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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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
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Abstract 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.
AbstractList 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.
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 MS 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.
ArticleNumber 113636
Author Hampton, Phillip D.
Faull, Kym F.
Avila, Luis Z.
Basak, Saroj K.
Cole, Greg M.
Cipolla, Jack
Pan, Roy D.
Chang, Edwin
Teter, Bruce
Yoon, Alexander J.
Srivatsan, Eri S.
Frautschy, Sally A.
Wang, Marilene B.
Wu, Haiqiang
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  givenname: Alexander J.
  surname: Yoon
  fullname: Yoon, Alexander J.
  email: yoon2887@g.ucla.edu
  organization: Pasarow Mass Spectrometry Laboratory, Jane and Terry Semel Institute for Neuroscience and Human Behavior and Department of Psychiatry & Biobehavioral Sciences, David Geffen School of Medicine at UCLA, Los Angeles, CA 90095, USA
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  givenname: Haiqiang
  surname: Wu
  fullname: Wu, Haiqiang
  organization: Pasarow Mass Spectrometry Laboratory, Jane and Terry Semel Institute for Neuroscience and Human Behavior and Department of Psychiatry & Biobehavioral Sciences, David Geffen School of Medicine at UCLA, Los Angeles, CA 90095, USA
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  givenname: Roy D.
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  organization: Department of Chemistry & Biochemistry, University of California Los Angeles, Los Angeles, CA 90095, USA
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  givenname: Bruce
  surname: Teter
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  organization: Department of Neurology, David Geffen School of Medicine, University of California Los Angeles, Los Angeles, CA 90095, USA
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  surname: Cipolla
  fullname: Cipolla, Jack
  organization: Pasarow Mass Spectrometry Laboratory, Jane and Terry Semel Institute for Neuroscience and Human Behavior and Department of Psychiatry & Biobehavioral Sciences, David Geffen School of Medicine at UCLA, Los Angeles, CA 90095, USA
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  surname: Chang
  fullname: Chang, Edwin
  organization: Department of Radiology, Stanford University, Stanford, CA 94305, USA
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  givenname: Luis Z.
  surname: Avila
  fullname: Avila, Luis Z.
  organization: Aveta Biomics, Bedford, MA, 01730, USA
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  givenname: Saroj K.
  surname: Basak
  fullname: Basak, Saroj K.
  organization: Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA
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  givenname: Eri S.
  surname: Srivatsan
  fullname: Srivatsan, Eri S.
  organization: Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA
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  givenname: Marilene B.
  surname: Wang
  fullname: Wang, Marilene B.
  organization: Department of Head & Neck Surgery, David Geffen School of Medicine at UCLA, Los Angeles, CA 90073, USA
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  givenname: Greg M.
  surname: Cole
  fullname: Cole, Greg M.
  organization: Department of Neurology, David Geffen School of Medicine, University of California Los Angeles, Los Angeles, CA 90095, USA
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  givenname: Sally A.
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  fullname: Frautschy, Sally A.
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  givenname: Phillip D.
  surname: Hampton
  fullname: Hampton, Phillip D.
  organization: Department of Chemistry, California State University Channel Islands, Camarillo, CA 93012, USA
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  givenname: Kym F.
  surname: Faull
  fullname: Faull, Kym F.
  organization: Pasarow Mass Spectrometry Laboratory, Jane and Terry Semel Institute for Neuroscience and Human Behavior and Department of Psychiatry & Biobehavioral Sciences, David Geffen School of Medicine at UCLA, Los Angeles, CA 90095, USA
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Keywords Curcumin
Liquid chromatography coupled mass spectrometry (LCMS)
Boron trifluoride (BF3)
Pharmacokinetics
Curcuminoids
Boron trifluoride (BF)
Language English
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Snippet A procedure is described to measure curcumin (C), demethoxycurcumin (DMC), bisdemethoxycurcumin (BDMC), tetrahydrocurcumim (TC) and their glucuronidated...
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SubjectTerms 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
Title A sensitive LC-MS assay using derivatization with boron trifluoride to quantify curcuminoids in biological samples
URI https://dx.doi.org/10.1016/j.ab.2020.113636
https://www.ncbi.nlm.nih.gov/pubmed/32081619
Volume 596
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