The IgE-suppressive activity of (À)-matairesinol is demonstrated, and the structure-activity relationship of (À)-matairesinol clarified. 3 0 ,4-Dihydroxy-3,4 0 -dimethoxylignano-9,9 0 -lactone showed higher IgE-suppressive activity than (À)-matairesinol without any cytotoxic activity. Some derivatives bearing a longer and more bulky alkoxy group at the 3 or 4 position showed IgEaccelerative activity.Key words: lignan; matairesinol; IgE-suppressive activity (À)-Matairesinol, ,-dibenzyl--butyrolactone lignan, is one of the well-known lignans contained in food plant.1-4) Although many ,-dibenzyl--butyrolactone lignans have been isolated from plants, 5) a detailed study on the relationship between the structure and biological activity and the effect of the stereochemistry on the biological activity has not been conducted. Our interest is the chemical function of the food plant and the structure-activity relationship of the biologically active compounds contained in the food plant. Antibody-productive activity was selected to clarify the effect of food plants on the human health in this study. Since the biosynthesis as an enantiomeric mixtures has been reported in the biosynthetic research on lignan, 6) (À)-matairesinol and its stereoisomers were examined at first, and then the derivatives were applied to the biological testing. The stereoisomers of matairesinol and derivatives were synthesized by the previously described method.7-10) Since IgE is an antibody for allergy, suppressing the activity of IgE-production would decrease the allergic symptoms, while promotive compounds would contribute to research into allergy. The IgM-and IgE-productive activities of secoisolariciresinol, which is a butanediol type of lignan contained in food plant, were examined in our previous study, and the IgM-accelerative production of (À)-and (þ)-secoisolariciresinol was observed; however, none of the stereoisomers of secoisolariciresinol affected the IgE-productive activity.11) In this article, the IgEproductive activity of four stereoisomers of matairesinol is compared, and the structure-activity relationship of (À)-matairesinol is described. The results of this study should contribute to the development of new medicines and the utilization of natural resources.
Material and MethodsMelting point (mp) data are uncorrected. NMR data were measured by a JNM-EX400 spectrometer, using TMS as a standard (0 ppm), MS data were measured with a JMS-MS700V spectrometer, and optical rotation values were evaluated with a Horiba SEPA-200 instrument. The nomenclature of compounds follows the literature for lignans.
12)All stereoisomers and derivatives were prepared by the previously described method.7-10) The enantiomeric excess of all stereoisomers of matairesinol prepared by the previous method was determined as more than 99%ee by using a chiral column. 9,13)