A high-throughput quantification method of curcuminoids and curcumin metabolites in human plasma via high-performance liquid chromatography/tandem mass spectrometry

Abstract

Curcuminoids, a mixture of curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC), have shown a variety of clinical benefits for several human chronic diseases including osteoarthritis, rheumatoarthritis, and type II diabetes. However, the oral bioavailability of curcumin is extremely low due to its avid metabolism to curcumin O-glucuronide (COG), curcumin O-sulfate (COS), tetrahydrocurcumin (THC), and other minor metabolites. This paper reports a unique liquid chromatography/tandem mass spectrometry (LC-MS/MS) method to quantify curcumin, DMC, BDMC, COG, COS, and THC simultaneously in human plasma. These compounds were extracted with ethyl acetate from human plasma, separated on a BetaBasic-8 column, and monitored on a triple quadruple mass spectrometer coupled with API electrospray under a negative ion mode. The linearity of these respective curcuminoids and curcumin metabolites was shown in the range of 2–1000 ng/mL with 85–115% accuracy and ≤20% precision in human plasma. This method was validated according to the US FDA GLP analytic criteria and applied to characterize the pharmacokinetics of curcumin, COG, and COS in human plasma after an oral dose of bioavailable curcumin (nanoemulsion curcumin).

Superior anticancer activity is demonstrated by total extract of Curcuma longa L. as opposed to individual curcuminoids separated by centrifugal partition chromatography

“…Positive ionization mode delivered different fragmentation patterns: for curcumin, the listed m/z signals were recorded: 391, 369, 285, 253, 177, 161, 145, and 117; for DMCC: 361, 339, 255, 223, 177, 147, 145, 131, and 117; and for BDMCC: 331, 309, 225, 189, 147, 131, and 117. The general fragmentation patterns of curcuminoids obtained in this study were in agreement with those previously reported by Cao, Xu, and Liu () and Jiang Soogyi, Jacobsen, Timmermann, and Gang (). However, the MS/MS spectra recorded by the authors using the Q‐TOF analyser revealed the presence of a higher number of fragments, which helped in the identification of these compounds.…”

Chemical profiling and quantification of Gua-Lou-Gui-Zhi decoction by high performance liquid chromatography/quadrupole-time-of-flight mass spectrometry and ultra-performance liquid chromatography/triple quadrupole mass spectrometry

“…These compounds had one carbonyl connected with a methylene (O C-CH 2 -) in their structures. Their characteristic fragmentation behaviors often took place in ˛ or ˇ-position of carbonyl group [40] (take 6-gingerol as an example, Fig. 3J).…”

Effectiveness of curcuminoids in the treatment of knee osteoarthritis: a systematic review and meta‐analysis of randomized clinical trials

“…8 Biochemically, the curcuminoids comprise curcumin, demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC), 9 and in soluble form generally exist as keto-enol tautomers. 10 Pharmacologically, curcuminoids have been reported to possess significant anti-inflammatory properties.…”