FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W4295432908> ?p ?o ?g. }

• W4295432908 endingPage "2216" @default.
• W4295432908 startingPage "2207" @default.
• W4295432908 abstract "Examination of the MeOH extract of the sponge, Pseudoceratina cf. verrucosa, Berquist 1995 collected near Ningaloo Reef, Western Australia for selective acetylcholinesterase (AChE) inhibitors, yielded five new bromotyrosine alkaloids, methyl purpuroceratates A and B (1b and 2b), purpuroceratic acid C (3a), and ningalamides A and B (4 and 5). The structures of 1-4 share the dibromo-spirocyclohexadienyl-isoxazoline (SIO) ring system found in purealidin-R, while ketoxime 5 is analogous to ianthelline and purpurealidin I. The planar structures of all five compounds were obtained from analysis of MS, 1D and 2D NMR data, and the absolute configuration of the spiroisoxazoline (SIO) unit was assigned by electronic circular dichroism (ECD) and comparison with standards prepared by total synthesis of methyl purpuroceratate C, (±)-3b. Compound 4 is the most complex SIO described, to date. The configuration of the homoserine module (C) in 4 was ascertained, after acid hydrolysis, by derivatization of an l-tryptophanamide derivative based on Marfey's reagent. Chiral-phase HPLC, with comparison to synthetic standards, revealed that most SIOs isolated from P. cf. verrucosa were configurationally heterogeneous; some, essentially racemic. Chiral-phase HPLC, with UV-ECD detection, is demonstrated as a superlative method for configurational assignment and quantitation of the enantiomeric composition of SIOs. Two SIOs─aerophobin-1 and aplysinamisine II─emerged as selective inhibitors of AChE over butyrylcholinesterase (BuChE, IC50 ratio >10), while aplysamine-2 moderately inhibited both cholinesterases (ChEs, IC50, (AChE) 0.46 μM; IC50, (BuChE) 1.03 μM). SIO alkaloids represent a potential new structural manifold for lead-discovery of new therapeutics for treatment of Alzheimer's disease." @default.
• W4295432908 created "2022-09-14" @default.
• W4295432908 creator A5028201886 @default.
• W4295432908 creator A5056958049 @default.
• W4295432908 creator A5072289043 @default.
• W4295432908 date "2022-09-12" @default.
• W4295432908 modified "2023-09-26" @default.
• W4295432908 title "Spiroisoxazoline Inhibitors of Acetylcholinesterase from <i>Pseudoceratina verrucosa</i>. Quantitative Chiroptical Analysis of Configurational Heterogeneity, and Total Synthesis of (±)-Methyl Purpuroceratate C" @default.
• W4295432908 cites W1489754066 @default.
• W4295432908 cites W1970138128 @default.
• W4295432908 cites W1971048984 @default.
• W4295432908 cites W1972649718 @default.
• W4295432908 cites W1976122220 @default.
• W4295432908 cites W1978179512 @default.
• W4295432908 cites W2005692768 @default.
• W4295432908 cites W2005802017 @default.
• W4295432908 cites W2011358475 @default.
• W4295432908 cites W2013822199 @default.
• W4295432908 cites W2047701750 @default.
• W4295432908 cites W2049112039 @default.
• W4295432908 cites W2058620107 @default.
• W4295432908 cites W2061241470 @default.
• W4295432908 cites W2072698994 @default.
• W4295432908 cites W2080389975 @default.
• W4295432908 cites W2081729393 @default.
• W4295432908 cites W2085648915 @default.
• W4295432908 cites W2086684724 @default.
• W4295432908 cites W2087563815 @default.
• W4295432908 cites W2089863567 @default.
• W4295432908 cites W2092706714 @default.
• W4295432908 cites W2105975722 @default.
• W4295432908 cites W2144591655 @default.
• W4295432908 cites W2173835695 @default.
• W4295432908 cites W2270488845 @default.
• W4295432908 cites W2316542294 @default.
• W4295432908 cites W2320227236 @default.
• W4295432908 cites W2326842020 @default.
• W4295432908 cites W2572754060 @default.
• W4295432908 cites W2588038427 @default.
• W4295432908 cites W2746344529 @default.
• W4295432908 cites W2949320061 @default.
• W4295432908 cites W2951367773 @default.
• W4295432908 cites W3023827559 @default.
• W4295432908 cites W3137886146 @default.
• W4295432908 doi "https://doi.org/10.1021/acs.jnatprod.2c00595" @default.
• W4295432908 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/36095307" @default.
• W4295432908 hasPublicationYear "2022" @default.
• W4295432908 type Work @default.
• W4295432908 citedByCount "0" @default.
• W4295432908 crossrefType "journal-article" @default.
• W4295432908 hasAuthorship W4295432908A5028201886 @default.
• W4295432908 hasAuthorship W4295432908A5056958049 @default.
• W4295432908 hasAuthorship W4295432908A5072289043 @default.
• W4295432908 hasConcept C121332964 @default.
• W4295432908 hasConcept C124668440 @default.
• W4295432908 hasConcept C129694887 @default.
• W4295432908 hasConcept C133571119 @default.
• W4295432908 hasConcept C178790620 @default.
• W4295432908 hasConcept C179998833 @default.
• W4295432908 hasConcept C181199279 @default.
• W4295432908 hasConcept C185592680 @default.
• W4295432908 hasConcept C20621625 @default.
• W4295432908 hasConcept C25170562 @default.
• W4295432908 hasConcept C2776923573 @default.
• W4295432908 hasConcept C2778816929 @default.
• W4295432908 hasConcept C32909587 @default.
• W4295432908 hasConcept C43617362 @default.
• W4295432908 hasConcept C486523 @default.
• W4295432908 hasConcept C52703039 @default.
• W4295432908 hasConcept C62520636 @default.
• W4295432908 hasConcept C71240020 @default.
• W4295432908 hasConcept C7602139 @default.
• W4295432908 hasConceptScore W4295432908C121332964 @default.
• W4295432908 hasConceptScore W4295432908C124668440 @default.
• W4295432908 hasConceptScore W4295432908C129694887 @default.
• W4295432908 hasConceptScore W4295432908C133571119 @default.
• W4295432908 hasConceptScore W4295432908C178790620 @default.
• W4295432908 hasConceptScore W4295432908C179998833 @default.
• W4295432908 hasConceptScore W4295432908C181199279 @default.
• W4295432908 hasConceptScore W4295432908C185592680 @default.
• W4295432908 hasConceptScore W4295432908C20621625 @default.
• W4295432908 hasConceptScore W4295432908C25170562 @default.
• W4295432908 hasConceptScore W4295432908C2776923573 @default.
• W4295432908 hasConceptScore W4295432908C2778816929 @default.
• W4295432908 hasConceptScore W4295432908C32909587 @default.
• W4295432908 hasConceptScore W4295432908C43617362 @default.
• W4295432908 hasConceptScore W4295432908C486523 @default.
• W4295432908 hasConceptScore W4295432908C52703039 @default.
• W4295432908 hasConceptScore W4295432908C62520636 @default.
• W4295432908 hasConceptScore W4295432908C71240020 @default.
• W4295432908 hasConceptScore W4295432908C7602139 @default.
• W4295432908 hasFunder F4320337355 @default.
• W4295432908 hasFunder F4320337358 @default.
• W4295432908 hasIssue "9" @default.
• W4295432908 hasLocation W42954329081 @default.
• W4295432908 hasLocation W42954329082 @default.
• W4295432908 hasOpenAccess W4295432908 @default.
• W4295432908 hasPrimaryLocation W42954329081 @default.

• next