RESUMO
The chemical compositions of essential oils (EOs) prepared from six spices including cinnamon, amomum tsao-ko, cardamom, amomum, black pepper and white pepper were analyzed by gas chromatography-mass spectrometry (GC/MS), which led to identify almost 200 volatile compounds. All EOs of spices showed cholinesterase inhibitory activity. Among them, pepper EO showed most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values of 8.54â µg/mL (black pepper EO) and 5.02â µg/mL (white pepper EO). Molecular docking and inâ vitro validation suggested that 3-carene, α-pinene and ß-pinene with IC50 value of 1.73, 2.66, and 14.75â µg/mL, respectively, might be active constituents of spices oil in inhibiting AChE. Furthermore, amomum tsao-ko EO and amomum EO can improve behavioral disorder in dementia zebrafish induced by aluminum trichloride (AlCl3 ).
Assuntos
Amomum/química , Inibidores da Colinesterase/química , Elettaria/química , Óleos Voláteis/química , Piper nigrum/química , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Cloreto de Alumínio/toxicidade , Amomum/metabolismo , Animais , Comportamento Animal/efeitos dos fármacos , Sítios de Ligação , Inibidores da Colinesterase/metabolismo , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/uso terapêutico , Demência/induzido quimicamente , Demência/tratamento farmacológico , Modelos Animais de Doenças , Elettaria/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Simulação de Acoplamento Molecular , Óleos Voláteis/metabolismo , Óleos Voláteis/farmacologia , Óleos Voláteis/uso terapêutico , Piper nigrum/metabolismo , Peixe-ZebraRESUMO
A pair of stereoisomers of new 4,5-dihydroxypiperine was isolated from P. retrofractum and showed profound activity on AlCl3-induced dementia. In order to determine their absolute configurations and biological activities, all four possible stereoisomers of 4,5-dihydroxypiperine were synthesized from piperidine by Sharpless asymmetric dihydroxylation and Mitsunobu reaction. Their absolute configurations were established as (4R,5R) (1), (4S,5S) (2), (4S,5R) (3) and (4R,5S) (4) by NMR, optical rotation and CD spectra. It is note that only compound 4 improved behavioral disorder in AlCl3-induced dementia. Accordingly, the pair of stereoisomers isolated from P. retrofractum was determined to be (4S,5S) and (4R,5S)-isomers (2 and 4). The ratio of the epimers was present as 1:0.7 (4:2).