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Chemical modification and anticancer effect of prenylated flavanones from Taiwanese propolis.

Abstract

Our previous studies demonstrated that eight prenylated flavanones (1-8), isolated from Taiwanese propolis, were capable of a broad spectrum of biological activities. Among them, nymphaeol A (3), nymphaeol B (4) and nymphaeol C (7), abundant in Taiwanese propolis, exhibited cytotoxicity against cancer cell lines. It therefore seemed interesting to improve their activity via a semi-synthetic strategy. In this study, 12 novel prenylated flavanones were synthesised in our laboratory and their activities were assessed for two human prostate cancer cell lines, PC-3 and DU-145, and a human hepatoma cell line, Hep-3B. Of these compounds, 10c, 11 and 12 showed more potent cytotoxicity against the PC-3 cell line than 5-Fu. Using cytometric analysis followed by double staining with annexin V-FITC and propidium iodide, it was observed that these compounds induced apoptosis as well. This suggests that prenylated flavanones 10c, 11 and 12 may have anticancer potential for further development.

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  • Authors+Show Affiliations

    ,

    NatureWise Biotech & Medicals Corporation, Taipei 115, Taiwan.

    , , , , ,

    Source

    Natural product research 26:2 2012 pg 116-24

    MeSH

    Antineoplastic Agents
    Apoptosis
    Carcinoma, Hepatocellular
    Cell Line, Tumor
    Drug Discovery
    Flavanones
    Flow Cytometry
    Humans
    Liver Neoplasms
    Magnetic Resonance Spectroscopy
    Male
    Molecular Structure
    Prenylation
    Propolis
    Prostatic Neoplasms
    Taiwan

    Pub Type(s)

    Journal Article
    Research Support, Non-U.S. Gov't

    Language

    eng

    PubMed ID

    21790499

    Citation

    TY - JOUR T1 - Chemical modification and anticancer effect of prenylated flavanones from Taiwanese propolis. AU - Chen,Chia-Nan, AU - Hsiao,Che-Jen, AU - Lee,Shoei-Sheng, AU - Guh,Jih-Hwa, AU - Chiang,Po-Cheng, AU - Huang,Chih-Chiang, AU - Huang,Wei-Jan, Y1 - 2011/07/27/ PY - 2011/7/27/aheadofprint PY - 2011/7/28/entrez PY - 2011/7/28/pubmed PY - 2012/4/10/medline SP - 116 EP - 24 JF - Natural product research JO - Nat. Prod. Res. VL - 26 IS - 2 N2 - Our previous studies demonstrated that eight prenylated flavanones (1-8), isolated from Taiwanese propolis, were capable of a broad spectrum of biological activities. Among them, nymphaeol A (3), nymphaeol B (4) and nymphaeol C (7), abundant in Taiwanese propolis, exhibited cytotoxicity against cancer cell lines. It therefore seemed interesting to improve their activity via a semi-synthetic strategy. In this study, 12 novel prenylated flavanones were synthesised in our laboratory and their activities were assessed for two human prostate cancer cell lines, PC-3 and DU-145, and a human hepatoma cell line, Hep-3B. Of these compounds, 10c, 11 and 12 showed more potent cytotoxicity against the PC-3 cell line than 5-Fu. Using cytometric analysis followed by double staining with annexin V-FITC and propidium iodide, it was observed that these compounds induced apoptosis as well. This suggests that prenylated flavanones 10c, 11 and 12 may have anticancer potential for further development. SN - 1478-6427 UR - https://www.unboundmedicine.com/medline/citation/21790499/full_citation/Chemical_modification_and_anticancer_effect_of_prenylated_flavanones_from_Taiwanese_propolis_ L2 - http://www.tandfonline.com/doi/abs/10.1080/14786419.2010.535146?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub=pubmed ER -