Amaryllidaceae alkaloids from Hippeastrum X Hybridum CV. Ferrari, and preparation of vittatine derivatives as potential ligands for Alzheimer's disease
The result's identifiers
Result code in 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>
Alternative codes found
RIV/60162694:G44__/21:00556279 RIV/00179906:_____/21:10434864 RIV/00216208:11160/21:10434864
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Amaryllidaceae alkaloids from Hippeastrum X Hybridum CV. Ferrari, and preparation of vittatine derivatives as potential ligands for Alzheimer's disease
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/EF16_019%2F0000841" target="_blank" >EF16_019/0000841: Efficiency and safety improvement of current drugs and nutraceuticals: advanced methods - new challenges</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
South African Journal of Botany
ISSN
0254-6299
e-ISSN
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Volume of the periodical
136
Issue of the periodical within the volume
JANUARY
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
10
Pages from-to
137-146
UT code for WoS article
000681444300019
EID of the result in the Scopus database
2-s2.0-85087745541