An HIV RNase H Inhibitory 1,3,4,5-Tetragalloylapiitol from the African Plant Hylodendron gabunensis

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 10; pp. 1647 - 1649
• Main Authors: Takada, Kentaro, Bermingham, Alun, O’Keefe, Barry R, Wamiru, Antony, Beutler, John A, Le Grice, Stuart F. J, Lloyd, John, Gustafson, Kirk R, McMahon, James B
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.10.2007; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 1,3,4,5-tetragalloylapiitol; Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; apiitol; Biological and medical sciences; Cameroon; chemical structure; Chemistry, Medicinal; enzyme inhibition; erythritol; Erythritol - analogs & derivatives; Erythritol - chemistry; Erythritol - isolation & purification; Erythritol - pharmacology; Escherichia coli; Fabaceae - chemistry; General pharmacology; HIV-1 - drug effects; HIV-2 - drug effects; Human immunodeficiency virus 1; Human immunodeficiency virus 2; Humans; Hylodendron; Hylodendron gabunensis; Inhibitory Concentration 50; Life Sciences & Biomedicine; Medical sciences; medicinal properties; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Leaves - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Ribonuclease H - antagonists & inhibitors; ribonucleases; Science & Technology; spectral analysis; Africa; Cameroon; ANGSTROM RESOLUTION; APIOSE; CRYSTAL-STRUCTURE; DNA; REVERSE-TRANSCRIPTASE; HIV-1 virus; Phenolic acid; Esterases; Extract; NMR spectrometry; Medicinal plant; Polyphenol; Dicotyledones; Angiospermae; Inhibition; Human; Enzyme; Pharmacognosy; Retroviridae; Enzyme inhibitor; Calf thymus ribonuclease H; Lentivirus; In vitro; Biological activity; HIV-2 virus; Virus; Hydrolysis; Alditol; Leguminosae; Absolute configuration; Plant origin; Hydrolases; Isolation; Spermatophyta; Human immunodeficiency virus; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0702279

A new compound, 1,3,4,5-tetragalloylapiitol (1), was isolated from the aqueous extract of the plant Hylodendron gabunensis and was found to be a potent inhibitor of RNase H enzymatic activity. The structure of 1 was elucidated by NMR analyses to be an apiitol (2) sugar moiety substituted with four gallic acid residues. Optical rotation measurements of the free sugar following basic hydrolysis indicated that the 3S absolute configuration was the same as that of d-apiitol. Compound 1 inhibited HIV-1, HIV-2, and human RNase H with IC50 values of 0.24, 0.13, and 1.5 µM, respectively, but it did not show inhibition of E. coli RNase H at 10 µM.