Isopimarane diterpenoids from Kaempferia pulchra rhizomes collected in Myanmar and their Vpr inhibitory activity

Nwet Nwet Win, Takuya Ito, Takashi Matsui, Simayijiang Aimaiti, Takeshi Kodama, Hla Ngwe, Yasuko Okamoto, Masami Tanaka, Yoshinori Asakawa, Ikuro Abe, Hiroyuki Morita

    Research output: Contribution to journalArticlepeer-review

    25 Citations (Scopus)

    Abstract

    Viral protein R (Vpr), an accessory gene of HIV-1, plays important roles in viral pathogenesis. Screening of Myanmar medicinal plants that are popular as primary treatments for HIV/AIDS and for HIV-related problems revealed the potent anti-Vpr activity of the CHCl3-soluble extract of Kaempferia pulchra rhizomes, in comparison with that of the positive control, damnacanthal. Fractionation of the active CHCl3-soluble extract led to the identification of 30 isopimarane diterpenoids, including kaempulchraols A–W (1–23). All isolates were assayed for anti-Vpr activity against TREx-HeLa-Vpr cells, in which Vpr expression is tightly regulated by tetracycline. Kaempulchraols B (2), D (4), G (7), Q (17), T (20), U (21), and W (23) exhibited potent anti-Vpr activity, at concentrations ranging from 1.56 to 6.25 μM. The structure–activity relationships of the active kaempulchraols suggested that the presence of a hydroxy group at C-14 in an isopimara-8(9),15-diene skeleton and the presence of an acetoxy group at C-1 or C-7 in an isopimara-8(14),15-diene skeleton are the critical factors for the inhibitory effects against TREx-HeLa-Vpr cells.

    Original languageEnglish
    Pages (from-to)1789-1793
    Number of pages5
    JournalBioorganic and Medicinal Chemistry Letters
    Volume26
    Issue number7
    DOIs
    Publication statusPublished - 2016

    Keywords

    • Anti-Vpr
    • Kaempferia pulchra
    • Kaempulchraols
    • TREx-HeLa-Vpr cells

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Medicine
    • Molecular Biology
    • Pharmaceutical Science
    • Drug Discovery
    • Clinical Biochemistry
    • Organic Chemistry

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