New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Nat Prod Bioprospect. 2019 Jun;9(3):231-241. doi: 10.1007/s13659-019-0208-z. Epub 2019 May 9.

Abstract

Two new amides (E)-N-cinnamoyl-2-methoxypiperidine (1) and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one (2), four new amide glucosides, retrofractosides A-D (3-6), and two new phenylpropanoid glucosides, retrofractosides E (7) and F (8), together with 24 known compounds (9-32) were isolated from the fruits of Piper retrofractum. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates (1-32) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2. (E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide (9) showed a weak inhibitory effect, with an inhibition ratio of 52.0% at a concentration of 150 μM.

Keywords: Amides; Antiplatelet; Phenylpropanoids; Piper retrofractum; Piperaceae.