Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 15, Pages 5676-5682Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.06.010
Keywords
Lignans; Oxidation; Methyltrioxorhenium; Antioxidant activity; Apoptogenic activity
Funding
- Interuniversity Consortium 'Chemistry for the Environment' (INCA)
- PNR-FIRB
- ASI and EU COST CM07035 System
- Academy of Finland
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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.
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