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

Alexander J Yoon; Haiqiang Wu; Roy D Pan; Bruce Teter; Jack Cipolla; Edwin Chang; Luis Z Avila; Saroj K Basak; Eri S Srivatsan; Marilene B Wang; Greg M Cole; Sally A Frautschy; Phillip D Hampton; Kym F Faull

doi:10.1016/j.ab.2020.113636

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

Anal Biochem. 2020 May 1:596:113636. doi: 10.1016/j.ab.2020.113636. Epub 2020 Feb 17.

Authors

Alexander J Yoon¹, Haiqiang Wu², Roy D Pan³, Bruce Teter⁴, Jack Cipolla⁵, Edwin Chang⁶, Luis Z Avila⁷, Saroj K Basak⁸, Eri S Srivatsan⁹, Marilene B Wang¹⁰, Greg M Cole⁴, Sally A Frautschy⁴, Phillip D Hampton¹¹, Kym F Faull⁵

Affiliations

¹ 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. Electronic address: [email protected].
² 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; School of Pharmaceutical Sciences, Health Science Center, Shenzhen University, Shenzhen 518060, China.
³ Department of Chemistry & Biochemistry, University of California Los Angeles, Los Angeles, CA 90095, USA; Department of Molecular & Medical Pharmacology, University of California Los Angeles, Los Angeles, CA, 90095, USA.
⁴ Department of Neurology, David Geffen School of Medicine, University of California Los Angeles, Los Angeles, CA 90095, USA.
⁵ 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.
⁶ Department of Radiology, Stanford University, Stanford, CA 94305, USA.
⁷ Aveta Biomics, Bedford, MA, 01730, USA.
⁸ Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA; Department of Surgery, David Geffen School of Medicine at UCLA, Los Angeles, CA 90073, USA; Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA.
⁹ Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA; Department of Surgery, David Geffen School of Medicine at UCLA, Los Angeles, CA 90073, USA; Department of Surgery, Veterans Administration Greater Los Angeles Health System, Los Angeles, CA 90073, USA; Department of Head & Neck Surgery, David Geffen School of Medicine at UCLA, Los Angeles, CA 90073, USA.
¹⁰ Department of Head & Neck Surgery, David Geffen School of Medicine at UCLA, Los Angeles, CA 90073, USA; Department of Chemistry, California State University Channel Islands, Camarillo, CA 93012, USA.
¹¹ Department of Chemistry, California State University Channel Islands, Camarillo, CA 93012, USA.

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.

Keywords: Boron trifluoride (BF(3)); Curcumin; Curcuminoids; Liquid chromatography coupled mass spectrometry (LCMS); Pharmacokinetics.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Animals
Boranes / chemistry*
Chromatography, Liquid
Diarylheptanoids / blood*
Diarylheptanoids / chemistry
Diarylheptanoids / isolation & purification
Healthy Volunteers
Humans
Mass Spectrometry
Mice
Molecular Structure

Substances

Boranes
Diarylheptanoids
boron trifluoride

Abstract

Publication types

MeSH terms

Substances

Grants and funding