Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatography–tandem mass spectrometry for pharmacokinetic studies

Gu, Ruixia; Dou, Guifang; Wang, Jing; Dong, Jun-Xing; Zhang, Meng

doi:10.1016/j.jchromb.2006.12.055

Cited by 26 publications

(19 citation statements)

References 21 publications

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“…The physiological effects of caffeoylquinic acid derivatives with multiple caffeoyl groups are generally greater than those of monocaffeoylquinic acids, perhaps because the antioxidant activity is largely determined by the number of hydroxyl groups present on the aromatic rings (Wang et al, 2003;Islam, 2006). Furthermore, both diCQAs and triCQAs may function as inhibitors of the activity of HIV integrase, which catalyzes the insertion of viral DNA into the genome of host cells (McDougall et al, 1998;Slanina et al, 2001;Gu et al, 2007).…”

mentioning

confidence: 99%

Dual Catalytic Activity of Hydroxycinnamoyl-Coenzyme A Quinate Transferase from Tomato Allows It to Moonlight in the Synthesis of Both Mono- and Dicaffeoylquinic Acids

et al. 2014

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Tomato (Solanum lycopersicum), like other Solanaceous species, accumulates high levels of antioxidant caffeoylquinic acids, which are strong bioactive molecules and protect plants against biotic and abiotic stresses. Among these compounds, the monocaffeoylquinic acids (e.g. chlorogenic acid [CGA]) and the dicaffeoylquinic acids (diCQAs) have been found to possess marked antioxidative properties. Thus, they are of therapeutic interest both as phytonutrients in foods and as pharmaceuticals. Strategies to increase diCQA content in plants have been hampered by the modest understanding of their biosynthesis and whether the same pathway exists in different plant species. Incubation of CGA with crude extracts of tomato fruits led to the formation of two new products, which were identified by liquid chromatography-mass spectrometry as diCQAs. This chlorogenate:chlorogenate transferase activity was partially purified from ripe fruit. The final protein fraction resulted in 388-fold enrichment of activity and was subjected to trypsin digestion and mass spectrometric sequencing: a hydroxycinnamoyl-Coenzyme A:quinate hydroxycinnamoyl transferase (HQT) was selected as a candidate protein. Assay of recombinant HQT protein expressed in Escherichia coli confirmed its ability to synthesize diCQAs in vitro. This second activity (chlorogenate:chlorogenate transferase) of HQT had a low pH optimum and a high K m for its substrate, CGA. High concentrations of CGA and relatively low pH occur in the vacuoles of plant cells. Transient assays demonstrated that tomato HQT localizes to the vacuole as well as to the cytoplasm of plant cells, supporting the idea that in this species, the enzyme catalyzes different reactions in two subcellular compartments.

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confidence: 99%

Dual Catalytic Activity of Hydroxycinnamoyl-Coenzyme A Quinate Transferase from Tomato Allows It to Moonlight in the Synthesis of Both Mono- and Dicaffeoylquinic Acids

et al. 2014

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“…In addition, an internal standard method was used for quantitative analysis successfully with high precision and accuracy. All above described are advantages over the previously reported methods (Gu et al, 2007). This method was validated for its selectivity, accuracy, precision and sensitivity, and was successfully applied to a phase II clinical pharmacokinetic study of 1,5-DCQA.…”

Section: Resultsmentioning

confidence: 97%

“…A LC-MS/MS method for simultaneous determination of 1,5-DCQA, 1,5-CFQA and 1,5-DFQA in human plasma has been described in previous report (Gu et al, 2007). The quantitative analysis was accomplished using an external standard method.…”

Section: Development Of Methodsmentioning

confidence: 99%

“…Yang et al (2005) described a HPLC assay with UV detection to determine the 1,5-DCQA levels in rat plasma, with a lower limit of quantifi cation (LLOQ) of 15 ng/mL. Gu et al (2007) developed a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for simultaneous determination of 1,5-DCQA and its active metabolites in human plasma, using an external standard method as quantitative analysis, with an LLOQ of 3 ng/mL for each analyte.…”

Section: Introductionmentioning

confidence: 99%

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An improved LC‐MS/MS method for simultaneous determination of 1,5‐dicaffeoylquinic acid and its active metabolites in human plasma and its application to a pharmacokinetic study in patients

Liu

Dou²,

Dong

et al. 2010

Biomedical Chromatography

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In this study, a sensitive, selective and reproducible liquid chromatography-tandem mass spectrometry method for the simultaneous determination of 1,5-dicaffeoylquinic acid (1,5-DCQA) and its active metabolites, 1-caffeoyl-5-feruoylquinic acid and 1,5-O-diferuoylquinic acid, in human plasma, using puerarin as internal standard, was developed and validated. Analytes were extracted from plasma samples by liquid-liquid extraction with ethyl acetate, separated on a C(18) reversed-phase column with water containing 5 mM ammonium acetate and acetonitrile as the mobile phase and detected by electrospray ionization mass spectrometry in negative selected reaction monitoring mode. The accuracy and precision of the method were acceptable and linearity was good over the range 1-200 ng/mL for each analyte. In addition, the selectivity, extraction recovery and matrix effect were satisfactory too. The validated LC-MS/MS method was successfully applied to phase II clinical pharmacokinetic study of 1,5-DCQA in patients.

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“…Chlorogenic acids belongs to a large family of esters condensed by quinic acid (such as shikimic acid, queenie methyl or butyl 4-deoxy-quinic acid ) and trans-cinnamic acids (such caffeic, ferulic, p-coumaric, sinapic and dimethoxycinnamic acid) ( Robinson et al, 1996;Lai et al, 2007;Gu et al, 2007). In IUPAC system (-)-quinic acid is defined as 1L-1(OH), 3,4/5-tetrahydroxy-cyclohexane carboxylic acid and this same nomenclature is used throughout this paper (Han et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Identification and purification of novel chlorogenic acids in Artemisia annua L.

Zhao¹,

Zhang²,

Chen³

et al. 2015

JEBAS

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Present work has been carried out to study the identification and purification of chlorogenic acids in Artemisia annua L. Thirty-six chlorogenic acids were identified from this plant. Among these fifteen viz. two monocaffeoylquinic acids (Mr354), five dicaffeoylquinic acids (Mr516), one feruloylquinic acid (Mr368), three caffeoylferuloylquinic acids (Mr530), two ferulylquinic acids (Mr544), one dimethoxy-cinnamoylquinic acid (Mr382) and one p-coumaroylquinic acid (Mr338) were reported first time in present study by LC/MS n . Cis-isomers of these chlorogenic acids were also identified.Furthermore, column chromatography was used for the separation and purification of these chlorogenic acid; by the use of petroleum ether and ethyl acetate decolorization methods as mentioned in the literature, thus separation and purification process carried out at the same time. Polyamide and dextran were also used to purify Dicaffeoylquinic acid and purity level reached 85.7% with a yield of 53.4% after the secondary purification by Sephadex LH-20. Result of study revealed that A. annua can not only used for the production of artemisinin, but also yielding different kinds of chlorogenic acids, thus making comprehensive utilization of this plant.

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Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatography–tandem mass spectrometry for pharmacokinetic studies

Cited by 26 publications

References 21 publications

Dual Catalytic Activity of Hydroxycinnamoyl-Coenzyme A Quinate Transferase from Tomato Allows It to Moonlight in the Synthesis of Both Mono- and Dicaffeoylquinic Acids

Dual Catalytic Activity of Hydroxycinnamoyl-Coenzyme A Quinate Transferase from Tomato Allows It to Moonlight in the Synthesis of Both Mono- and Dicaffeoylquinic Acids

An improved LC‐MS/MS method for simultaneous determination of 1,5‐dicaffeoylquinic acid and its active metabolites in human plasma and its application to a pharmacokinetic study in patients

Identification and purification of novel chlorogenic acids in Artemisia annua L.

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