Sesartemin

Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells.[Pubmed:28065397]

Phytochemistry. 2017 Mar;135:181-190.

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 muM. Piperdardine showed the most pronounced effect, with glucose uptake increased by 83 +/- 18% at 100 muM 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.

An ethnopharmacological examination of Virola elongata bark: a South American arrow poison.[Pubmed:6097773]

J Ethnopharmacol. 1984 Oct;12(1):75-92.

The use of the resin of Virola elongata as an arrow poison was investigated. Aqueous and methanolic extracts of the dried bark were not observed to have toxic effects when administered intraperitoneally to mice. In an attempt to determine if the hallucinogenic indole alkaloid constituents of the bark, which form the basis for the alternate use of this material as a ceremonial snuff, could also be responsible for its use as an arrow poison, alkaloidal and non-alkaloidal extracts were compared with respect to their behavioral effects on mice. The non-alkaloidal extract was more effective in producing an observable alteration in behavior. This consisted of a marked reduction in spontaneous locomotor activity. The extract was fractionated and 13 of the major constituents assayed for their ability to reduce spontaneous locomotor activity. Most of this biological activity of the extract was attributable to the presence of the bis-tetrahydrofuran lignans, epi-Sesartemin, Sesartemin, epi-yangambin and yangambin. Each of these compounds was also observed to reduce isolation induced aggression when administered to mice.