A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity

Roberta Bernini, Giampiero Gualandi, Claudia Crestini, Maurizio Barontini, Maria Cristina Belfiore, Stefan Willför, Patrik Christoffer Eklund, Raffaele Saladino

    Research output: Contribution to journalArticleScientificpeer-review

    16 Citations (Scopus)

    Abstract

    Highly oxidized lignans produced during the cytochrome P-450 metabolism in the cells show biological activities significantly different from those of their parent natural compounds. Lignans precursors of mammalian enterolignans were treated with a methyltrioxorhenium/hydrogen peroxide catalytic system to afford new compounds oxidized at benzylic as well as in arylic positions. The evaluation of the antioxidant and apoptogenic activity by in vivo protocols of these compounds showed some interesting structure-activity relationships related to the oxidation degree of the molecules. (C) 2009 Elsevier Ltd. All rights reserved.
    Original languageUndefined/Unknown
    Pages (from-to)5676–5682
    Number of pages7
    JournalBioorganic and Medicinal Chemistry
    Volume17
    Issue number15
    DOIs
    Publication statusPublished - 2009
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Antioxidant activity
    • Apoptogenic activity
    • Lignans
    • Methyltrioxorhenium
    • Ethanol Oxidation

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