Synthesis and antioxidant properties of a new lipophilic ascorbic acid analogue.
4-(4-Hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-2-hydroxyfurane-2-one 1 was prepared by an acidic dimerisation of 4-hydroxyphenylpyruvic acid and some of its antioxidant and spectroscopic properties have been measured and compared to that of ascorbic acid. 1 is as good an antioxidant as ascorbic acid in the DPPH (2,2-diphenyl-1-picryl hydrazyl radical) test and the inhibition of hydroxyl radical and a powerful inhibitor of the Cu(2+) or AAPH (2,2'-azobis-(2-amidinopropane) dihydrochloride) induced oxidation of human LDL. 1 gives a stable radical characterised by its ESR spectrum similarly to ascorbic acid but in lower concentration and with a different reactivity towards nitroxides. Theoretical calculations allow us to propose the structure for the radical formed from 1, to explain its lower stability than ascorbyl radical and to evaluate the lipophilicity of 1.
Cotelle
Philippe
P
Laboratoire de Chimie Organique et Macromoléculaire, UPRESA CNRS 8009, Université des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq, France. philippe.cotelle@univ-lille1.fr
Cotelle
Nicole
N
Teissier
Elisabeth
E
Vezin
Hervé
H
D000578:Amidines / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D001713:Biphenyl Compounds; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D008078:Cholesterol, LDL / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D004574:Electromagnetic Fields; D004578:Electron Spin Resonance Spectroscopy; D005663:Furans / Q000138:chemical synthesis*; D006801:Humans; D017665:Hydroxyl Radical / Q000737:chemistry; D007202:Indicators and Reagents; D008055:Lipids / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010851:Picrates / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
C478829:4-(4-Hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-2-hydroxyfurane-2-one; D000578:Amidines; D000975:Antioxidants; D001713:Biphenyl Compounds; D008078:Cholesterol, LDL; D005663:Furans; D007202:Indicators and Reagents; D008055:Lipids; D010851:Picrates; D017665:Hydroxyl Radical; C046728:2,2'-azobis(2-amidinopropane); D003300:Copper; C004931:1,1-diphenyl-2-picrylhydrazyl; D001205:Ascorbic Acid