Preventive Agents against Sepsis and New Phenylpropanoid Glucosides from the Fruits of Illicium verum

Abstract

The bioassay-guided fractionation of preventive agents against lethality due to septic shock from the fruits of Illicium verum led to the isolation of two known racemic mixtures of phenylpropanoids, [1-(4′-methoxyphenyl)-(1R,2S and 1S,2R)-propanediol (1) and 1-(4′-methoxyphenyl)-(1R,2R and 1S,2S)-propanediol (2)], along with two known phenylpropanoid glucosides, [1-(4′-methoxyphenyl)-(1S,2R)-propan-1-ol 2-O-β-D-glucopyranoside (3) and 1-(4′-methoxyphenyl)-(1R,2S)-propan-1-ol 2-O-β-D-glucopyranoside (5)], and two new phenylpropanoid glucosides, [1-(4′-methoxyphenyl)-(1S,2S)-propan-1-ol 2-O-β-D-glucopyranoside (4) and 1-(4′-methoxyphenyl)-(1R,2R)-propan-1-ol 2-O-β-D-glucopyranoside (6)]. Their chemical structures were elucidated on the basis of spectroscopic studies. Among them, 1 exhibited the highest survival rate in a dose-dependent manner (100 % with a dose of 10 mg/kg against 40 % for the control experiment) and showed a reduction of the plasma alanine aminotransferase (ALT) value on the in vivo assay model of septic shock induced by tumor necrosis factor (TNF)-α.

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