Metabolic profiling of the Uncaria Hook alkaloid geissoschizine methyl ether in rat and human liver microsomes using high-performance liquid chromatography with tandem mass spectrometry

Molecules

Volumn 20, Issue 2, 2015, Pages 2100-2114

  Kushida, Hirotaka ^a   Matsumoto, Takashi ^a   Igarashi, Yasushi ^a   Nishimura, Hiroaki ^a   Watanabe, Junko ^a   Maemura, Kazuya ^a   Kase, Yoshio ^a  

^a TSUMURA AND CO   (Japan)

Author keywords

Geissoschizine methyl ether; Human liver microsome; LC MS MS; Metabolic profile; Rat liver microsome; Uncaria hook

Indexed keywords

GEISSOSCHIZINE METHYLETHER; INDOLE ALKALOID; PLANT EXTRACT; TRANQUILIZER;

ANIMAL; BIOTRANSFORMATION; CHEMISTRY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROGENATION; LIVER MICROSOME; MALE; METABOLISM; METHYLATION; OXIDATION REDUCTION REACTION; SPRAGUE DAWLEY RAT; TANDEM MASS SPECTROMETRY; UNCARIA;

ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; HUMANS; HYDROGENATION; INDOLE ALKALOIDS; MALE; METHYLATION; MICROSOMES, LIVER; OXIDATION-REDUCTION; PLANT EXTRACTS; RATS, SPRAGUE-DAWLEY; TANDEM MASS SPECTROMETRY; TRANQUILIZING AGENTS; UNCARIA;

EID: 84921922908     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20022100     Document Type: Article

References (14)

1. Pengsuparp, T.; Indra, B.; Nakagawasai, O.; Tadano, T.; Mimaki, Y.; Sashida, Y.; Ohizumi, Y.; Kisara, K. Pharmacological studies of geissoschizine methyl ether, isolated from Uncaria sinensis Oliv., in the central nervous system. Eur. J. Pharmacol. 2001, 425, 211-218.
2. Kawakami, Z.; Kanno, H.; Ikarashi, Y.; Kase, Y. Yokukansan, a kampo medicine, protects against glutamate cytotoxicity due to oxidative stress in PC12 cells. J. Ethnopharmacol. 2011, 134, 74-81.
3. Imamura, S.; Tabuchi, M.; Kushida, H.; Nishi, A.; Kanno, H.; Yamaguchi, T.; Sekiguchi, K.; Ikarashi, Y.; Kase, Y. The blood-brain barrier permeability of geissoschizine methyl ether in Uncaria hook, a galenical constituent of the traditional Japanese medicine yokukansan. Cell. Mol. Neurobiol. 2011, 31, 787-793.
4. Nishi, A.; Yamaguchi, T.; Sekiguchi, K.; Imamura, S.; Tabuchi, M.; Kanno, H.; Nakai, Y.; Hashimoto, K.; Ikarashi, Y.; Kase, Y. Geissoschizine methyl ether, an alkaloid in Uncaria hook, is a potent serotonin (1A) receptor agonist and candidate for amelioration of aggressiveness and sociality by yokukansan. Neuroscience 2012, 207, 124-136.
5. Ueki, T.; Nishi, A.; Imamura, S.; Kanno, H.; Mizoguchi, K.; Sekiguchi, K.; Ikarashi, Y.; Kase, Y. Effects of geissoschizine methyl ether, an indole alkaloid in Uncaria hook, a constituent of yokukansan, on human recombinant serotonin 7 receptor. Cell. Mol. Neurobiol. 2013, 33, 129-135.
6. Ueda, T.; Ugawa, S.; Ishida, Y.; Shimada, S. Geissoschizine methyl ether has third-generation antipsychotic-like actions at the dopamine and serotonin receptors. Eur. J. Pharmacol. 2011, 671, 79-86.
7. Kushida, H.; Fukutake, M.; Tabuchi, M.; Katsuhara, T.; Nishimura, H.; Ikarashi, Y.; Kanitani, M.; Kase, Y. Simultaneous quantitative analyses of indole and oxindole alkaloids of Uncaria Hook in rat plasma and brain after oral administration of the traditional Japanese medicine yokukansan using high-performance liquid chromatography with tandem mass spectrometry. Biomed. Chromatogr. 2013, 27, 1647-1656.
8. Nakazawa, T.; Banba, K.; Hata, K.; Nihei, Y.; Hoshikawa, A.; Ohsawa, K. Metabolites of hirsuteine and hirsutine, the major indole alkaloids of Uncaria rhynchophylla, in rats. Biol. Pharm. Bull. 2006, 29, 1671-1677.
9. Le Verge, R.; Le Corre, P.; Chevanne, F.; Döe De Maindreville, M.; Royer, D.; Levy, J. Determination of yohimbine and its two hydroxylated metabolites in humans by high-performance liquid chromatography and mass spectral analysis. J. Chromatogr. B: Biomed. Sci. Appl. 1992, 574, 283-292.
10. Berlan, M.; Le Verge, R.; Galitzky, J.; Le Corre, P. Alpha 2-adrenoceptor antagonist potencies of two hydroxylated metabolites of yohimbine. Br. J. Pharmacol. 1993, 108, 927-932.
11. Gai, Y.; Chen, H.; Liu, W.; Feng, F.; Xie, N. The metabolism of YiGan San and subsequent pharmacokinetic evaluation of four metabolites in rat based on liquid chromatography with tandem mass spectrometry. J. Chromatogr. B 2014, 972, 22-28.
12. Castro-Perez, J.M. Current and future trends in the application of HPLC-MS to metabolite-identification studies. Drug Discov. Today 2007, 12, 249-256.
13. Yuzurihara, M.; Ikarashi, Y.; Goto, K.; Sakakibara, I.; Hayakawa, T.; Sasaki, H. Geissoschizine methyl ether, an indole alkaloid extracted from Uncariae Ramulus et Uncus, is a potent vasorelaxant of isolated rat aorta. Eur. J. Pharmacol. 2002, 444, 183-189.
14. Deiters, A.; Chen, K.; Eary, C.T.; Martin, S.F. Biomimetic entry to the sarpagan family of indole alkaloids: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine. J. Am. Chem. Soc. 2003, 125, 4541-4550.