Two New Alkaloids of the Crinane Series from Pancratium sickenbergeri

Abou‐Donia, Amina H.; Amer, Masouda E.; Darwish, Fikria A.; Kassem, Fahima F.; Hammoda, Hala M.; Abdel‐Kader, Maged S.; Bin, Zhou; Kingston, David G. I.

doi:10.1055/s-2002-26754

Cited by 22 publications

(8 citation statements)

References 9 publications

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“…In this case the steric encumbrance associated with the two acetyl groups may lead to their significantly slower hydrolysis. Finally, 11-hydroxyvittatine (20), a demethylated natural congener of cytotoxic haemanthamine (19), was reported to have no antiproliferative activity [47]. We also observed only a modest activity in the MTT assay and no induction of apoptosis as opposed to 19, demonstrating that the methyl ether is an important part of the cytotoxic pharmacophore.…”

Section: Resultsmentioning

confidence: 64%

Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

et al. 2009

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Twenty nine Amaryllidaceae alkaloids and their derivatives belonging to five most common groups, including lycorine-, lycorenine-, tazettine-, crinine-, and narciclasine-types, were evaluated for antiproliferative, apoptosis inducing and antiinvasive activities in vitro. The antiproliferative properties of each test compound are in agreement with those reported in the literature, while the high potency of amarbellisine is reported for the first time. It was also found that with the exception of ungeremine, amarbellisine and hippeastrine, the antiproliferative effect of the potent compounds is apoptosis-mediated. Thus, apoptosis in Jurkat cells was triggered by narciclasine, narciclasine tetraacetate, C10b-R-hydroxypancratistatin, cis-dihydronarciclasine, trans-dihydronarciclasine, lycorine, 1-O-acetyllycorine, lycorine-2-one, pseudolycorine, and haemanthamine. With the exception of narciclasine, lycorine and haemanthamine, the apoptosis inducing properties of these compounds are reported for the first time. The collagen type I invasion assay revealed potent antiinvasive properties associated with N-methyllycorine iodide, hippeastrine, clivimine, buphanamine, and narciclasine tetraacetate, all of which were tested at non-toxic concentrations. The antiinvasive activity of buphanamine is particularly promising since this alkaloid is not toxic to cells even at much higher doses. This work has resulted in identification of several novel leads for anticancer drug design.

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Section: Resultsmentioning

confidence: 64%

Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

et al. 2009

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“…After saturation of the C C bonds of alkaloids 2a over Pd/C, four dihydrocrinine-type alkaloids were obtained: (–)-dihydrocrinine, 15 (+)-dihydrovittatine, 16 (+)-dihydroepivittatine, 17 and (–)-dihydroepicrinine. 17 By debenzylation of alkaloids 2c with boron trichloride (BCl 3 ), four naturally occurring crinine-type alkaloids were obtained: (+)-8- O -demethylmaritidine, 18 (–)-8- O -demethylmaritidine, 19 (+)-siculine, 16 and (–)-siculine. 20 …”

Section: Resultsmentioning

confidence: 99%

Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones

et al. 2017

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“…The known metabolites were determined to be lycorine (2) [28], hippadine (3) [29], (−)8-demethylmaritidine (4) [30], pratorinine (5) [31], (+)-vittatine (6) [32], and and (-)-marithamine (7) [33] four methylene carbons at [δ C 32.5 (C-4), 60.9 (C-6), 43.6 (C-11), and 54.9 (C-12)]; two methine carbons at [δ C 64.6 (C-3) and 63.9 (C-4a)]; and one methoxy carbon at [δ C 56.7 (OCH 3 )]. The 1 H and 13 C NMR data of 1 were similar to those of (−)8-demethylmaritidine (5), except for a difference in the chemical shift at the H-7 position [30]. The structure of 1 was deduced as a dimer of (−)8-demethylmaritidine (4) via a link between C-7 and C-7'.…”

Section: Resultsmentioning

confidence: 99%

Acetylcholinesterase inhibition studies of alkaloid components from Crinum asiaticum var. sinicum plants: In vitro assessments by molecular docking and molecular dynamics simulations

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et al. 2023

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Alkaloids are among the most important and best-known secondary metabolites as sources of new drugs from medicinal plants and marine organisms. A phytochemical investigation of whole Crinum asiaticum var. sinicum plants resulted in the isolation of seven alkaloids (1–7), including one new compound (1). Their structures were elucidated using NMR and HR-ESI-MS. The absolute configuration of 1 was established by ECD. A molecular docking and molecular dynamics simulation was carried out for the isolated compounds to screen for acetylcholine (AChE) inhibitory activity. The target compounds were evaluated for their inhibitory effects on AChE activity in vitro. The results suggest that these C. asiaticum alkaloids possess the ability to treat Alzheimer’s disease.

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Two New Alkaloids of the Crinane Series from Pancratium sickenbergeri

Abstract: Two new alkaloids; ent-6alpha/6beta-hydroxybuphanisine, (-)-8-demethylmaritidine and seven known alkaloids were isolated from Pancratium sickenbergeri grown in Egypt. Three of the known alkaloids were tested in the NCI cytotoxicity screen, but were found to be inactive.

Cited by 22 publications

References 9 publications

Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones

Acetylcholinesterase inhibition studies of alkaloid components from Crinum asiaticum var. sinicum plants: In vitro assessments by molecular docking and molecular dynamics simulations

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