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Antifungal drug
Hinokinin
Другие языки:

    Hinokinin

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    Hinokinin
    Hinokinin.png
    Names
    Preferred IUPAC name
    (3R,4R)-3,4-Bis[(2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one
    Other names
    (3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)dihydro-2(3H)-furanone
    Identifiers
    3D model (JSmol)
    ChEMBL
    ChemSpider
    PubChem CID
    • InChI=1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1 checkY
      Key: DDWGQGZPYDSYEL-LSDHHAIUSA-N checkY
    • InChI=1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1
      Key: DDWGQGZPYDSYEL-LSDHHAIUSA-N
    • C1C(C(C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
    Properties
    C20H18O6
    Molar mass 354.358 g·mol−1
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
    checkY verify (what is checkY☒N ?)

    Hinokinin is a dibenzylbutyrolactone lignan, derived from various species of plants. It is a potential antichagonistic agent and has shown to possess neuroprotective effects as well. It is also found to have anti-inflammatory, anti-cancer, antiviral and antifungal properties.

    Hinokinin was isolated for the first time by Yoshiki and Ishiguro in 1933 from hinoki wood.

    Chemical properties

    Hinokinin is a colourless crystalline compound.

    It can be isolated from various species of Chamaecyparis, Zanthoxylum, Phyllanthus, Aristolochia, Piper, Virola, Linum and Bursera. It is also synthesised from pinoresinol.

    Biological effects

    Cytotoxic actions

    Hinokinin has shown to induce apoptosis and promote antitumor actions on various cancer cell lines in vitro.

    Anti-inflammatory actions

    Hinokinin has been shown to inhibit the generation of superoxide molecules by neutrophils and also decreases elastase secretion from neutrophils. It has also shown to reduce LPS induced nitric oxide production from macrophages.The anti-inflammatory property of hinokinin is mediated by the NF-kB signalling mechanism.

    Anti-parasitic actions

    Hinokinin has been shown to be an antitrypanosomal agent. Its use as a treatment for trypanosomiasis is still being researched.

    Anti-viral actions

    It has shown significant antiviral activity against human hepatitis B virus, HIV and SARS-CoV.

    See also


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