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Molecules 2016, 21(7), 923;

Evaluation of the Antidepressant Activity, Hepatotoxicity and Blood Brain Barrier Permeability of Methyl Genipin

1,2,3,* , 1,2,3
School of Pharmacy, Yantai University, Yantai 264005, China
Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Yantai 264005, China
Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai 264005, China
Author to whom correspondence should be addressed.
Academic Editor: Diego Muñoz-Torrero
Received: 24 May 2016 / Revised: 8 July 2016 / Accepted: 12 July 2016 / Published: 16 July 2016
(This article belongs to the Section Medicinal Chemistry)
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Geniposide (GE) is the main bioactive component of Gardeniae Fructus. The hepatotoxicity of geniposide limited clinical application. In order to get a new geniposide derivative that has less hepatotoxicity and still possesses the antidepressant activity, a new C-1 hydroxyl methylation derivative named methyl genipin (MG) was synthesized from geniposide. In the present study, we demonstrated that MG did not increase the liver index, alanine aminotransferase (ALT) and aspirate aminotransferase (AST). Histopathological examination suggested that no toxic damages were observed in rats treated orally with MG (0.72 mmol/kg). More importantly, a 7-day treatment with MG at 0.13, 0.26, and 0.52 mmol/kg/day could reduce the duration of immobility. It showed that the antidepressant-like effects of MG were similar to GE in the tail suspension test and the forced swim test. Furthermore, we found MG could be detected in the brain homogenate of mice treated orally with MG 0.52 mmol/kg/day for 1 day by HPLC. The area under the curve (AUC) of MG in the brain homogenate was enhanced to 21.7 times that of GE. The brain amount and distribution speed of MG were improved significantly after oral administration. This study demonstrated that MG possessed the antidepressant effects and could cross the blood–brain barrier, but had less hepatotoxicity. View Full-Text
Keywords: geniposide derivative; antidepressant effect; hepatotoxicity; blood–brain barrier geniposide derivative; antidepressant effect; hepatotoxicity; blood–brain barrier

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Che, X.; Wang, M.; Wang, T.; Fan, H.; Yang, M.; Wang, W.; Xu, H. Evaluation of the Antidepressant Activity, Hepatotoxicity and Blood Brain Barrier Permeability of Methyl Genipin. Molecules 2016, 21, 923.

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