Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their
implication to Alzheimer's disease: Isolation, structural
elucidation and biological activity

J 2021

Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity

KOHELOVA, E., J. MARIKOVA, J. KORABECNY, D. HULCOVA, T. KUCERA et. al.

Základní údaje

Originální název

Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity

Autoři

KOHELOVA, E., J. MARIKOVA, J. KORABECNY, D. HULCOVA, T. KUCERA, D. JUN, J. CHLEBEK, J. JENCO, M. SAFRATOVA, M. HRABINOVA, A. RITOMSKA, Milan MALANÍK (203 Česká republika, domácí), R. PERINOVA, K. BREITEROVA, J. KUNES, L. NOVAKOVA, L. OPLETAL a L. CAHLIKOVA (garant)

Vydání

Bioorganic Chemistry, SAN DIEGO, ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, 0045-2068

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.307

Kód RIV

RIV/00216224:14160/21:00122468

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1016/j.bioorg.2020.104567

UT WoS

000618103400009

Klíčová slova anglicky

Zephyranthes citrina; Amaryllidaceae; Alkaloids; Narcieliine; Alzheimer's disease; Docking studies

Štítky

rivok, ÚPL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 23. 3. 2022 16:37, JUDr. Sabina Krejčiříková

Anotace

V originále

Twenty known Amaryllidaceae alkaloids of various structural types, and one undescribed alkaloid of narcikachnine-type, named narcieliine (3), have been isolated from fresh bulbs of Zephyranthes citrina. The chemical structures of the isolated alkaloids were elucidated by a combination of MS, HRMS, 1D and 2D NMR, and CD spectroscopic techniques, and by comparison with literature data. The absolute configuration of narcieliine (3) has also been determined. Compounds isolated in a sufficient quantity were evaluated for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7), butyrylcholinesterase (BuChE; E.C. 3.1.1.8), and prolyl oligopeptidase (POP; E.C. 3.4.21.26) inhibition activities. Significant human AChE/BuChE (hAChE/hBuChE) inhibitory activity was demonstrated by the newly described alkaloid narcieliine (3), with IC50 values of 18.7 +/- 2.3 mu M and 1.34 +/- 0.31 mu M, respectively. This compound is also predicted to cross the blood-brain barrier (BBB) through passive diffusion. The in vitro data were further supported by in silico studies of 3 in the active site of hAChE/hBuChE.

Citovat

KOHELOVA, E., J. MARIKOVA, J. KORABECNY, D. HULCOVA, T. KUCERA, D. JUN, J. CHLEBEK, J. JENCO, M. SAFRATOVA, M. HRABINOVA, A. RITOMSKA, Milan MALANÍK, R. PERINOVA, K. BREITEROVA, J. KUNES, L. NOVAKOVA, L. OPLETAL a L. CAHLIKOVA. Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity. Bioorganic Chemistry. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, roč. 107, č. 104567, s. 1-11. ISSN 0045-2068. Dostupné z: https://dx.doi.org/10.1016/j.bioorg.2020.104567.

@article{1794937,
   author = {Kohelova, E. and Marikova, J. and Korabecny, J. and Hulcova, D. and Kucera, T. and Jun, D. and Chlebek, J. and Jenco, J. and Safratova, M. and Hrabinova, M. and Ritomska, A. and Malaník, Milan and Perinova, R. and Breiterova, K. and Kunes, J. and Novakova, L. and Opletal, L. and Cahlikova, L.},
   article_location = {SAN DIEGO},
   article_number = {104567},
   doi = {http://dx.doi.org/10.1016/j.bioorg.2020.104567},
   keywords = {Zephyranthes citrina; Amaryllidaceae; Alkaloids; Narcieliine; Alzheimer's disease; Docking studies},
   language = {eng},
   issn = {0045-2068},
   journal = {Bioorganic Chemistry},
   title = {Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity},
   url = {https://reader.elsevier.com/reader/sd/pii/S0045206820318654?token=5E47B1A8AADF6BF05D1AAF363BAF7C93AC087C9BDDAE841A51EAC2BBE4E3BF467F787C1AC7BE0F078B20D8FC896C9179&originRegion=eu-west-1&originCreation=20210930052405},
   volume = {107},
   year = {2021}
}

TY  - JOUR
ID  - 1794937
AU  - Kohelova, E. - Marikova, J. - Korabecny, J. - Hulcova, D. - Kucera, T. - Jun, D. - Chlebek, J. - Jenco, J. - Safratova, M. - Hrabinova, M. - Ritomska, A. - Malaník, Milan - Perinova, R. - Breiterova, K. - Kunes, J. - Novakova, L. - Opletal, L. - Cahlikova, L.
PY  - 2021
TI  - Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity
JF  - Bioorganic Chemistry
VL  - 107
IS  - 104567
SP  - 1-11
EP  - 1-11
PB  - ACADEMIC PRESS INC ELSEVIER SCIENCE
SN  - 00452068
KW  - Zephyranthes citrina
KW  - Amaryllidaceae
KW  - Alkaloids
KW  - Narcieliine
KW  - Alzheimer's disease
KW  - Docking studies
UR  - https://reader.elsevier.com/reader/sd/pii/S0045206820318654?token=5E47B1A8AADF6BF05D1AAF363BAF7C93AC087C9BDDAE841A51EAC2BBE4E3BF467F787C1AC7BE0F078B20D8FC896C9179&originRegion=eu-west-1&originCreation=20210930052405
N2  - Twenty known Amaryllidaceae alkaloids of various structural types, and one undescribed alkaloid of narcikachnine-type, named narcieliine (3), have been isolated from fresh bulbs of Zephyranthes citrina. The chemical structures of the isolated alkaloids were elucidated by a combination of MS, HRMS, 1D and 2D NMR, and CD spectroscopic techniques, and by comparison with literature data. The absolute configuration of narcieliine (3) has also been determined. Compounds isolated in a sufficient quantity were evaluated for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7), butyrylcholinesterase (BuChE; E.C. 3.1.1.8), and prolyl oligopeptidase (POP; E.C. 3.4.21.26) inhibition activities. Significant human AChE/BuChE (hAChE/hBuChE) inhibitory activity was demonstrated by the newly described alkaloid narcieliine (3), with IC50 values of 18.7 +/- 2.3 mu M and 1.34 +/- 0.31 mu M, respectively. This compound is also predicted to cross the blood-brain barrier (BBB) through passive diffusion. The in vitro data were further supported by in silico studies of 3 in the active site of hAChE/hBuChE.
ER  -

KOHELOVA, E., J. MARIKOVA, J. KORABECNY, D. HULCOVA, T. KUCERA, D. JUN, J. CHLEBEK, J. JENCO, M. SAFRATOVA, M. HRABINOVA, A. RITOMSKA, Milan MALANÍK, R. PERINOVA, K. BREITEROVA, J. KUNES, L. NOVAKOVA, L. OPLETAL a L. CAHLIKOVA. Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity. \textit{Bioorganic Chemistry}. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2021, roč.~107, č.~104567, s.~1-11. ISSN~0045-2068. Dostupné z: https://dx.doi.org/10.1016/j.bioorg.2020.104567.

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