Effect of the Benzylic Structure of Lignan on Antioxidant Activity

Abstract

The effect of the benzylic structure of lignan on antioxidant activity was evaluated. Secoisolariciresinol (1) and 3,4-bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (2), which have two secondary benzylic positions without oxygen, showed the highest antioxidant activity. Optically active verrucosin (4) was synthesized for the first time in this experiment.

Isochaihulactone protects PC12 cell against H2O2 induced oxidative stress and exerts the potent anti-aging effects in D-galactose aging mouse model

“…Results [34,35] . The chemical structure of isochaihulactone (sugar moiety attached to the 20 position of the triterpene dammarane) may contribute to its direct antioxidant properties [36] .…”

Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7′-Oxodihydroguaiaretic Acid

“…The same results have previously been shown as for the tetrahydrofuran-type of lignans. 3,5) These results suggest that the oxygen-free benzylic position of lignans is more important for the chemical antioxidant activity than the phenolic group. Even when the p-phenolic group was present, the higher oxidation degree at the benzylic position decreased the antioxidant activity.…”

“…This result is same as that from a previous study on tetrahydrofuran and butyrolactone lignans. [3][4][5] It could be assumed that the oxygen-free benzylic position of lignan is important for the reaction with DPPH. In the test for production of ethyl linoleate hydroperoxide, (À)-DGA and (À)-SECO were stronger inhibitors of the production of hydroperoxide than (+)-ODGA (Fig.…”

“…In our previous study, the higher degree of benzylic oxidation of tetrahydrofuran and butyrolactone lignan decreased the antioxidant activity. [3][4][5] The purpose of this research on butane-type lignans is to determine the effect of benzylic oxidation on the antioxidant activity. As well as the chemical antioxidant activity, the lipoxygenase inhibition activities of both enantiomers of SECO, DGA and ODGA were evaluated in this study (Fig.…”

First Stereoselective Synthesis ofmeso-Secoisolariciresinol and Comparison of Its Biological Activity with (+) and (−)-Secoisolariciresinol

“…Fax: +81-89-977-4364; E-mail: syamauch@agr.ehime-u.ac.jp the previously reported method. 18 Determination of the enantiomeric excess of SECO-1 and SECO-2. A reaction solution of (+)-secoisolariciresinol (SECO-1) (25 mg, 0.069 mmol) in pyridine (0.1 ml) and Ac 2 O (0.1 ml) containing DMAP (1 mg) was stood at room temperature for 16 h before addition of ice.…”