Eucryphin analog's total synthesis, anti-inflammatory activity for DNFB-induced contact hypersensitivity and structure-activity relationship

Eucryphin, a natural product widely found in plants, has a variety of biological activities. In this work, a series of eucryphin analogs were designed, synthesized, characterized and the anti-inflammatory activity in vivo was evaluated comparing with eucryphin and its 7-O-glycosyl derivatives to study the structure-activity relationship. Eucryphin exhibited remarkable anti-inflammatory activity and minor side effects in 2,4-dinitrofluorobenzene (DNFB) induced mice auricle edema model. Glycosyl substitution at the position of C-3 was essential for the anti-inflammatory activity. Methyl substitution at C-2 and glycosylation at C-7 of eucryphin reduce anti-inflammatory activity.

Automated summary

In this study, a series of eucryphin analogs were synthesized and compared with eucryphin and its 7-O-glycosyl derivatives for their anti-inflammatory activity, revealing the importance of glycosyl substitution at the C-3 position and the negative effect of methyl substitution at C-2 and glycosylation at C-7 on the anti-inflammatory activity of eucryphin.