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

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 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.

Natural or artificial: An example of topographic spatial distribution analysis of mescaline in cactus plants by matrix-assisted laser desorption/ionization mass spectrometry imaging

“…The flat sample surface required by MALDI analysis was obtained by treating each part as follows: The pistils were first cut in half. The sepals, petals, stamens, and pistil halves were then flattened, sandwiched between two layers of air-laid paper (Kimberly-Clark Professional, USA), and pressed in a book to make a "bookmark" (Safa et al, 2022). The bookmarked sepals, petals, stamens, and pistil halves were then pasted onto the surface of ITO-coated conductive glass slides with double-sided carbon conductive tape.…”

Mass Spectrometry-Imaging Analysis of Active Ingredients in the Leaves of Taxus cuspidata

“…There are two morphologically and functionally distinct cell types: bundle sheath cells and mesophyll cells that surround the bundle sheath layer, which consists of the vascular bundles . In Papaver setiferum leaves, the alkaloids were predominantly localized within the walls and vascular bundles of the capsules . Isocolumbin is a natural alkaloids targeting the epidermal growth factor receptor in nonsmall cell lung cancer .…”

“… 38 In Papaver setiferum leaves, the alkaloids were predominantly localized within the walls and vascular bundles of the capsules. 39 Isocolumbin is a natural alkaloids targeting the epidermal growth factor receptor in nonsmall cell lung cancer. 40 Gartanin, which is first identified in the purple mangosteen fruit, is a potent growth inhibitor of various cancer cell lines.…”

How to sample a seizure plant: the role of the visualization spatial distribution analysis of Lophophora williamsii as an example

“…This result also has wide applicability to extrapolation to other plants. For example, in cannabis plants, Δ 9 -tetrahydrocannabinol (THC) is concentrated in the flowers and robust leaves (shoots) [ 73–75 ]; for opioids, the alkaloids are localized predominantly within the walls and vascular bundles of the capsules of Papaver setiferum , with the highest relative abundances occurring in the lower half of the capsules, toward the peduncle [ 76 ]. Tryptamines, represented by N,N -dimethyltryptamine, accumulate in tissues such as bark that forms a defensive epidermis and carries out important nutrient transport [ 77 , 78 ].…”