Characterization of a new rat urinary metabolite of piperine by LC/NMR/MS studies.
Potential of piperine, an active alkaloid of black and long peppers, to increase the bioavailability of drugs in humans is of great clinical significance owing to its omnipresence in food. In an attempt to further study the reported differences in its metabolism in rats and humans, a new major urinary metabolite was detected in rat urine and plasma using HPLC. The metabolite was partially purified using reverse phase column chromatography on Sephadex((R))-LH 20 and characterized as 5-(3, 4-methylenedioxy phenyl)-2E,4E-pentadienoic acid-N-(3-yl propionic acid)-amide with the help of LC/NMR/positive ESI-MS studies. Complete mass fragmentation pattern could be assigned with MS/MS studies. The metabolite has a unique structure compared to the previously reported metabolites in that it retains methylenedioxy ring and conjugated double bonds while the piperidine ring is modified to form propionic acid group. Mechanism of formation of the metabolite by oxidation and cleavage of piperidine ring is proposed. Kidney appears to be the major excretion route for piperine metabolites in rats as no metabolite could be detected in feces.
Bajad
Sunil
S
Pharmacology Division, Regional Research Laboratory, Canal Road, Jammu, 180 001, India. sbajad@yahoo.com
Coumar
Mohane
M
Khajuria
Ravi
R
Suri
Om P
OP
Bedi
Kasturi L
KL
D000470:Alkaloids; D000818:Animals; D052117:Benzodioxoles; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D005243:Feces / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D010880:Piperidines / Q000097:blood / Q000652:urine*; D053284:Polyunsaturated Alkamides; D051381:Rats; D017208:Rats, Wistar; D013056:Spectrophotometry, Ultraviolet
D000470:Alkaloids; D052117:Benzodioxoles; D010880:Piperidines; D053284:Polyunsaturated Alkamides; C008922:piperine