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Dendrogenin A arises from cholesterol and histamine metabolism and shows cell differentiation and anti-tumour properties

Author

Listed:
  • Philippe de Medina

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    AFFICHEM)

  • Michael R. Paillasse

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    AFFICHEM)

  • Gregory Segala

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    University Toulouse III
    Institut Claudius Regaud)

  • Maud Voisin

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    University Toulouse III
    Institut Claudius Regaud)

  • Loubna Mhamdi

    (AFFICHEM)

  • Florence Dalenc

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    University Toulouse III
    Institut Claudius Regaud)

  • Magali Lacroix-Triki

    (University Toulouse III
    Institut Claudius Regaud)

  • Thomas Filleron

    (Institut Claudius Regaud)

  • Frederic Pont

    (UDEAR, UMR 5165 CNRS-University Toulouse III
    France)

  • Talal Al Saati

    (INSERM-US006 ANEXPLO/CREFRE)

  • Christophe Morisseau

    (University of California)

  • Bruce D. Hammock

    (University of California)

  • Sandrine Silvente-Poirot

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    University Toulouse III
    Institut Claudius Regaud)

  • Marc Poirot

    (INSERM UMR 1037, Team ‘Sterol Metabolism and Therapeutic Innovations in Oncology’, Cancer Research Center of Toulouse
    University Toulouse III
    Institut Claudius Regaud)

Abstract

We previously synthesized dendrogenin A and hypothesized that it could be a natural metabolite occurring in mammals. Here we explore this hypothesis and report the discovery of dendrogenin A in mammalian tissues and normal cells as an enzymatic product of the conjugation of 5,6α-epoxy-cholesterol and histamine. Dendrogenin A was not detected in cancer cell lines and was fivefold lower in human breast tumours compared with normal tissues, suggesting a deregulation of dendrogenin A metabolism during carcinogenesis. We established that dendrogenin A is a selective inhibitor of cholesterol epoxide hydrolase and it triggered tumour re-differentiation and growth control in mice and improved animal survival. The properties of dendrogenin A and its decreased level in tumours suggest a physiological function in maintaining cell integrity and differentiation. The discovery of dendrogenin A reveals a new metabolic pathway at the crossroads of cholesterol and histamine metabolism and the existence of steroidal alkaloids in mammals.

Suggested Citation

  • Philippe de Medina & Michael R. Paillasse & Gregory Segala & Maud Voisin & Loubna Mhamdi & Florence Dalenc & Magali Lacroix-Triki & Thomas Filleron & Frederic Pont & Talal Al Saati & Christophe Moriss, 2013. "Dendrogenin A arises from cholesterol and histamine metabolism and shows cell differentiation and anti-tumour properties," Nature Communications, Nature, vol. 4(1), pages 1-10, October.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms2835
    DOI: 10.1038/ncomms2835
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