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A spectroelectrochemical and chemical study on oxidation of 7,8-dihydroxy-4-methylcoumarin (DHMC) and some related compounds in aprotic medium

  1. Author:
    Petrucci, R.
    Saso, L.
    Kumar, V.
    Prasad, A. K.
    Malhotra, S. V.
    Parmar, V. S.
    Marrosu, G.

  2. Author Address

    [Petrucci, Rita; Marrosu, Giancarlo] Univ Roma La Sapienza, Dipartimento Ingn Chim Mat Ambiente, I-00161 Rome, Italy. [Saso, Luciano] Univ Roma La Sapienza, Dipartimento Fisiol & Farmacol Vittorio Erspamer, I-00185 Rome, Italy. [Kumar, Vineet; Prasad, Ashok K.; Parmar, Virinder S.] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India. [Kumar, Vineet; Malhotra, Sanjay V.] Natl Canc Inst Frederick, Lab Synthet Chem, Dev Therapeut Program Support, SAIC Frederick, Frederick, MD 21702 USA.;Petrucci, R, Univ Roma La Sapienza, Dipartimento Ingn Chim Mat Ambiente, Via Castro Laurenziano 7, I-00161 Rome, Italy.;rita.petrucci@uniroma1.it
    1. Year: 2010
    2. Date: Sep
  2. Journal: Biochimie
    1. 92
    2. 9
    3. Pages: 1123-1129
  4. Type of Article: Article
  5. ISSN: 0300-9084
  1. Abstract:

    Electrochemical and chemical oxidation of 7,8-hydroxy-4-methylcoumarin (DHMC 1) and 7,8-diacetoxy-4-methylcoumarin (DAMC 4) were studied to investigate the mechanisms occurring in their antioxidant activities in acetonitrile, under electron transfer and H-atom transfer conditions. Electrolysis and chemical reactions were followed on-line by monitoring the UV spectral changes with time. The anodic oxidation of DHMC, studied by cyclic voltammetry and controlled potential electrolysis, occurs via a reversible one-step two-electrons process, yielding the corresponding stable phenoxonium cation. Moreover, the chemical oxidation with an H-atom acceptor also follows a similar path, yielding the stable neutral quinonic product. Intermediates were never evidenced in both cases. Only in the presence of a strong base, an anodic oxidation product mono-electronic was evidenced, likely the DHMC radical anion. However, the anodic oxidation of the acetoxy derivative DAMC occurs at very high potential values, ruling out the possibility that the antioxidant activity observed in vivo might occur via an electron transfer mechanism; no reactions were evidenced with an H-atom acceptor. (C) 2010 Elsevier Masson SAS. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.biochi.2010.06.008
  3. View record in Web of Science®
  4. WOS: 000281991400006

Library Notes

  1. Fiscal Year: FY2009-2010
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