Alkaloids from Chlidanthus fragrans and their Acetylcholinesterase, Butyrylcholinesterase and Prolyl Oligopeptidase Activities

Eleven Amaryllidaceae alkaloids (1–11) were isolated from fresh bulbs of Chlidanthus fragrans Herb. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic experiments. Complete NMR assignments were achieved for deoxypretazzetine (1). All compounds were evaluated for their erythrocytic acetylcholinesterase and serum butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro- p-nitroanilide was used as substrate. In biological assays, only the crinine type Amaryllidaceae alkaloid undulatine showed promising acetylcholinesterase and prolyl oligopeptidase inhibition activity with IC50 values of 23.0 ± 1.0 μM and 1.96 ± 0.12 mM, respectively. Other isolated compounds were considered inactive.

Download Full-text

Alkaloids from Peumus boldus and their Acetylcholinesterase, Butyrylcholinesterase and Prolyl Oligopeptidase Inhibition Activity

Natural Product Communications ◽

10.1177/1934578x1501000410 ◽

2015 ◽

Vol 10 (4) ◽

pp. 1934578X1501000 ◽

Cited By ~ 1

Author(s):

Anna Hošt'álková ◽

Lubomír Opletal ◽

Jiří Kuneš ◽

Zdeněk Novák ◽

Martina Hrabinová ◽

...

Keyword(s):

Spectroscopic Analysis ◽

2D Nmr ◽

Inhibition Activity ◽

Isoquinoline Alkaloids ◽

Prolyl Oligopeptidase ◽

Benzylisoquinoline Alkaloids ◽

Chemical Structures ◽

Chromatographic Methods ◽

Ellman’S Method ◽

Butyrylcholinesterase Inhibition

Eleven isoquinoline alkaloids (1–11) were isolated from dried leaves of Peumus boldus Mol. by standard chromatographic methods. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analysis, and by comparison with literature data. Compounds isolated in sufficient amount were evaluated for their acetylcholinesterase, and butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro- p-nitroanilide was used as substrate. Promising butyrylcholinesterase inhibition activities were demonstrated by two benzylisoquinoline alkaloids, reticuline (8) and N-methylcoclaurine (9), with IC50 values of 33.6 ± 3.0 μM and 15.0 ± 1.4 μM, respectively. Important prolyl oligopeptidase inhibition activities were shown by N-methyllaurotetanine (6) and sinoacutine (4) with IC50 values of 135.4 ± 23.2 μM and 143.1 ± 25.4 μM, respectively. Other tested compounds were considered inactive.

Download Full-text

Structure Elucidation and Cholinesterase Inhibition Activity of Two New Minor Amaryllidaceae Alkaloids

Molecules ◽

10.3390/molecules26051279 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1279

Author(s):

Jana Maříková ◽

Abdullah Al Mamun ◽

Latifah Al Shammari ◽

Jan Korábečný ◽

Tomáš Kučera ◽

...

Keyword(s):

Active Sites ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Cholinesterase Inhibition ◽

Inhibition Activity ◽

Amaryllidaceae Alkaloids ◽

Chemical Structures ◽

Ic50 Values ◽

Narcissus Pseudonarcissus ◽

Inhibition Potency

Two new minor Amaryllidaceae alkaloids were isolated from Hippeastrum × hybridum cv. Ferrari and Narcissus pseudonarcissus cv. Carlton. The chemical structures were identified by various spectroscopic (one- and two-dimensional (1D and 2D) NMR, circular dichroism (CD), high-resolution mass spectrometry (HRMS) and by comparison with literature data of similar compounds. Both isolated alkaloids were screened for their human acetylcholinesterase (hAChE) and butyrylcholinesterase (hBuChE) inhibition activity. One of the new compounds, a heterodimer alkaloid of narcikachnine-type, named narciabduliine (2), showed balanced inhibition potency for both studied enzymes, with IC50 values of 3.29 ± 0.73 µM for hAChE and 3.44 ± 0.02 µM for hBuChE. The accommodation of 2 into the active sites of respective enzymes was predicted using molecular modeling simulation.

Download Full-text

FLAVONOIDS AND TRITERPENOIDS FROM CALLISTEMON CITRINUS AND THEIR INHIBITORY EFFECT ON NO PRODUCTION IN LPS-STIMULATED RAW264.7 MACROPHAGES

Vietnam Journal of Science and Technology ◽

10.15625/0866-708x/54/2/6741 ◽

2016 ◽

Vol 54 (2) ◽

pp. 214 ◽

Cited By ~ 1

Author(s):

Nguyen Manh Cuong ◽

Pham Ngoc Khanh ◽

Ho Viet Duc ◽

Tran Thu Huong ◽

Youn-Chui Kim ◽

...

Keyword(s):

Nitric Oxide ◽

2D Nmr ◽

Inhibitory Effect ◽

Raw264.7 Cells ◽

No Production ◽

Inhibition Activity ◽

Chemical Structures ◽

Raw264.7 Macrophages ◽

Phytochemical Investigation ◽

Methoxy Flavone

Phytochemical investigation of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of 12 flavonoid and triterpenoid compounds, including one new flavonoid, callistine A (1) and six known flavonoids 6,7- dimethyl-5,7-dihydroxy-4’-methoxy flavone (2), astragalin (3), quercetin (4), catechin (5), eucalyptin (6), and 8-demethyleucalyptin (7), along with 5 triterpenoids, 3-β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), betulinic acid (10), diospyrolide (11) and ursolic acid (12). Their chemical structures were determined from the spectroscopic evidences counting 1D- and 2D-NMR and HR-MS data. All the isolated compounds were examined for their anti-inflammatory activity against LPS-activated NO production in macrophage RAW264.7 cells. Among them, quercetin (4) and 3β-hydroxy-urs-11-en-13(28)-olide (9) showed potential inhibition activity in nitric oxide (NO) production in RAW264.7 cells exposed to LPS.

Download Full-text

(+)-Chenabinol (Revised NMR Data) and Two New Alkaloids from Berberis vulgaris and their Biological Activity

Natural Product Communications ◽

10.1177/1934578x1501001015 ◽

2015 ◽

Vol 10 (10) ◽

pp. 1934578X1501001 ◽

Cited By ~ 1

Author(s):

Zdeněk Novák ◽

Anna Hošt'álková ◽

Lubomir Opletal ◽

Lucie Nováková ◽

Martina Hrabinová ◽

...

Keyword(s):

Biological Activity ◽

2D Nmr ◽

Root Bark ◽

Inhibition Activity ◽

Prolyl Oligopeptidase ◽

Berberis Vulgaris ◽

Chromatographic Methods ◽

Nmr Data ◽

Human Butyrylcholinesterase

A known alkaloid (+)-chenabinol (1) and two new secobisbenzylisoquinoline alkaloids were isolated by standard chromatographic methods from the root bark of Berberis vulgaris L. The structures of the new alkaloids, named berkristine (2) and verfilline (3), were established by spectroscopic (including 2D NMR), and HRMS (ESI) methods. The alkaloids were tested for their inhibition activity of human cholinesterases and prolyl oligopeptidase. Compound 1 inhibited human butyrylcholinesterase with an IC50 value of 44.8 ± 5.4 μM.

Download Full-text

Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

Molecules ◽

10.3390/molecules26041080 ◽

2021 ◽

Vol 26 (4) ◽

pp. 1080

Author(s):

Imran Khan ◽

Jing Peng ◽

Zhuangjie Fang ◽

Wei Liu ◽

Wenjun Zhang ◽

...

Keyword(s):

Secondary Metabolites ◽

Nuclear Overhauser Effect ◽

Inhibition Activity ◽

Tyrosinase Inhibition ◽

Bioactive Natural Products ◽

Chemical Structures ◽

Overhauser Effect ◽

Spectroscopic Analyses ◽

Potential Resource ◽

Nuclear Overhauser

The fungus strain SCSIO 40433 was isolated from an Arctic-derived glacier sediment sample and characterized as Tolypocladium cylindrosporum. A new compound, cylindromicin (1), and seven known secondary metabolites (2–8) were isolated from this strain. The chemical structures of these compounds were elucidated by comprehensive spectroscopic analyses. Cylindromicin (1) featured a 3,4-dihydro-2H-pyran skeleton. The absolute configuration of compound 1 was assigned via interpretation of key Nuclear Overhauser Effect Spectroscopy (NOESY) correlations and Electronic Circular Dichroism (ECD) calculation. Cylindromicin (1) exhibited significant tyrosinase inhibition activity. This study highlights Polar fungi as a potential resource for new bioactive natural products.

Download Full-text

Diterpenoid and phenolic contents of Sideritis hololeuca Boiss & Heldr. Apud Bentham with antioxidant and anticholinesterase activity

Zeitschrift für Naturforschung C ◽

10.1515/znc-2019-0161 ◽

2020 ◽

Vol 75 (5-6) ◽

pp. 161-169

Author(s):

Sema Carikci ◽

Ahmet C. Goren ◽

Turgut Kilic

Keyword(s):

Essential Oil ◽

Biological Activities ◽

Reducing Power ◽

Acetone Extract ◽

Inhibition Activity ◽

Phenolic Contents ◽

Chromatography Tandem Mass Spectrometry ◽

Liquid Chromatography Tandem Mass ◽

Main Component ◽

Butyrylcholinesterase Inhibition

AbstractThe objective of this study is to determine essential oil, diterpenoid and phenolic contents of Sideritis hololeuca along with their biological activities. Phytol was found to be the main component of the essential oil. Seven known kaurane diterpenoids, siderol (140 mg, 0.16%, w/w), 7-acetoxy sideroxol (15 mg, 0.02%, w/w), eubol (6 mg, 0.01%, w/w), eubotriol (5 mg, 0.03%, w/w), 7-epicandicandiol (3 mg, 0.02%, w/w), ent-7α-acetoxy-18-hydroxykaur-16-ene (5 mg, 0.01%, w/w) and linearol [by liquid chromatography-tandem mass spectrometry (LC-MS/MS)] were determined from the species. Moreover, vanillin (21 mg, 0.10%, w/w), which was not isolated from any Sideritis species earlier, was isolated from an acetone extract of S. hololeuca. Quantitative amounts of some phenolic compounds in n-hexane, dichloromethane, acetone, methanol extracts and infusion and decoction of the plants were also investigated by LC-MS/MS. Antioxidant capacity and acetylcholinesterase, butyrylcholinesterase inhibition effects of the species were evaluated. The extracts of methanol and infusion and decoction of species showed moderate butyrylcholinesterase inhibition activity. The highest inhibition was observed from the decoction of species. The Cu2+ reducing power of infusion was determined as 1.435 mmol TR g−1.

Download Full-text

Identification and Characterization of α-Glucosidase Inhibition Flavonol Glycosides from Jack Bean (Canavalia ensiformis (L.) DC

Molecules ◽

10.3390/molecules25112481 ◽

2020 ◽

Vol 25 (11) ◽

pp. 2481

Author(s):

Anita M. Sutedja ◽

Emiko Yanase ◽

Irmanida Batubara ◽

Dedi Fardiaz ◽

Hanifah N. Lioe

Keyword(s):

2D Nmr ◽

The Other ◽

Inhibition Activity ◽

Jack Bean ◽

Canavalia Ensiformis ◽

Kaempferol Glycosides ◽

Uv Visible ◽

First Time ◽

Identification And Characterization

Although the intake of jack bean (Canavalia ensiformis (L.) DC.), an underutilized tropical legume, can potentially decrease the risk of several chronic diseases, not much effort has been directed at profiling the polyphenolics contained therein. Hence, this work aimed to identify and quantify the dominant jack bean polyphenolics, which are believed to have antioxidant and other bioactivities. Four major compounds were detected and identified as kaempferol glycosides with three or four glycoside units. Their structures were established based on UV-visible, 1D, 2D NMR, and HR-ESI-MS analyses. Specifically, kaempferol 3-O-α-l-rhamnopyranosyl (1→6)- β-d-glucopyranosyl (1→2)-β-d-galactopyranosyl-7-O-[3-O-o-anisoyl]-α-l-rhamnopyranoside was detected for the first time, while the other three compounds have already been described in plants other than jack bean. This new compound was found to have a higher α-glucosidase inhibition activity compared to acarbose.

Download Full-text

Solution behavior and complete proton and carbon-13 NMR assignments of the coenzyme B12 derivative (5'-deoxyadenosyl)cobinamide using modern 2D NMR experiments, including 600 MHz proton NMR data

Journal of the American Chemical Society ◽

10.1021/ja00186a051 ◽

1989 ◽

Vol 111 (4) ◽

pp. 1484-1491 ◽

Cited By ~ 26

Author(s):

Thomas G. Pagano ◽

Paulos G. Yohannes ◽

Benjamin P. Hay ◽

Jerry R. Scott ◽

Richard G. Finke ◽

...

Keyword(s):

Nmr Assignments ◽

Proton Nmr ◽

2D Nmr ◽

Coenzyme B12 ◽

Solution Behavior ◽

Nmr Data

Download Full-text

Synthesis and bioactivity of novel C2-glycosyl triazole derivatives as acetylcholinesterase inhibitors

Heterocyclic Communications ◽

10.1515/hc-2016-0163 ◽

2017 ◽

Vol 23 (3) ◽

pp. 231-236 ◽

Cited By ~ 1

Author(s):

Long Yin ◽

Lei Wang ◽

Xiu-Jian Liu ◽

Feng-Chang Cheng ◽

Da-Hua Shi ◽

...

Keyword(s):

Aqueous Solution ◽

Sodium Hydroxide ◽

Acetylcholinesterase Inhibitors ◽

Acetylcholinesterase Inhibition ◽

Inhibition Activity ◽

Triazole Derivatives ◽

Inhibitory Activities ◽

Ellman’S Method

AbstractNew C2-glycosyl triazole derivatives 6a–l were synthesized by cyclization of glycosyl acylthiosemicarbazides 5 in refluxing 3 N sodium hydroxide aqueous solution. Substrates 5 were obtained by the reaction of glycosyl isothiocyanate 3 with various hydrazides. The acetylcholinesterase (AChE) inhibitory activities of compounds 6 were tested by Ellman’s method. Compounds that exhibited over 85% inhibition were subsequently evaluated for the IC50 values. Compound 6f possesses the best acetylcholinesterase-inhibition activity with IC50 of 1.46±0.25 μg/mL.

Download Full-text

Exploring the Phytochemicals of Acacia melanoxylon R. Br.

Plants ◽

10.3390/plants10122698 ◽

2021 ◽

Vol 10 (12) ◽

pp. 2698

Author(s):

Diana Alves ◽

Sidónio Duarte ◽

Pedro Arsénio ◽

Joana Gonçalves ◽

Cecília M. P. Rodrigues ◽

...

Keyword(s):

Colorectal Cancer ◽

Mass Spectrometry ◽

Methyl Ester ◽

Nmr Assignments ◽

2D Nmr ◽

Human Colorectal Cancer ◽

2D Nmr Spectroscopy ◽

Acacia Melanoxylon ◽

Colorectal Cancer Cells ◽

Human Colorectal Cancer Cells

Invasive species are currently a world menace to the environment, although the study of their chemistry may provide a means for their future beneficial use. From a study of Portuguese Acacia melanoxylon R. Br. five known compounds were isolated: lupeol, 3β-Z-coumaroyl lupeol, 3β-E-coumaroyl lupeol (dioslupecin A), kolavic acid 15-methyl ester and vomifoliol (blumenol A). Their structures were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry, and as a result some corrections are made to their previous 13C NMR assignments. Cytotoxicity of 3β-E-coumaroyl lupeol (dioslupecin A) and kolavic acid 15-methyl ester was evaluated against HCT116 human colorectal cancer cells although biological activity was not evident.

Download Full-text