A sensitive LC-MS assay using derivatization with boron trifluoride to quantify curcuminoids in biological samples

A sensitive LC-MS assay using derivatization with boron trifluoride to quantify curcuminoids in biological samples

A procedure is described to measure curcumin (C), demethoxycurcumin (DMC), bisdemethoxycurcumin (BDMC), tetrahydrocurcumim (TC) and their glucuronidated metabolites (CG, DMCG, and BDMCG) in plasma, brain, liver and tumor samples. The procedure involves converting the analytes to their boron difluori...

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Bibliographic Details
Published in:Analytical biochemistry Vol. 596; p. 113636
Main Authors: Yoon, Alexander J., Wu, Haiqiang, Pan, Roy D., Teter, Bruce, Cipolla, Jack, Chang, Edwin, Avila, Luis Z., Basak, Saroj K., Srivatsan, Eri S., Wang, Marilene B., Cole, Greg M., Frautschy, Sally A., Hampton, Phillip D., Faull, Kym F.
Format: Journal Article
Language:English
Published: United States Elsevier Inc 01-05-2020
Subjects:
Animals
Boranes - chemistry
Boron trifluoride (BF3)
Chromatography, Liquid
Curcumin
Curcuminoids
Diarylheptanoids - blood
Diarylheptanoids - chemistry
Diarylheptanoids - isolation & purification
Healthy Volunteers
Humans
Liquid chromatography coupled mass spectrometry (LCMS)
Mass Spectrometry
Mice
Molecular Structure
Pharmacokinetics
Curcumin
Liquid chromatography coupled mass spectrometry (LCMS)
Boron trifluoride (BF3)
Pharmacokinetics
Curcuminoids
Boron trifluoride (BF)
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Description
Summary:A procedure is described to measure curcumin (C), demethoxycurcumin (DMC), bisdemethoxycurcumin (BDMC), tetrahydrocurcumim (TC) and their glucuronidated metabolites (CG, DMCG, and BDMCG) in plasma, brain, liver and tumor samples. The procedure involves converting the analytes to their boron difluoride derivatives and analyzing them by combined liquid chromatography coupled to an ion trap mass spectrometer operating in the negative ion MSn scan mode. The method has superb limits of detection of 0.01 nM for all curcuminoids and 0.5 nM for TC and the glucuroniated metabolites, and several representative chromatograms of biological samples containing these analytes are provided. In addition, the pharmacokinetic profile of these compounds in one human who daily consumed an over-the-counter curcuminoid product shows the peak and changes in circulating concentrations achieved by this mode of administration. [Display omitted] •Conversion of curcuminoids into BF2-curcuminoid complexes can be achieved in a simple one-step reaction, optimized for LC-MS analysis.•BF2-curcuminoid complexes yield an average of 28 fold increase in sensitivity on the negative ESI analysis.•The improved sensitivity of the assay enabled quantitation of these compounds in small amounts of soft tissues.•We demonstrate the application of our assay by analyzing human plasma and various soft tissues from mice.
ISSN:0003-2697
1096-0309
DOI:10.1016/j.ab.2020.113636