Quantitative analyses of indoloquinazoline alkaloids in Fructus Evodiae by high-performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry.

Fructus Evodiae (Wuzhuyu), the fruits of Evodia rutaecarpa and related varieties, is widely used in traditional Chinese medicine. The bioactive constituents include the indoloquinazoline alkaloids rutaecarpine, evodiamine and dehydroevodiamine. A new assay based on high-performance liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry (HPLC/UV/APCI-MS/MS) was developed for the measurement of the indoloquinazoline alkaloids in commercial Fructus Evodiae products. Initially, the MS/MS fragmentation pathways of indoloquinazoline alkaloids were investigated to identify fragment ions that might be useful for the sensitive and selective detection of trace indoloquinazoline alkaloids during LC/MS/MS. Then, quantitative MS analysis of five indoloquinazoline alkaloids in 12 commercial Fructus Evodiae products from different geographical sources was performed. Analyte recovery was in the range of 97.5-105.3% for all with relative standard deviations (RSDs) below 6%, the intra-assay and inter-assay RSDs were less than 7%, and good linear relationships were shown with correlation coefficients for the analytes exceeding 0.999. Therefore, this LC/MS/MS assay facilitated the rapid quantitative analysis of rutaecarpine, evodiamine, evodiamide, 14-formyldihydrorutaecarpine and dehydroevodiamine in 12 commercial Fructus Evodiae products with excellent recovery, repeatability, accuracy and sensitivity. This method is simple and specific and can be used for identification and quality control of this traditional Chinese remedy.

[1]  R. Bauer,et al.  Quinolone alkaloids from Evodia rutaecarpa: a potent new group of antimycobacterial compounds. , 2005, International journal of antimicrobial agents.

[2]  L. Kong,et al.  Preparative isolation and purification of alkaloids from the Chinese medicinal herb Evodia rutaecarpa (Juss.) Benth by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[3]  C. Teng,et al.  Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo. , 2005, Carcinogenesis.

[4]  B. Aggarwal,et al.  Evodiamine Abolishes Constitutive and Inducible NF-κB Activation by Inhibiting IκBα Kinase Activation, Thereby Suppressing NF-κB-regulated Antiapoptotic and Metastatic Gene Expression, Up-regulating Apoptosis, and Inhibiting Invasion* , 2005, Journal of Biological Chemistry.

[5]  S. Yao,et al.  Simultaneous analysis of protoberberine, indolequinoline and quinolone alkaloids in coptis-evodia herb couple and the Chinese herbal preparations by high-performance liquid chromatography-electrospray mass spectrometry. , 2005, Talanta.

[6]  R. Bauer,et al.  Inhibition of Leukotriene Biosynthesis by Quinolone Alkaloids from the Fruits of Evodia rutaecarpa , 2004, Planta medica.

[7]  Qi-zhi Wang,et al.  [Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth]. , 2004, Yao xue xue bao = Acta pharmaceutica Sinica.

[8]  Lie-Chwen Lin,et al.  Inhibitory effects of evodiamine on the growth of human prostate cancer cell line LNCaP , 2004, International journal of cancer.

[9]  C. Teng,et al.  Induction of mitotic arrest and apoptosis by evodiamine in human leukemic T-lymphocytes. , 2004, Life sciences.

[10]  M. Ogasawara,et al.  Inhibition by evodiamine of hepatocyte growth factor-induced invasion and migration of tumor cells. , 2004, Biological & pharmaceutical bulletin.

[11]  Li‐jun Wu,et al.  Intracellular regulation of evodiamine-induced A375-S2 cell death. , 2003, Biological & pharmaceutical bulletin.

[12]  Chang-Ping Hu,et al.  The Depressor and Vasodilator Effects of Rutaecarpine are Mediated by Calcitonin Gene-Related Peptide , 2003, Planta medica.

[13]  T. Ikejima,et al.  Evodiamine, a constituent of Evodiae Fructus, induces anti‐proliferating effects in tumor cells , 2003, Cancer science.

[14]  M. Ogasawara,et al.  Screening of natural compounds for inhibitory activity on colon cancer cell migration. , 2001, Biological & pharmaceutical bulletin.

[15]  J. Sheu,et al.  Antithrombotic effect of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa, on platelet plug formation in in vivo experiments , 2000, British journal of haematology.

[16]  T. Moon,et al.  A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa , 1999, Inflammation Research.

[17]  J. Ahn,et al.  Anti-Helicobacter pylori activity of quinolone alkaloids from Evodiae fructus. , 1999, Biological & pharmaceutical bulletin.

[18]  S. Sheu,et al.  Contents of constituents in mature and immature fruits of evodia species. , 1999, Planta medica.

[19]  M. Iinuma,et al.  Antinociceptive and Anti-Inflammatory Activities of Limonin Isolated from the Fruits of Evodia rutaecarpa var. bodinieri , 1998, Planta medica.

[20]  M. Iinuma,et al.  Antinociceptive activities of 70% methanol extract of evodiae fructus (fruit of Evodia rutaecarpa var. bodinieri) and its alkaloidal components. , 1997, Biological & pharmaceutical bulletin.

[21]  Lloyd R. Snyder,et al.  Practical HPLC Method Development: Snyder/Practical , 1997 .

[22]  Yuan-Qing Tang,et al.  Quinolone Alkaloids from Evodia rutaecarpa , 1996 .

[23]  C. H. Park,et al.  Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. , 1996, Planta medica.

[24]  A. Shum,et al.  Mechanisms of vasorelaxant effect of dehydroevodiamine: a bioactive isoquinazolinocarboline alkaloid of plant origin. , 1996, Journal of cardiovascular pharmacology.

[25]  S. Sheu,et al.  Determination of the alkaloids in Evodiae Fructus by high-performance liquid chromatography , 1996 .

[26]  C. F. Chen,et al.  The mechanism of the vasodilator effect of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa. , 1994, European journal of pharmacology.

[27]  J. Miller,et al.  Statistics for Analytical Chemistry , 1993 .

[28]  M. Berhow,et al.  Thin-layer and high-performance liquid chromatographic analyses of limonoids and limonoid glucosides in Citrus seeds , 1993 .

[29]  Professor Dr. Weici Tang,et al.  Chinese Drugs of Plant Origin , 1992, Springer Berlin Heidelberg.

[30]  Weici Tang,et al.  Evodia rutaecarpa (Juss.) Benth. , 1992 .

[31]  J. Kuo,et al.  The hypotensive and negative chronotropic effects of dehydroevodiamine. , 1990, European journal of pharmacology.

[32]  T. Miyase,et al.  Limonoids and Quinolone Alkaloids from Evodia rutaecarpa BENTHAM , 1988 .

[33]  Lloyd R. Snyder,et al.  Practical HPLC method development , 1988 .

[34]  Y. Ohizumi,et al.  Isolation of evodiamine, a powerful cardiotonic principle, from Evodia rutaecarpa Bentham (Rutaceae). , 1986, Journal of pharmaceutical sciences.

[35]  C. L. King,et al.  Uterotonic effect of Evodia rutaecarpa alkaloids. , 1980, Journal of natural products.