Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells

Katja Obst (Corresponding author), Barbara Lieder, Katharina V. Reichelt, Michael Backes, Susanne Paetz, Katrin Geissler, Gerhard Krammer, Veronika Somoza, Jakob P. Ley, Karl-Heinz Engel

Publications: Contribution to journalArticlePeer Reviewed

Abstract

The phytochemical profile of Macropiper excelsum (G.Forst.) Miq. subsp. excelsum (Piperaceae), a shrub which is widespread in New Zealand, was investigated by LC-MS-guided isolation and characterization via HR-ESI-TOF-MS and NMR spectroscopy. The isolated compounds were sensorily evaluated to identify their contribution to the overall taste of the crude extract with sweet, bitter, herbal and trigeminal impressions. Besides the known non-volatile Macropiper compounds, the lignans (+)-diayangambin and (+)-excelsin, four further excelsin isomers, (+)-diasesartemin, (+)-sesartemin, (+)-episesartemin A and B were newly characterized. Moreover, piperine and a number of piperine analogues as well as trans-pellitorine and two homologues, kalecide and (2E,4E)-tetradecadienoic acid N-isobutyl amide were identified in M. excelsum, some of them for the first time. Methyl(2E,4E)-7-(1,3-benzodioxol-5-yl)hepta-2,4-dienoate was identified and characterized for the first time in nature. Sensory analysis of the pure amides indicated that they contributed to the known chemesthetic effects of Macropiper leaves and fruits. Since the pungent piperine has been shown to affect glucose and fatty acid metabolism in vivo in previous studies, piperine itself and four of the isolated compounds, piperdardine, chingchengenamide A, dihydropiperlonguminine, and methyl(2E,4E)-7-(1,3-benzodioxol-5-yl)hepta-2,4-dienoate, were investigated regarding their effects on glucose and fatty acid uptake by enterocyte-like Caco-2 cells, in concentrations ranging from 0.1 to 100 μM. Piperdardine showed the most pronounced effect, with glucose uptake increased by 83 ± 18% at 100 μM compared to non-treated control cells. An amide group seems to be advantageous for glucose uptake stimulation, but not necessarily for fatty acid uptake-stimulating effects of piperine-related compounds.

Original languageEnglish
Pages (from-to)181-190
Number of pages10
JournalPhytochemistry
Volume135
DOIs
Publication statusPublished - Mar 2017

Austrian Fields of Science 2012

  • 106002 Biochemistry
  • 106034 Phytochemistry
  • 106023 Molecular biology

Keywords

  • Macropiper excelsum
  • Piperaceae
  • Kawakawa
  • Caco-2
  • Glucose uptake
  • Fatty acid uptake
  • Lignans
  • Piperine analogues
  • Fatty acid alkamides
  • IN-VITRO
  • SEQUENCE DATA
  • LINE CACO-2
  • NEW-ZEALAND
  • LIGNANS
  • PIPERACEAE
  • CHEMISTRY
  • AMIDE
  • PIPERDARDINE
  • CONSTITUENTS

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