(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one

Description

The roots of Sternona japonica contain this complex alkaloid which forms colourless crystals from MeOH containing solvent of crystallization. The base is dextrorotatory with [α]_D + 147.8° and the ultraviolet spectrum shows a broad absorption maximum at 305 m/J.. The picrolonate has been prepared as yellow needles, m.p. 237°C. The structure given above is based upon X-ray crystallo_x0002_graphic analysis of the MeOH solvate and on the already established configuration of Stemonine (q.v.).

The Uses of (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one

Protostemonine is an alkaloid which provided protective effects of protostemonine in LPS/GalN-induced acute liver failure.

Definition

ChEBI: Protostemonine is an alkaloid. It has a role as a metabolite.

References

Kondo, Satomi.,J. Pharrn. Soc., Japan, 67, 182, 185, 188 (1947)
Structure: Irie et al., Chern. Pharrn. Bull., 21, 451 (1973)