Chemical and Biochemical Modifications of Parthenin

Article abstract of DOI:10.1016/S0040-4020(99)00292-6

Parthenin, a medicinally important natural sesquiterpenoid and a potent allelochemical underwent different regio- and stereoselective modifications to several interesting analogues by chemical and biochemical means. The compound was treated with various common reducing agents including NaBH4, NaBH4/I2, Na/EtOH, Mg/MeOH and Zn/HOAc as well as with different oxidizing agents including m-CPBA and dilute HCl under different reaction conditions. The retention of the α-methylene-γ-lactone moiety which plays a vital role for bioactivity of the compound was observed in some of the reaction products. The microwave irradiation of the compound afforded anhydroparthenin as the only product. Baker's yeast reduction of parthenin was investigated for the first time and yielded the naturally occurring dihydrocoronopilin. - Keywords: parthenin, sesquiterpenoid, α-methylene-γ-lactone, chemical modifications, baker's yeast reduction.