omar M. N., Coolsaet B. A., Schamp N. M. 1985; The essential oil of greater galanga ( Alpinia galanga ) from Malaysia. Phytochemistry 24:93–96 [CrossRef]
     [Google Scholar]
  6. Duan L., Bagasra O., Laughlin M. A., Oakes J. W., Pomerantz R. J. 1994; Potent inhibition of human immunodeficiency virus type 1 replication by an intracellular anti-Rev single-chain antibody. Proc Natl Acad Sci U S A 91:5075–5079 [CrossRef]
     [Google Scholar]
  7. Felber B. K., Hadzopoulou-Cladaras M., Cladaras C., Copeland T., Pavlakis G. N. 1989; rev protein of human immunodeficiency virus type 1 affects the stability and transport of the viral mRNA. Proc Natl Acad Sci U S A 86:1495–1499 [CrossRef]
     [Google Scholar]
  8. Hadzopoulou-Cladaras M., Felber B. K., Cladaras C., Athanassopoulos A., Tse A., Pavlakis G. N. 1989; The rev ( trs / art ) protein of human immunodeficiency virus type 1 affects viral mRNA and protein expression via a cis -acting sequence in the env region. J Virol 63:1265–1274
     [Google Scholar]
  9. Janssen A. M., Scheffer J. J. C. 1985; Acetoxyhydroxychavicol acetate, an antifungal component of Alpinia galanga . Planta Med 6:507–511
     [Google Scholar]
  10. Kalland K.-H., Szilvay A. M., Brokstad K. A., Sætrevik W., Haukenes G. 1994; The human immunodeficiency virus type 1 Rev protein shuttles between the cytoplasm and nuclear compartments. Mol Cell Biol 14:7436–7444
     [Google Scholar]
  11. Kawabata K., Tanaka T., Yamamoto T. & 7 other authors 2000; Suppression of N -nitrosomethylbenzylamine-induced rat esophageal tumorigenesis by dietary feeding of 1′-acetoxychavicol acetate. Jpn J Cancer Res 91:148–155 [CrossRef]
     [Google Scholar]
  12. Kobayashi Y., Nakae D., Akai H. & 9 other authors 1998; Prevention by 1′-acetoxychavicol acetate of the induction but not growth of putative preneoplastic, glutathione S -transferase placental form-positive, focal lesions in the livers of rats fed a choline-deficient, l-amino acid-defined diet. Carcinogenesis 19:1809–1814 [CrossRef]
     [Google Scholar]
  13. Kudo N., Wolff B., Sekimoto T., Schreiner E. P., Yoneda Y., Yanagida M., Horinouchi S., Yoshida M. 1998; Leptomycin B inhibition of signal-mediated nuclear export by direct binding to CRM1. Exp Cell Res 242:540–547 [CrossRef]
     [Google Scholar]
  14. Kudo N., Matsumori N., Taoka H., Fujiwara D., Schreiner E. P., Wolff B., Yoshida M., Horinouchi S. 1999; Leptomycin B inactivates CRM1/exportin 1 by covalent modification at a cysteine residue in the central conserved region. Proc Natl Acad Sci U S A 96:9112–9117 [CrossRef]
     [Google Scholar]
  15. Lee T. C., Sullenger B. A., Gallardo H. F., Ungers G. E., Gilboa E. 1992; Overexpression of RRE-derived sequences inhibits HIV-1 replication in CEM cells. New Biol 4:66–74
     [Google Scholar]
  16. Malim M. H., Hauber J., Le S.-Y., Maizel J. V., Cullen B. R. 1989; The HIV-1 rev trans -activator acts through a structured target sequence to activate nuclear export of unspliced viral mRNA. Nature 338:254–257 [CrossRef]
     [Google Scholar]
  17. Matsuda H., Morikawa T., Managi H., Yoshikawa M. 2003; Antiallergic principles from Alpinia galanga : structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF- α and IL-4 in RBL-2H3 cells. Bioorg Med Chem Lett 13:3197–3202 [CrossRef]
     [Google Scholar]
  18. Matsukura M., Zon G., Shinozuka K. & 7 other authors 1989; Regulation of viral expression of human immunodeficiency virus in vitro by an antisense phosphorothioate oligodeoxynucleotide against rev ( art / trs ) in chronically infected cells. Proc Natl Acad Sci U S A 86:4244–4248 [CrossRef]
     [Google Scholar]
  19. Menéndez-Arias L. 2002; Targeting HIV: antiretroviral therapy and development of drug resistance. Trends Pharmacol Sci 23:381–388 [CrossRef]
     [Google Scholar]
  20. Meyer B. E., Malim M. H. 1994; The HIV-1 Rev trans-activator shuttles between the nucleus and the cytoplasm. Genes Dev 8:1538–1547 [CrossRef]
     [Google Scholar]
  21. Miyauchi M., Nishikawa A., Furukawa F., Nakamura H., Son H.-Y., Murakami A., Koshimizu K., Ohigashi H., Hirose M. 2000; Inhibitory effects of 1′-acetoxychavicol acetate on N -nitrosobis(2-oxopropyl)-amine-induced initiation of cholangiocarcinogenesis in Syrian hamsters. Jpn J Cancer Res 91:477–481 [CrossRef]
     [Google Scholar]
  22. Morita H., Itokawa H. 1988; Cytotoxic and antifungal diterpenes from the seeds of Alpinia galanga . Planta Med 54:117–120 [CrossRef]
     [Google Scholar]
  23. Murakami A., Ohura S., Nakamura Y., Koshimizu K., Ohigashi H. 1996; 1′-Acetoxychavicol acetate, a superoxide anion generator inhibitor, potently inhibits tumor promotion by 12- O -tetradecanoylphorbol-13-acetate in ICR mouse skin. Oncology 53:386–391 [CrossRef]
     [Google Scholar]
  24. Murakami N., Ye Y., Kawanishi M., Aoki S., Kudo N., Yoshida M., Nakayama E. E., Shioda T., Kobayashi M. 2002; New Rev-transport inhibitor with anti-HIV activity from Valerianae radix . Bioorg Med Chem Lett 12:2807–2810 [CrossRef]
     [Google Scholar]
  25. Najera I., Richman D. D., Olivares I., Rojas J. M., Peinado M. A., Perucho M., Najera R., López-Galíndez C. 1994; Natural occurrence of drug resistance mutations in the reverse transcriptase of human immunodeficiency virus type 1 isolates. AIDS Res Hum Retroviruses 10:1479–1488 [CrossRef]
     [Google Scholar]
  26. Ohnishi M., Tanaka T., Makita H. & 7 other authors 1996; Chemopreventive effect of a xanthine oxidase inhibitor, 1′-acetoxychavicol acetate, on rat oral carcinogenesis. Jpn J Cancer Res 87:349–356 [CrossRef]
     [Google Scholar]
  27. Palittapongarnpim P., Kirdmanee C., Kittakoop P., Rukseree K. 2002; 1′-Acetoxychavicol Acetate for Tuberculosis Treatment . US Patent Application no: 2002192262
     [Google Scholar]
  28. Pani A., Loi A. G., Mura M., Marceddu T., La Colla P., Marongiu M. E. 2002; Targeting HIV: old and new players. Curr Drug Targets Infect Disord 2:17–32 [CrossRef]
     [Google Scholar]
  29. Ratmeyer L., Zapp M. L., Green M. R., Vinayak R., Kumar A., Boykin D. W., Wilson W. D. 1996; Inhibition of HIV-1 Rev-RRE interaction by diphenylfuran derivatives. Biochemistry 35:13689–13696 [CrossRef]
     [Google Scholar]
  30. St Clair M. H., Martin J. L., Tudor-Williams G., Bach M. C., Vavro C. L., King D. M., Kellam P., Kemp S. D., Larder B. A. 1991; Resistance to ddI and sensitivity to AZT induced by a mutation in HIV-1 reverse transcriptase. Science 253:1557–1559 [CrossRef]
     [Google Scholar]
  31. Tanaka T., Kawabata K., Kakumoto M. & 8 other authors (1997a). Chemoprevention of azoxymethane-induced rat colon carcinogenesis by a xanthine oxidase inhibitor, 1′-acetoxychavicol acetate. Jpn J Cancer Res 88:821–830 [CrossRef]
     [Google Scholar]
  32. Tanaka T., Makita H., Kawamori T. & 7 other authors 1997b; A xanthine oxidase inhibitor 1′-acetoxychavicol acetate inhibits azoxymethane-induced colonic aberrant crypt foci in rats. Carcinogenesis 18:1113–1118 [CrossRef]
     [Google Scholar]
  33. Tözsér J. 2001; HIV inhibitors: problems and reality. Ann N Y Acad Sci 946:145–159
     [Google Scholar]
  34. Witvrouw M., van Maele B., Vercammen J., Hantson A., Engelborghs Y., de Clercq E., Pannecouque C., Debyser Z. 2004; Novel inhibitors of HIV-1 integration. Curr Drug Metab 5:291–304 [CrossRef]
     [Google Scholar]
  35. Wolff B., Sanglier J. J., Wang Y. 1997; Leptomycin B is an inhibitor of nuclear export: inhibition of nucleo-cytoplasmic translocation of the human immunodeficiency virus type 1 (HIV-1) Rev protein and Rev-dependent mRNA. Chem Biol 4:139–147 [CrossRef]
     [Google Scholar]
  36. Yoshikawa M., Matsuda H., Morikawa T. 2004; Antiallergy agent obtained from Alpinia galanga and method for production thereof . Jpn Kokai Tokkyo Koho patent no. 2004189669 (in Japanese
  37. Zapp M. L., Stern S., Green M. R. 1993; Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. Cell 74:969–978 [CrossRef]
     [Google Scholar]
  38. Zapp M. L., Young D. W., Kumar A., Singh R., Boykin D. W., Wilson W. D., Green M. R. 1997; Modulation of the rev-RRE interaction by aromatic heterocyclic compounds. Bioorg Med Chem 5:1149–1155 [CrossRef]
     [Google Scholar]
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1′S-1′-Acetoxychavicol acetate isolated from Alpinia galanga inhibits human immunodeficiency virus type 1 replication by blocking Rev transport
J. Gen. Virol. 87, 2047 (2006); https://doi.org/10.1099/vir.0.81685-0
/content/journal/jgv/10.1099/vir.0.81685-0
/content/journal/jgv/10.1099/vir.0.81685-0
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