HPLC-MS/MS analysis of ilimaquinone and its application in a pharmacokinetic study in rats

Son, Heebin; Noh, Keumhan; Kang, Changhyun; Na, MinKyun; Oh, Sangtaek; Song, Im‐Sook; Kang, Wonku

doi:10.1016/j.jpba.2019.01.030

Cited by 11 publications

(9 citation statements)

References 11 publications

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“…Deprotonated shikimic acid ([M-H] − at m / z 173.4) was fragmented into its largest product ion at m / z 136.6, with a collision energy of −16 eV. The transition from the IS precursor to the [M-H] − product ion occurred at 296.1→251.7 (collision energy −18 eV), as reported previously [ 20 , 21 , 22 ].…”

Section: Resultssupporting

confidence: 62%

“…Although a synthetic method labeling shikimic acid with deuterium at positions C3 and C4 is available [ 23 ], it is impractical, as there are many steps and a low yield. Therefore, diclofenac served as a stable IS, as in many previous reports from our laboratory [ 20 , 21 , 22 ].…”

Section: Resultsmentioning

confidence: 94%

“…Instead, we tested solid-phase extraction using an anion exchange column, but the recovery rate was very low. We tested a simple precipitation procedure using a mixture of methanol and 10% ZnSO4 aqueous solution (4:1, v / v ) [ 18 ], trichloroacetic acid (5% w / v ) [ 19 ], methanol, and acetonitrile separately [ 20 , 21 , 22 ], but the sensitivity was poor. Therefore, the organic layer was evaporated after protein precipitation with five volumes of acetonitrile, and the plasma samples were finally concentrated twofold.…”

Section: Resultsmentioning

confidence: 99%

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Pharmacokinetics of Shikimic Acid Following Intragastric and Intravenous Administrations in Rats

et al. 2020

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Shikimic acid, a critical starting material for the semi-total synthesis of oseltamivir to treat and prevent influenza, exerts many pharmacological effects. However, the optimal bioanalytical method has not been adequately defined. We used liquid chromatography-tandem mass spectrometry to quantitate shikimic acid in rat plasma and studied its pharmacokinetics after intragastric and intravenous administration. Plasma was spiked with an internal standard, and the proteins were precipitated with acetonitrile, followed by solvent evaporation and reconstitution of the mobile phase. Shikimic acid was separated on a hydrophilic reverse-phase column and showed a mass transition ([M-H]−) at m/z 173.4→136.6. Shikimic acid exhibited bi-exponential decay after intravenous dosing, with a rapid distribution (5.57 h−1) up to 1 h followed by slow elimination (0.78 h−1). The steady state distribution and clearance volumes were 5.17 and 1.79 L/h/kg, respectively. After intragastric administration, the shikimic acid level peaked at about 3 h, and the material then disappeared mono-exponentially with a half-life of 1.3 h. A double peak phenomenon was observed. The absolute oral bioavailability was about 10% in rats. We explored the relationship between the pharmacokinetics and pharmacodynamics of shikimic acid.

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Section: Resultssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

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Pharmacokinetics of Shikimic Acid Following Intragastric and Intravenous Administrations in Rats

et al. 2020

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“…Reasonably, it is the pivotal approach to reveal the obscure pharmacodynamic properties and toxicity of herbals or formulas in TCM [156]. Commonly, LC-MS/MS [157], HPLC-MS/ MS [158], UPLC-MS/MS [159], and GC-MS [160] are the main techniques employed in PK investigation.…”

Section: Pharmacokinetic Investigationmentioning

confidence: 99%

Huang-Lian Jie-Du decoction: a review on phytochemical, pharmacological and pharmacokinetic investigations

Zhang

Zhu

2019

Chin Med

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Huang-Lian Jie-Du decoction (HLJDD), a famous traditional Chinese prescription constituted by Rhizoma Coptidis, Radix Scutellariae, Cortex Phellodendri and Fructus Gradeniae, has notable characteristics of dissipating heat and detoxification, interfering with tumors, hepatic diseases, metabolic disorders, inflammatory or allergic processes, cerebral diseases and microbial infections. Based on the wide clinical applications, accumulating investigations about HLJDD focused on several aspects: (1) chemical analysis to explore the underlying substrates responsible for the therapeutic effects; (2) further determination of pharmacological actions and the possible mechanisms of the whole prescription and of those representative ingredients to provide scientific evidence for traditional clinical applications and to demonstrate the intriguing molecular targets for specific pathological processes; (3) pharmacokinetic feature studies of single or all components of HLJDD to reveal the chemical basis and synergistic actions contributing to the pharmacological and clinically therapeutic effects. In this review, we summarized the main achievements of phytochemical, pharmacological and pharmacokinetic profiles of HLJDD and its herbal or pharmacologically active chemicals, as well as our understanding which further reveals the significance of HLJDD clinically.

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“…It was also used in a pharmacokinetic study following per oral (p.o.) administration of IQ [10]. Because IQ is unstable in rat plasma, ascorbic acid was added to the plasma during sample preparation to ensure the chemical stability of the quinone moiety of IQ [11].…”

Section: Introductionmentioning

confidence: 99%

Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted from a Marine Sponge in Rats

et al. 2019

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An ilimquinone (IQ) mixture isolated from Hippiospongia metachromia, consisting of IQ and epi-ilimaquinone (epi-IQ), exerts anti-HIV, anti-microbial, anti-inflammatory, and anti-cancer effects. An HPLC-MS/MS method was developed for simultaneous determination of the two epimers in rat plasma, separating them using a biphenyl column. Ascorbic acid is added during the sample preparation to ensure the stability of both isomers. The plasma concentrations of the isomers were monitored following intravenous and oral administration of the IQ mixture in rats as well as the individual epimers that were separately orally administered. Compare to IQ, epi-IQ was much more stable in rat plasma, likely due to its configurations of decalin. Both substances decayed in more than bi-exponential pattern, with an elimination rate constant of 1.2 h−1 for IQ and 1.7 h−1 for epi-IQ. The epi-IQ was distributed more widely than IQ by about two-fold. Consequently, the clearance of epi-IQ was greater than that of IQ by about three-fold. The oral absolute bioavailability for IQ was 38%, and, that for epi-IQ, was 13%. Although the systemic exposure of IQ was greater than that of epi-IQ by ~8.7-fold, the clearance of each isomer was similar when administered either orally or intravenously, when normalized for bioavailability. The stereo-specific behavior of the isomers appears to originate from differences in both their tissue distribution and gastrointestinal permeability.

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HPLC-MS/MS analysis of ilimaquinone and its application in a pharmacokinetic study in rats

Cited by 11 publications

References 11 publications

Pharmacokinetics of Shikimic Acid Following Intragastric and Intravenous Administrations in Rats

Pharmacokinetics of Shikimic Acid Following Intragastric and Intravenous Administrations in Rats

Huang-Lian Jie-Du decoction: a review on phytochemical, pharmacological and pharmacokinetic investigations

Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted from a Marine Sponge in Rats

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