Chemical studies on antioxidant mechanisms and free radical scavenging properties of lignans

被引:165
作者
Eklund, PC
Långvik, OK
Wärnå, JP
Salmi, TO
Willför, SM
Sjöholm, RE
机构
[1] Abo Akad Univ, Proc Chem Ctr, Dept Organ Chem, FIN-20500 Turku, Finland
[2] Abo Akad Univ, Proc Chem Ctr, Lab Ind Chem, FIN-20500 Turku, Finland
[3] Abo Akad Univ, Proc Chem Ctr, Lab Wood & Paper Chem, FIN-20500 Turku, Finland
关键词
D O I
10.1039/b506739a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The antioxidant activity, in terms of radical scavenging capacity, of altogether 15 different lignans was measured by monitoring the scavenging of the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). The effect of differences in skeletal arrangement or the degree of oxidation of the lignans was investigated in a structure-activity relationship study. A large variety in the radical scavenging capacities of the different lignans was observed and related to some structural features. Lignans with catechol (3,4-dihydroxyphenyl) moieties exhibited the highest radical scavenging capacity, while the corresponding guaiacyl ( 3-methoxy-4-hydroxyphenyl) lignans showed a slightly weaker scavenging capacity. In addition, the butanediol structure was found to enhance the activity, whereas a higher degree of oxidation at the benzylic positions decreased the activity. Additionally, the readily available lignans (-)-secoisolariciresinol, a mixture of hydroxymatairesinol epimers and (-)- matairesinol were studied in more detail, including kinetic measurements and identification of oxidation products in the reactions with DPPH and ABAP (2,2-azobis(2-methylpropionamidine) dihydrochloride. The identification of reaction products, by GC-MS, HPLC-MS and NMR spectroscopy, showed that dimerisation of the two aromatic moieties was the major radical termination reaction. Also, the formation of adducts was a predominant reaction in the experiments with ABAP. The kinetic data obtained from the reactions between the lignans and DPPH indicated a complex reaction mechanism.
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页码:3336 / 3347
页数:12
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