Evaluation of antioxidant properties of monoaromatic derivatives of pulvinic acids.
The natural mushroom pigment Norbadione A and three other pulvinic acids were shown by our group to display very efficient antioxidant properties by comparison with a collection of potent molecules including catechols, flavonoids, stilbenes, or coumarins. Despite numerous publications on robust and straightforward synthetic access to pulvinic acids by us and others, no report has been made to unravel the structure-activity relationships that govern the striking antioxidant activity. Herein is presented the synthesis of 18 diverse pulvinic acid derivatives and the study of their radical scavenging capacities by four different assays. The influence of each of the two phenyl rings, of their substituents and of the lateral chain on the antioxidant properties, was explored to reveal a simplified structure of excellent activity. These results, along with the absence of cytotoxicity, make the synthesized compounds interesting to evaluate for several biological activities and especially for anti-inflammatory effects and skin protection against UV induced oxidative stress.
Habrant
Damien
D
Laboratoire de Synthese Bio-Organique, CNRS-UMR 7175/LC1, Institut Gilbert Laustriat, Faculte de Pharmacie, Illkirch, 67401 France.
Poigny
Stéphane
S
Ségur-Derai
Muriel
M
Brunel
Yves
Y
Heurtaux
Benoît
B
Le Gall
Thierry
T
Strehle
Axelle
A
Saladin
Régis
R
Meunier
Stéphane
S
Mioskowski
Charles
C
Wagner
Alain
A
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D016466:CHO Cells; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D006224:Cricetinae; D003412:Cricetulus; D004278:DNA, Superhelical / Q000737:chemistry; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D018384:Oxidative Stress; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000737:chemistry; D013936:Thymidine / Q000737:chemistry; D014466:Ultraviolet Rays / Q000009:adverse effects
D000975:Antioxidants; D002264:Carboxylic Acids; D004278:DNA, Superhelical; D016166:Free Radical Scavengers; D007783:Lactones; D013481:Superoxides; C492654:pulvinic acid; D013936:Thymidine