TY - JOUR
T1 - LC-HRMS/MS-based phytochemical profiling of Piper spices
T2 - Global association of piperamides with endocannabinoid system modulation
AU - Luca, Simon Vlad
AU - Minceva, Mirjana
AU - Gertsch, Jürg
AU - Skalicka-Woźniak, Krystyna
N1 - Publisher Copyright:
© 2021 Elsevier Ltd
PY - 2021/3
Y1 - 2021/3
N2 - The plant genus Piper comprises extensively consumed spice taxa like black pepper (P. nigrum L.) or long pepper (P. longum L.). The chronic dietary use of different Piper spices has been associated with different health benefits, though the molecular mechanisms remain poorly understood. The aim of this work was to perform the liquid-chromatography-high-resolution tandem mass spectrometry (LC-HRMS/MS) profiling and LC-DAD quantification of piperamides in several Piper species and varieties and study their ability to modulate the endocannabinoid system (ECS). LC-HRMS/MS analysis revealed a number of 42 piperamides grouped into six structural classes, with 22 of them, notably piperine, retrofractamide B, guineensine, piperchabamide C, being also quantified by LC-DAD. The multivariate analysis showed that P. nigrum and P. longum are very similar with respect to their piperamide profile, while the other Piper spices (P. retrofractum, P. guineense, P. cubeba, P. borbonense) might have significantly different metabolite patterns. The results from the biological assays confirmed that guineensine and total piperamides are strongly correlated with anandamide (AEA) cellular uptake inhibition. While none of the Piper spice extracts showed binding activity at cannabinoid CB1 receptors, some P. nigrum varieties exhibited moderate binding interactions with CB2 receptors. Overall, the analytical profiling enabled global annotations of piperamides associated to cannabimimetic effects in Piper spices.
AB - The plant genus Piper comprises extensively consumed spice taxa like black pepper (P. nigrum L.) or long pepper (P. longum L.). The chronic dietary use of different Piper spices has been associated with different health benefits, though the molecular mechanisms remain poorly understood. The aim of this work was to perform the liquid-chromatography-high-resolution tandem mass spectrometry (LC-HRMS/MS) profiling and LC-DAD quantification of piperamides in several Piper species and varieties and study their ability to modulate the endocannabinoid system (ECS). LC-HRMS/MS analysis revealed a number of 42 piperamides grouped into six structural classes, with 22 of them, notably piperine, retrofractamide B, guineensine, piperchabamide C, being also quantified by LC-DAD. The multivariate analysis showed that P. nigrum and P. longum are very similar with respect to their piperamide profile, while the other Piper spices (P. retrofractum, P. guineense, P. cubeba, P. borbonense) might have significantly different metabolite patterns. The results from the biological assays confirmed that guineensine and total piperamides are strongly correlated with anandamide (AEA) cellular uptake inhibition. While none of the Piper spice extracts showed binding activity at cannabinoid CB1 receptors, some P. nigrum varieties exhibited moderate binding interactions with CB2 receptors. Overall, the analytical profiling enabled global annotations of piperamides associated to cannabimimetic effects in Piper spices.
KW - Endocannabinoid system
KW - Guineensine
KW - LC-HRMS/MS
KW - Piper spp.
KW - Piperamides
KW - Spices
UR - http://www.scopus.com/inward/record.url?scp=85099777799&partnerID=8YFLogxK
U2 - 10.1016/j.foodres.2021.110123
DO - 10.1016/j.foodres.2021.110123
M3 - Article
C2 - 33641990
AN - SCOPUS:85099777799
SN - 0963-9969
VL - 141
JO - Food Research International
JF - Food Research International
M1 - 110123
ER -