Synthesis And Antifungal Activity Of Derivatives Of Prinsepiol

Lignans are widely existed in natural world with a variety of structures and bioactivities, including anti-tumor, anti-inflammation, anti-virus, anti-oxidation, protecting liver, lowering blood pressure, anti-allergy, sedation, as well as seed-germination inhibitor, growth inhibitor, insecticide, fungicide. Our previous research showed that Prinsepiol had better antimicrobial activity, For further study, This paper takes Prinsepiol as parent compounds, derivatively synthesized series of Prinsepiol derivatives; tested antibacterial activity of the derivatives. The results showed as follows:1. 13 Prinsepiol derivatives were obtained and their structures had been confirmed by IR, UV, 1H- NMR, 13C- NMR and HRMS, 13 derivatives were proved new compounds after literatures studying.2. 13 Prinsepiol derivatives have the inhibitory effects to the spore germination of Botrytis cirerea. Except 4, 4′- Dibenzenesulfonyl derivatives , the other 12 synthesized compounds respectively have somewhat advantage in inhibition which compared with Prinsepiol. Of which 4, 4′- Diisobutyryl and 4, 4′- Diacetyl derivatives exhibited highest activities with EC50 of 3.85 mg/L and 5.60 mg/L, 6 ~ 8 times higher than that of Prinsepiol respectively.3. 13 Prinsepiol derivatives have the inhibitory effects on the spore germination of Exserohilum turcicum. Except 4, 4′- Dibenzenesulfonyl derivatives, the other 12 synthesized compounds respectively have somewhat advantage in inhibition which compared with Prinsepiol. Of which 4, 4′- Diisobutyryl and 4, 4′- Dipropiony1 derivatives exhibited highest activities with EC50 of 4.68 mg/L and 8.52 mg/L, 6 ~ 9 times higher than that of Prinsepiol respectively.4. 4, 4′- Dibenzenesulfonyl derivatives had lower activity than Prinsepiol, nevertheless, the other 12 synthesized compounds had higher activities compared with Prinsepiol. The activity of introducing two functional groups to 4, 4'hydroxyls is better than introducing one, introducing branched chain groups is better than straight chain group, the length of the acyl-carbochain can affect the activity of derivatives compounds. The parent compound of all the 13 4, 4′hydroxyls derivatives compounds is Prinsepiol, form which no 8, 8′hydroxyls derivatives compounds was synthesized. We cannot confirm the active center of these derivatives at present, but we find that the 4, 4′of Prinsepiol has obvious relationship with its bioactivity. It worth further research on Prinsepiol structure-activity relationship and the confirmation of its active center.