Smoke derived karrikinolide and trimethylbutenolide exerted neuroprotective effects against monoamine oxidase and acetylcholinesterase. Synthesis of potent analogs was achieved. Sulphur substitution in the bicyclic ring structure of KAR1 displayed the most encouraging activity returning IC50 values of 13.75 ± 0.001 μM and 0.03 ± 0.02 μM for monoamine oxidase A and B and 0.08 ± 0.006 μM for acetylcholinesterase. Neuroprotective butenolides may be particularly useful in the treatment of depressive disorders, Alzheimer's and Parkinson's diseases.
- MeSH
- acetylcholinesterasa metabolismus MeSH
- depresivní poruchy farmakoterapie MeSH
- furany chemická syntéza chemie farmakologie MeSH
- gama-butyrolakton analogy a deriváty chemická syntéza chemie farmakologie MeSH
- inhibitory MAO chemická syntéza chemie farmakologie MeSH
- lidé MeSH
- molekulární struktura MeSH
- monoaminoxidasa metabolismus MeSH
- neurodegenerativní nemoci farmakoterapie MeSH
- neuroprotektivní látky chemická syntéza chemie farmakologie MeSH
- pyrany chemická syntéza chemie farmakologie MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
Scadoxus puniceus (Amaryllidaceae), a medicinal plant of high value in South Africa, is used as a component of a traditional herbal tonic prescribed to treat several ailments. Ultra-high performance liquid chromatography-tandem mass spectrometry quantified the phenolic compounds in different organs of S. puniceus. Gravity column chromatography was used to separate fractions and active compounds. The structure of these compounds was determined using 1D and 2D nuclear magnetic resonance and mass spectroscopic techniques. A microplate technique was used to determine the acetylcholinesterase inhibitory activity of the pure compounds. Metabolite profiling revealed a greater profusion of hydroxycinnamic acids (69.5%), as opposed to hydroxybenzoic acids (30.5%). Chlorogenic acid was the most abundant (49.6% of hydroxycinnamic acids) compound. In addition to chlorogenic acid, the study is the first to report the presence of sinapic, gallic, and m-hydroxybenzoic acids in the Amaryllidaceae. Chromatographic separation of S. puniceus led to the isolation of haemanthamine (1), haemanthidine (2), and a rare chlorinated amide, metolachlor (3), the natural occurrence of which is described for the first time. Haemanthamine, haemanthidine, and metolachlor displayed strong acetylcholinesterase inhibitory activity (IC50 ; 23.1, 23.7, and 11.5 μM, respectively). These results substantiate the frequent use of S. puniceus as a medicinal plant and hold much promise for further pharmaceutical development.
- MeSH
- acetamidy chemie izolace a purifikace metabolismus farmakologie MeSH
- alkaloidy amarylkovitých chemie izolace a purifikace metabolismus farmakologie MeSH
- Amaryllidaceae chemie metabolismus MeSH
- cholinesterasové inhibitory chemie izolace a purifikace farmakologie MeSH
- fenantridiny chemie izolace a purifikace metabolismus farmakologie MeSH
- kyseliny kumarové chemie izolace a purifikace metabolismus farmakologie MeSH
- léčivé rostliny chemie MeSH
- rostlinné extrakty chemie izolace a purifikace metabolismus farmakologie MeSH
- tandemová hmotnostní spektrometrie MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Jihoafrická republika MeSH
