69977-52-2Relevant articles and documents
Evaluation of the antidepressant activity, hepatotoxicity and blood brain barrier permeability of methyl genipin
Che, Xin,Wang, Meiyu,Wang, Tian,Fan, Huaying,Yang, Mingyan,Wang, Wenyan,Xu, Hui
, (2016)
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.
1-O-alkyl genipin and preparation method and application thereof
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Paragraph 0136; 0146-0151, (2022/01/04)
The invention belongs to the technical field of genipin derivative synthesis, and particularly relates to 1-O-alkyl genipin and a preparation method and application thereof. The invention provides the preparation method of 1-O-alkyl genipin, the preparation method comprises the following steps: mixing a raw material A, low-carbon alcohol, a Lewis acid catalyst and a polar organic solvent, and carrying out an alkoxylation reaction to obtain 1-O-alkyl genipin, the raw material A comprising genipin and/or 10-O-Piv-1-O-NHCCl3 genipin. In the 1-O-alkyl genipin obtained by the preparation method, the conformation of the 1R-O-alkyl genipin is dominant, and the neuroprotective activity is higher.
Design, synthesis, and evaluation of genipin derivatives for the treatment of Alzheimer's Disease
Huang, Weijun,Wang, Yujun,Li, Jiaming,Zhang, Yanchun,Ma, Xiaodong,Zhu, Panhu,Zhang, Yang
, p. 110 - 122 (2018/12/11)
Twenty-two novel genipin derivatives have been designed, synthesized, and evaluated for their inhibitory activity against acetylcholinesterase (AChE). As a result, compound 13a bearing ligustrazine moiety displayed the most potent AChE inhibitory activity in this series with IC50 value of 218?nm. Besides, MTT assay was performed to investigate the neuroprotection of these compounds against PC12 cells injured by Amyloid β-protein 1–42 (Aβ1–42). Among them, 8a showed higher inhibition rate (%Inhibition?=?22.29) than the positive reference Donepezil (%Inhibition?=?17.65).
