Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans
- 3 September 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 68 (10), 1459-1470
- https://doi.org/10.1021/np050089s
Abstract
It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding γ-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy-3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1−9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.Keywords
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