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.

Basic information

Original name

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

Authors

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 Czech Republic, belonging to the institution), R. PERINOVA, K. BREITEROVA, J. KUNES, L. NOVAKOVA, L. OPLETAL and L. CAHLIKOVA (guarantor)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.307

RIV identification code

RIV/00216224:14160/21:00122468

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

000618103400009

Keywords in English

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

Abstract

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 and 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, vol. 107, No 104567, p. 1-11. ISSN 0045-2068. Available from: 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 and 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, vol.~107, No~104567, p.~1-11. ISSN~0045-2068. Available from: https://dx.doi.org/10.1016/j.bioorg.2020.104567.

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