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  • Spatial Distribution and Stability of Cholinesterase Inhibitory Protoberberine Alkaloids from Papaver setiferum

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    Author(s)
    Safa, Neda
    Trobec, Tomaž
    Holland, Darren C
    Slazak, Blazej
    Jacobsson, Erik
    Hawkes, Jeffrey A
    Frangež, Robert
    Sepčić, Kristina
    Göransson, Ulf
    Moodie, Lindon WK
    Robertson, Luke P
    Griffith University Author(s)
    Holland, Darren C.
    Year published
    2021
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    Abstract
    During a research program to identify new cholinesterase inhibitors of natural origin, two new 7,8-didehydroprotoberberine alkaloids (1 and 2) and nine known compounds (3-11) were isolated from the capsules of the common ornamental poppy, Papaver setiferum (previously P. pseudo-orientale). Despite their reported instability, the 7,8-didehydroprotoberberines isolated herein appeared relatively stable, particularly as their trifluoroacetic acid salts. The spatial distributions of the isolated alkaloids were also analyzed using desorption electrospray ionization imaging mass spectrometry. The alkaloids were localized predominantly ...
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    During a research program to identify new cholinesterase inhibitors of natural origin, two new 7,8-didehydroprotoberberine alkaloids (1 and 2) and nine known compounds (3-11) were isolated from the capsules of the common ornamental poppy, Papaver setiferum (previously P. pseudo-orientale). Despite their reported instability, the 7,8-didehydroprotoberberines isolated herein appeared relatively stable, particularly as their trifluoroacetic acid salts. The spatial distributions of the isolated alkaloids were also analyzed using desorption electrospray ionization imaging mass spectrometry. The alkaloids were localized predominantly within the walls and vascular bundles of the capsules, with the highest relative abundances occurring in the lower half of the capsules toward the peduncle. The relative abundances of the alkaloids were also compared across plant development stages. Although most alkaloids did not show clear patterns in their concentration across development stages, the concentration of suspected oxidation products clearly spiked upon plant death. Finally, all isolated natural products were screened for inhibitory activities against a panel of cholinesterases, from both human and animal sources. These studies identified several competitive inhibitors of cholinesterases with potency in the low micromolar range (1-4, 6, 7), offering new lead compounds for the development of cholinesterase inhibitory drugs.
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    Journal Title
    Journal of Natural Products
    DOI
    https://doi.org/10.1021/acs.jnatprod.1c00980
    Copyright Statement
    © 2021 The Authors. Published by American Chemical Society and American Society of Pharmacognosy. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
    Note
    This publication has been entered as an advanced online version in Griffith Research Online.
    Subject
    Chemical sciences
    Biological sciences
    Publication URI
    http://hdl.handle.net/10072/411287
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    • Journal articles

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