title: Isopimarane diterpenoids from Kaempferia pulchra rhizomes collected in Myanmar and their Vpr inhibitory activity.
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 6.25μM. 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.
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan; Department of Chemistry, University of Yangon, Yangon 11041, Myanmar.
authors.forename: Nwet Nwet
authors.initials: NN
authors.lastname: Win
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Ito
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsui
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Simayijiang
authors.initials: S
authors.lastname: Aimaiti
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kodama
authors.affiliation: Department of Chemistry, University of Yangon, Yangon 11041, Myanmar.
authors.forename: Hla
authors.initials: H
authors.lastname: Ngwe
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Okamoto
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Masami
authors.initials: M
authors.lastname: Tanaka
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Asakawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Ikuro
authors.initials: I
authors.lastname: Abe
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Morita
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D016336:Gene Products, vpr / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015658:HIV Infections / Q000188:drug therapy / Q000821:virology; D015497:HIV-1 / Q000187:drug effects* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D027343:Rhizome / Q000737:chemistry; D013329:Structure-Activity Relationship; D030521:Zingiberaceae / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D004224:Diterpenes; D016336:Gene Products, vpr
keywords: Anti-Vpr; Kaempferia pulchra; Kaempulchraols; TREx-HeLa-Vpr cells