Isolation and structure of vanitaracin A, a novel anti-hepatitis B virus compound from Talaromyces sp.
Two new tricyclic polyketides, vanitaracin A (1) and B (2), together with three novel compounds 3, 4 and 5, were isolated from a culture broth of a fungus, Talaromyces sp. The chemical structures of these compounds were determined from spectroscopic data (1D/2D NMR, MS and IR). The five isolated compounds were then tested for anti-hepatitis B virus (HBV) activity and vanitaracin A was found to exhibit an IC50 value of 10.5 μM using a HBV-susceptible cell line. By contrast, the derivative 2 displayed weak anti-HBV action, which suggested that the substituents at C-9 in 1 are likely to be important for its antiviral activity. We believe the two vanitaracin derivatives constitute a new class of anti-HBV agents.
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan.
Hiroki
H
Matsunaga
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan.
Shinji
S
Kamisuki
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan; Department of Virology II, National Institute of Infectious Diseases, Shinjuku-ku, Tokyo 162-8640, Japan.
Manabu
M
Kaneko
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan.
Yasuhiro
Y
Yamaguchi
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan.
Toshifumi
T
Takeuchi
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan; Department of Virology II, National Institute of Infectious Diseases, Shinjuku-ku, Tokyo 162-8640, Japan.
Koichi
K
Watashi
Department of Applied Biological Science, Tokyo University of Sciences, Noda, Chiba 278-8510, Japan. Electronic address: sugawara@rs.noda.tus.ac.jp.
Fumio
F
Sugawara
D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D056945:Hep G2 Cells; D006515:Hepatitis B virus / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D032901:Talaromyces / Q000737:chemistry*
D000998:Antiviral Agents; D061065:Polyketides; C000605351:vanitaracin A
HBV; Infection; Natural products; Structure determination