2017
DOI: 10.1016/j.phytochem.2016.12.016
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Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells

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Cited by 14 publications
(15 citation statements)
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“…trans- pellitorine is lacking the vanillyl-group, but shares the amide group coupled to a carbon chain with the TRPV1 agonists capsaicin and nonivamide. The alkamide trans- pellitorine present in Piper and Macropiper species is known for its tingling effects (Obst et al, 2017), which is why the aroma compound has been discussed as a TRPV1 and also TRPA1 agonist as well (Sharma et al, 2011; Boonen et al, 2012). However, a recent study from our own group showed that trans- pellitorine does not directly activate TRPV1 and TRPA1, although both TRP channels seemed to be involved in the signaling cascade of the anti-inflammatory activity of trans- pellitorine in U937 macrophages (Walker et al, 2017).…”
Section: Discussionmentioning
confidence: 99%
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“…trans- pellitorine is lacking the vanillyl-group, but shares the amide group coupled to a carbon chain with the TRPV1 agonists capsaicin and nonivamide. The alkamide trans- pellitorine present in Piper and Macropiper species is known for its tingling effects (Obst et al, 2017), which is why the aroma compound has been discussed as a TRPV1 and also TRPA1 agonist as well (Sharma et al, 2011; Boonen et al, 2012). However, a recent study from our own group showed that trans- pellitorine does not directly activate TRPV1 and TRPA1, although both TRP channels seemed to be involved in the signaling cascade of the anti-inflammatory activity of trans- pellitorine in U937 macrophages (Walker et al, 2017).…”
Section: Discussionmentioning
confidence: 99%
“…As an alkamide, trans- pellitorine [(2 E ,4 E )-decadienoic acid N -isobutyl amide] shares some structural motifs with the capsaicinoids capsaicin and nonivamide, but is lacking the vanillyl-goup. trans- pellitorine is sensorially not described as pungent but induces a tingling effect in the oral cavity (Obst et al, 2017). This is congruent with a recent study from our own group which demonstrates that trans- pellitorine is not directly activating TRPV1 (Walker et al, 2017).…”
Section: Introductionmentioning
confidence: 99%
“…Tran and collaborators [13] mentioned that the flavour threshold for ethanol is around 1-2; therefore, it is likely that the panellists were describing another flavour that is similar to ethanol, as the Kawakawa contained only 0.4% alcohol, though it may have played a slight role in the bitter flavour described. Many of the flavour and mouthfeel characteristics could be explained by the presence of compounds such as piperidides, isobutyl amides, and esters [23]. Furthermore, compounds of essential oils such as myristicin might contribute to the strong aroma and flavour found in the Kawakawa Kombucha.…”
Section: Descriptive Analysis Of Samples By Focus Groupmentioning
confidence: 99%
“…The known compounds (+)-phenylalanine betaine ( 10 ) [ 19 ], (-)-mangochinine ( 11 ) [ 20 ], xylopinidine ( 12 ) [ 21 ], (-)-oblongine ( 13 ) [ 22 ], pellitorine ( 14 ) [ 23 ], (2 E ,4 E )- N -isobutyl-2,4-dodecadienamide ( 15 ) [ 24 ], retrofractamide A ( 16 ) [ 23 ], guineensine ( 17 ) [ 23 ], brachystamide B ( 18 ) [ 25 ], retrofractamide C ( 19 ) [ 26 ], sarmentine ( 20 ) [ 27 ], 3-(3,4-dimethoxyphenyl)propanoylpyrrole ( 21 ) [ 28 ], N - trans -feruloyltyramine ( 22 ) [ 29 ], (-)-machilusin ( 23 ) [ 30 ], galgravin ( 24 ) [ 31 ], (-)-nectandrin A ( 25 ) [ 32 ], methyl 3-(3,4-dimethoxyphenyl)propanoate ( 26 ) [ 33 ], piperic acid ( 27 ) [ 34 ], methyl piperate ( 28 ) [ 34 ], methyl (2 E ,4 E )-7-(1,3-benzodioxol-5-yl)hepta-2,4-dienoate ( 29 ) [ 35 ], (-)-blumenol B ( 30 ) [ 36 ], (-)-T-muurolol ( 31 ) [ 37 ], trans -phytol ( 32 ) [ 38 ], α-tocopherolquinone ( 33 ) [ 39 ], γ-tocopherol ( 34 ) [ 40 ], stigmast-4-ene-3,6-dione ( 35 ) [ 41 ], (22 E )-stigmasta-4,22-diene-3,6-dione ( 36 ) [ 42 ], and (22 E )-stigmasta-4,6,8(14),22-tetraen-3-one ( 37 ) [ 43 ] were determined by comparing the NMR data of 10 – 37 and the optical rotation values of 10 – 13 , 23 – 25 , 30 , and 31 with those reported in the literature.…”
Section: Resultsmentioning
confidence: 99%