A Simultaneous Determination of Evodiamine and Rutaecarpine in Oriental Pharmaceutical Decoctions Containing Evodia Fruit by Ion-Pair High-Performance Liquid Chromatography

Ueda, Joji; Momma, Noriko; Yamauchi, Yasuhiko; Yoshie, Fumihiko; Ohsawa, Keisuke

doi:10.1248/yakushi1947.116.1_59

Cited by 9 publications

(10 citation statements)

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“…Inhibition of CYP3A4 by Evodia fruit extract: A methanol soluble fraction from Evodia fruit extract was preincubated with human liver microsomes in the presence of an NADPH-generating system (NADPHgs) (0.5 mM NADP ＋ , 5 mM MgCl2, 5 mM G-6-P and 1 UW mL G-6-P DH). The composition of the reaction mixture was 100 mM potassium phosphate (pH 7.4), 50 mM EDTA, 0.4 mg W mL human liver microsomal protein, 55 mg of dried Evodia fruit extract W mL and 100 mM [N-methyl- 14 The N-demethylation of erythromycin was determined by quantifying the amount of formaldehyde product as previously described. 6) Reactions were stopped by the addition of 10z (v W v) trichloroacetic acid (125 mL) after 10 min incubation at 379 C. Samples were then centrifuged at 1,600 g for 10 min at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Mechanism-Based Inactivation of Human Liver Microsomal CYP3A4 by Rutaecarpine and Limonin from Evodia Fruit Extract

Iwata

Tezuka

Kadota

et al. 2005

Drug Metabolism and Pharmacokinetics

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Evodia fruit (Evodiae Fructus) is used as a herbal medicine prepared from the matured fruit of the Evodia rutaecarpa Bentham or Evodia officinalis Dode, of the Rutaceae plant family. An extract of Evodia fruit in the presence of NADPH was shown to inhibit human liver microsomal erythromycin N-demethylation activity, mediated by cytochrome P450 3A4 (CYP3A4), in a preincubation-time dependent manner. The present study was conducted to identify components of Evodia fruit extract having preincubation-time dependent inhibitory effects on CYP3A4 by analyzing human liver microsomal erythromycin N-demethylation activity. Rutaecarpine, a major component of Evodia fruit, and limonin caused the most dramatic decrease in residual CYP3A4 activity (IC50 before and after 20 min preincubation with: rutaecarpine, >100 microM and 1.4 microM; limonin, 23.5 microM and 1.8 microM, respectively). Furthermore, rutaecarpine and limonin were identified as mechanism-based inhibitors of CYP3A4 from the following observations: 1) The inhibitory effects of rutaecarpine and limonin on CYP3A4 activity were dependent on the preincubation time, 2) The inhibition required NADPH, 3) The inhibition was depressed in the presence of the competitive CYP3A4 inhibitor, ketoconazole, 4) Dialysis resulted in no recovery of CYP3A4 activity. The kinetic parameters for inactivation k(inact) and K(I) were: 0.387 min-1 and 107.7 microM for rutaecarpine, 0.266 min-1 and 23.2 microM for limonin, respectively. These results indicate that rutaecarpine and limonin are mechanism-based inhibitors of CYP3A4.

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Section: Methodsmentioning

confidence: 99%

Mechanism-Based Inactivation of Human Liver Microsomal CYP3A4 by Rutaecarpine and Limonin from Evodia Fruit Extract

Iwata

Tezuka

Kadota

et al. 2005

Drug Metabolism and Pharmacokinetics

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“…In previous researches, TLC, HPLC with UV detector or MS as well as capillary electrophoresis (CE) were applied to quantitate or to identify these alkaloids in EF. [2526272829303132] To date, these developed methods have played very important roles in assessment on EF and EF-derived products. However, some of them either need quite long analysis time, or use complicated elution programs or mobile phases.…”

Section: Introductionmentioning

confidence: 99%

Development and validation of an UPLC-ESI-MS/MS method for determination of dehydroevodiamine, limonin, evodiamine, and rutaecarpine in Evodiae Fructus

Zhao

Zhou

et al. 2014

Phcog Mag

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Objective:Evodiae Fructus (EF), one of the most widely used traditional Chinese medicines, mainly consists of alkaloids, is widely used for the treatments of headache and gastrointestinal disorders. In this study, a sensitive and reliable UPLC-ESI-MS/MS method was developed for qualitative determination of dehydroevodiamine, limonin, evodiamine, and rutaecarpine.Materials and Methods:Chromatographic separations were accomplished on a Phenomenex Kinetex XB-C18 column (2.1 × 150 mm, 1.7 μm) by using a gradient elution profile with a mobile phase consisting of 0.5% formic acid in water (A) and acetonitrile (B). Detection was performed using multiple reactions monitoring mode under ESI in the positive ion mode.Results:The results showed good linearity over the investigated concentration ranges (R2>0.9900) for the analytes. The limit of quantitations (LOQs) were 6.88 ng/mL for dehydroevodiamine, 18.6 ng/mL for limonin, 6.24 ng/mL for evodiamine, and 2.56 ng/mL for rutaecarpine, respectively. Intraday and interday precisions (relative standard deviations, %) were <5% and accuracies ranged from 92% to 106%.Conclusion:The validated method was successfully applied to assay the contents of the four compounds in EF samples from different regions, with which just 10 min was needed to analyze each sample.

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“…HPLC and LC/MS/MS have been used for determination of rutaecarpine in biological fluids (Ueda et al, 1996;Ko et al, 2002;Lee et al, 2004). However, these published methods are generally tedious and time-consuming, or need mass spectrometer, which is expensive and not readily available in most clinical research laboratories.…”

Section: Measurement Of Rutaecarpine In Feces and Urine Samplementioning

confidence: 99%

“…Several high-performance liquid chromatography (HPLC) methods have been used to examine the concentration of rutaecarpine in plasma or in decoctions of Chinese medicine (Ko et al, 1994(Ko et al, , 2002Ueda et al, 1996). In addition, Ueda et al (1996) developed an ion-paired HPLC method to evaluate the contents of rutaecarpine in oriental pharmaceutical decoctions containing Evodia fruit.…”

Section: Introductionmentioning

confidence: 99%

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Elimination of rutaecarpine and its metabolites in rat feces and urine measured by liquid chromatography

Jan

Lin

Don

et al. 2006

Biomed. Chromatogr.

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Rutaecarpine is an alkaloid isolated from the medicinal herb Evodia rutaecarpa. This study was to evaluate the elimination pathway of rutaecarpine in rat feces and urine. Rutaecarpine and its metabolites (3-, 10-, 11- and 12-hydroxyrutaecarpine) in urine were measured after incubation with beta-glucuronidase. After the rutaecarpine was administered (25 and 100 mg/kg) orally to rats, the urine and fecal samples were collected using a metabolic cage for five consecutive days. For determining rutaecarpine, the mobile phase consisted of acetontrile-10 mM NaH(2)PO(4) (60:40, v/v, pH 4.2 adjusted with orthophosphoric acid) with a flow rate of 1 mL/min. The calibration curve was linear in concentrations of 0.05-50 microg/mL in fecal and urine sample. The results indicated that more than 42% of the rutaecarpine was excreted by feces after oral administration (25 and 100 mg/kg), but only a small amount of rutaecarpine was detected in urine at a higher dose of rutaecarpine (100 mg/kg). After incubation with beta-glucuronidase, the hydroxyrutaecarpine in urine was eluted using methanol-acetonitrile-0.04% formic acid (6:30:64, v/v) with a flow rate of 1.2 mL/min. We conclude that the metabolic pathway of rutaecarpine went through phase I hydroxylation and phase II conjugation, and the major metabolite is 10-hydroxyrutaecarpine eliminated from urine of the rat.

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A Simultaneous Determination of Evodiamine and Rutaecarpine in Oriental Pharmaceutical Decoctions Containing Evodia Fruit by Ion-Pair High-Performance Liquid Chromatography

Cited by 9 publications

References 0 publications

Mechanism-Based Inactivation of Human Liver Microsomal CYP3A4 by Rutaecarpine and Limonin from Evodia Fruit Extract

Mechanism-Based Inactivation of Human Liver Microsomal CYP3A4 by Rutaecarpine and Limonin from Evodia Fruit Extract

Development and validation of an UPLC-ESI-MS/MS method for determination of dehydroevodiamine, limonin, evodiamine, and rutaecarpine in Evodiae Fructus

Elimination of rutaecarpine and its metabolites in rat feces and urine measured by liquid chromatography

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