Amaryllidaceae alkaloids from Hippeastrum X Hybridum CV. Ferrari, and preparation of vittatine derivatives as potential ligands for Alzheimer's disease

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F21%3A50018769" target="_blank" >RIV/62690094:18470/21:50018769 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60162694:G44__/21:00556279 RIV/00179906:_____/21:10434864 RIV/00216208:11160/21:10434864

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0254629920309613?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0254629920309613?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.sajb.2020.06.024" target="_blank" >10.1016/j.sajb.2020.06.024</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Amaryllidaceae alkaloids from Hippeastrum X Hybridum CV. Ferrari, and preparation of vittatine derivatives as potential ligands for Alzheimer's disease

Popis výsledku v původním jazyce

Fourteen (1-14) known Amaryllidaceae alkaloids, of various structural types, have been isolated from fresh bulbs of Hippeastrum X hybridum cv. Ferrari. The chemical structures were identified by various spectroscopic (1D and 2D NMR) and mass spectrometric (GC-MS, LC-MS) methods, and by comparison with literature data. Isolated alkaloids which, up to this date have not been studied for their inhibition potency against AChE, BuChE and POP, were screened in vitro for these inhibition activities. Unfortunatelly, all natural alkaloids were inactive in the AChE/BuChE assay; only zephyranthine (14) displayed moderate inhibition activity agains POP with an IC50 value of 142 +/- 10 mu M. Moreover, twelve new derivatives of the haemanthamine-type alkaloid vittatine (7), isolated in gram amounts from Hippeastrum cv. Ferrari, have been designed, synthesized and tested in vitro with particular emphasis on the treatment of neurodegenerative diseases. Some of the tested compounds revealed an intriguing selective hBuChE inhibitory profile with single-digit micro-molar IC50 values. The strongest hBuChE inhibition was demonstrated by 3-O-(2-methylbenzoyl)vittatine (7b), 3-O-(2-nitrobenzoyl)vittatine (7h) and 3-O-(2-chlorbenzoyl)vittatine (7m) with IC50 values 8.0 +/- 0.1 mM, 1.4 +/- 0.1 mM and 5.4 +/- 0.1 mM, respectively. The mode of hBuChE inhibition was minutely inspected using enzyme kinetic analysis in tandem with in silico experiments, the latter elucidating crucial interaction in 7b-, 7h-, and 7m-hBuChE complexes. (C) 2020 SAAB. Published by Elsevier B.V. All rights reserved.

Název v anglickém jazyce

Amaryllidaceae alkaloids from Hippeastrum X Hybridum CV. Ferrari, and preparation of vittatine derivatives as potential ligands for Alzheimer's disease

Popis výsledku anglicky

Fourteen (1-14) known Amaryllidaceae alkaloids, of various structural types, have been isolated from fresh bulbs of Hippeastrum X hybridum cv. Ferrari. The chemical structures were identified by various spectroscopic (1D and 2D NMR) and mass spectrometric (GC-MS, LC-MS) methods, and by comparison with literature data. Isolated alkaloids which, up to this date have not been studied for their inhibition potency against AChE, BuChE and POP, were screened in vitro for these inhibition activities. Unfortunatelly, all natural alkaloids were inactive in the AChE/BuChE assay; only zephyranthine (14) displayed moderate inhibition activity agains POP with an IC50 value of 142 +/- 10 mu M. Moreover, twelve new derivatives of the haemanthamine-type alkaloid vittatine (7), isolated in gram amounts from Hippeastrum cv. Ferrari, have been designed, synthesized and tested in vitro with particular emphasis on the treatment of neurodegenerative diseases. Some of the tested compounds revealed an intriguing selective hBuChE inhibitory profile with single-digit micro-molar IC50 values. The strongest hBuChE inhibition was demonstrated by 3-O-(2-methylbenzoyl)vittatine (7b), 3-O-(2-nitrobenzoyl)vittatine (7h) and 3-O-(2-chlorbenzoyl)vittatine (7m) with IC50 values 8.0 +/- 0.1 mM, 1.4 +/- 0.1 mM and 5.4 +/- 0.1 mM, respectively. The mode of hBuChE inhibition was minutely inspected using enzyme kinetic analysis in tandem with in silico experiments, the latter elucidating crucial interaction in 7b-, 7h-, and 7m-hBuChE complexes. (C) 2020 SAAB. Published by Elsevier B.V. All rights reserved.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EF16_019%2F0000841" target="_blank" >EF16_019/0000841: Zvýšení účinnosti a bezpečnosti léčiv a nutraceutik: moderní metody - nové výzvy</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

South African Journal of Botany

ISSN

0254-6299

e-ISSN

—

Svazek periodika

136

Číslo periodika v rámci svazku

JANUARY

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

10

Strana od-do

137-146

Kód UT WoS článku

000681444300019

EID výsledku v databázi Scopus

2-s2.0-85087745541