Catechol alkenyls from Semecarpus anacardium: Acetylcholinesterase inhibition and binding mode predictions

Adhami, Hamid-Reza; Linder, Tobias; Kaehlig, Hanspeter; Schuster, Daniela; Zehl, Martin; Krenn, Liselotte

doi:10.1016/j.jep.2011.10.032

Cited by 41 publications

(12 citation statements)

References 29 publications

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“…Anisaldehyde-sulfuric acid was used as the detection reagent to determine the chemical composition of the extract [18]. In parallel, a TLC bioautography assay was performed for the AChE inhibitory activity according to a published method [19, 20]. The mobile phase was completely removed under airstream before detection.…”

Section: Methodsmentioning

confidence: 99%

“…A quantitative colorimetric assay based on Ellman’s method was used to measure the AChE inhibitory activities of the substances [20, 21]. Briefly, in a 96-well plate, 25 μL of 15 mM ATCI, 125 μL of 3 mM DTNB in buffer B, 50 μL of buffer A, and 25 μL of the extract or the isolated substances (from 15.6 μg/mL to 2.0 mg/mL in 10% DMSO) were thoroughly mixed and the absorbance was read at 405 nm five times every 15 s. Finally, 25 μL of AChE (0.22 U/mL in buffer A) were added and the plate was incubated at 25°C for 10 minutes.…”

Section: Methodsmentioning

confidence: 99%

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Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Adhami

Lütz²,

Kählig³

et al. 2013

Sci. Pharm.

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The use of herbal medicinal preparations in dementia therapy has been studied based on experience from traditional medicine. A dichloromethane extract of gum ammoniacum, the gum-resin from Dorema ammoniacum D. Don had shown acetylcholinesterase (AChE) inhibitory activity in a previous study. The aim of this study was the isolation and characterization of the active compounds from this resin. The extract was investigated by a respective colorimetric microplate assay and the active zones were identified via TLC bioautography and isolated using several chromatographic techniques. The structures of the active components were characterized by one- and two-dimensional 1H and 13C NMR spectroscopy and mass spectrometry as (2′S,5′S)-2′-ethenyl-5′-(3-hy-droxy-6-methyl-4-oxohept-5-en-2-yl)-7-methoxy-2′-methyl-4H-spiro[chromene-3,1′-cyclopentane]-2,4-dione (1), which is an analogue of doremone A and a new natural compound, and as (2′S,5′R)-2′-ethenyl-5′-[(2R,4R)-4-hydroxy-6-methyl-3-oxohept-5-en-2-yl]-7-methoxy-2′-methyl-4H-spiro[chromene-3,1′-cyclo-pentane]-2,4-dione (2 = doremone A), (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (3 = dshamirone), and 4,7-dihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2H-chromen-2-one (4 = am-moresinol). Dshamirone turned out to be the most active compound with an IC50 value for AChE inhibitory activity of 23.5 μM, whereas the other substances showed weak activity. The concentrations of the analytes in the resin were determined by HPLC as 3.1%, 4.6%, 1.9%, and 9.9%, respectively.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Adhami

Lütz²,

Kählig³

et al. 2013

Sci. Pharm.

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show abstract

“…It was also observed that anti-AChE activity dramatically decreased when the acidic and the phenolic hydroxy group were methylated. Two catechol alkenyls were isolated from the fruits of Semecarpus anacardium (Anacardiaceae), a species used in Ayurvedic medicine for retarding and treatment of memory loss [74]. Compounds 197 and 198 were identified as active components of the dichloromethane extract through a fractionation guided by the detection of AChE inhibition.…”

Section: Non-alkaloidal Compounds With Ache Inhibitory Activitymentioning

confidence: 99%

Natural AChE Inhibitors from Plants and their Contribution to Alzheimer’s Disease Therapy

et al. 2013

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As acetylcholinesterase (AChE) inhibitors are an important therapeutic strategy in Alzheimer’s disease, efforts are being made in search of new molecules with anti-AChE activity. The fact that naturally-occurring compounds from plants are considered to be a potential source of new inhibitors has led to the discovery of an important number of secondary metabolites and plant extracts with the ability of inhibiting the enzyme AChE, which, according to the cholinergic hypothesis, increases the levels of the neurotransmitter acetylcholine in the brain, thus improving cholinergic functions in patients with Alzheimer’s disease and alleviating the symptoms of this neurological disorder. This review summarizes a total of 128 studies which correspond to the most relevant research work published during 2006-2012 (1st semester) on plant-derived compounds, plant extracts and essential oils found to elicit AChE inhibition.

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“…The AChE inhibitory activities of the substances were measured by a quantitative colorimetric assay based on Ellman's method (Rhee et al ., ; Adhami et al ., ). In a 96‐well plate, 25 μL of 7.5 m m ATCI, 125 μL of 1.5 m m DTNB in buffer B, 50 μL of buffer A and 25 μL of the extract or the isolated substances (from 7.8 µg/mL to 1.0 mg/mL in 10% DMSO) were thoroughly mixed and the absorbance was read at 405 nm five times every 15 s. After addition of 25 μL of AChE (0.11 U/mL in buffer A) the plate was incubated at 25°C for 10 min and the absorbance was measured again every 15 s for eight times.…”

Section: Chemicals and Reagentsmentioning

confidence: 97%

Combination of Bioautography with HPTLC–MS/NMR: A Fast Identification of Acetylcholinesterase Inhibitors from Galbanum^†

Adhami

Scherer

Kaehlig

et al. 2013

Phytochemical Analysis

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Catechol alkenyls from Semecarpus anacardium: Acetylcholinesterase inhibition and binding mode predictions

Cited by 41 publications

References 29 publications

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Natural AChE Inhibitors from Plants and their Contribution to Alzheimer’s Disease Therapy

Combination of Bioautography with HPTLC–MS/NMR: A Fast Identification of Acetylcholinesterase Inhibitors from Galbanum^†

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Catechol alkenyls from Semecarpus anacardium: Acetylcholinesterase inhibition and binding mode predictions

Cited by 41 publications

References 29 publications

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Natural AChE Inhibitors from Plants and their Contribution to Alzheimer’s Disease Therapy

Combination of Bioautography with HPTLC–MS/NMR: A Fast Identification of Acetylcholinesterase Inhibitors from Galbanum†

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Product

Resources

About

Combination of Bioautography with HPTLC–MS/NMR: A Fast Identification of Acetylcholinesterase Inhibitors from Galbanum^†