α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies
Chemical investigation of Carthamus tinctorius L. flowers resulted in isolation of seven metabolites that were identified as; p-Hydroxybenzoic acid (1), trans hydroxy cinnamic acid (2), kaempferol-6-C-glucoside (3), astragalin (4), cartormin (5), kaempferol-3-O-rutinoside (6), and kaempferol–3-O-sop...
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| Format: | Article |
| Language: | English |
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Springer
2024-07-01
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| Series: | Saudi Pharmaceutical Journal |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319016424001567 |
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| author | Jawaher A.M. Alotaibi Alaa Sirwi Ali M. El-Halawany Ahmed Esmat Gamal A. Mohamed Sabrin R.M. Ibrahim Abdulrahim A. Alzain Taher F. Halawa Martin Safo Hossam M. Abdallah |
| author_facet | Jawaher A.M. Alotaibi Alaa Sirwi Ali M. El-Halawany Ahmed Esmat Gamal A. Mohamed Sabrin R.M. Ibrahim Abdulrahim A. Alzain Taher F. Halawa Martin Safo Hossam M. Abdallah |
| author_sort | Jawaher A.M. Alotaibi |
| collection | DOAJ |
| description | Chemical investigation of Carthamus tinctorius L. flowers resulted in isolation of seven metabolites that were identified as; p-Hydroxybenzoic acid (1), trans hydroxy cinnamic acid (2), kaempferol-6-C-glucoside (3), astragalin (4), cartormin (5), kaempferol-3-O-rutinoside (6), and kaempferol–3-O-sophoroside (7). Virtual screening of the isolated compounds against human intestinal α-glucosidase, acetylcholinesterase, and butyrylcholinesterase was carried out. Additionally, the antioxidant activity of the bioactive compounds was assessed. Compounds 1 and 5 exhibited moderate binding affinities to acetylcholinesterase (binding energy −5.33 and −4.18 kcal/mol, respectively), compared to donepezil (-83.33kcal/mol). Compounds 1–7 demonstrated weak affinity to butyrylcholinesterase. Compounds 2 and 4 displayed moderate binding affinity to human intestinal α-glucosidase,compared to Acarbose (reference compound), meanwhile compound 2 exhibited lower affinity. Molecular dynamic studies revealed that compound 4 formed a stable complex with the binding site throughout a 100 ns simulation period. The in-vitro results were consistent with the virtual experimental results, as compounds 1 and 5 showed mild inhibitory effects on acetylcholinesterase (IC50s 150.6 and 168.7 µM, respectively). Compound 4 exhibited moderate α-glucosidase inhibition with an IC50 of 93.71 µM. The bioactive compounds also demonstrated notable antioxidant activity in ABTS [2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)], ORAC (oxygen radical-absorbance capacity), and metal chelation assays, suggesting their potential in improving dementia in Alzheimer’s disease (AD) and mitigating hyperglycemia. |
| format | Article |
| id | doaj-art-1c09a1a2ecd746738969a02b87ff7145 |
| institution | Kabale University |
| issn | 1319-0164 |
| language | English |
| publishDate | 2024-07-01 |
| publisher | Springer |
| record_format | Article |
| series | Saudi Pharmaceutical Journal |
| spelling | doaj-art-1c09a1a2ecd746738969a02b87ff71452025-08-20T03:54:38ZengSpringerSaudi Pharmaceutical Journal1319-01642024-07-0132710210610.1016/j.jsps.2024.102106α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studiesJawaher A.M. Alotaibi0Alaa Sirwi1Ali M. El-Halawany2Ahmed Esmat3Gamal A. Mohamed4Sabrin R.M. Ibrahim5Abdulrahim A. Alzain6Taher F. Halawa7Martin Safo8Hossam M. Abdallah9Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Cairo University, Giza 11562, EgyptDepartment of Clinical Pharmacology, Faculty of Medicine, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaPreparatory Year Program, Department of Chemistry, Batterjee Medical College, Jeddah 21442, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, EgyptDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Gezira, Wad Madani 21111, SudanDepartment of Pediatrics, Aberdeen Hospital, Newglasgow, Nova Scotia Health Authorities, Nova Scotia, CanadaDepartment of Medicinal Chemistry, Center for Drug Discovery, School of Pharmacy, Virginia Commonwealth University, 800 East Leigh Street, Richmond, VA 23298, USADepartment of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia; Corresponding author.Chemical investigation of Carthamus tinctorius L. flowers resulted in isolation of seven metabolites that were identified as; p-Hydroxybenzoic acid (1), trans hydroxy cinnamic acid (2), kaempferol-6-C-glucoside (3), astragalin (4), cartormin (5), kaempferol-3-O-rutinoside (6), and kaempferol–3-O-sophoroside (7). Virtual screening of the isolated compounds against human intestinal α-glucosidase, acetylcholinesterase, and butyrylcholinesterase was carried out. Additionally, the antioxidant activity of the bioactive compounds was assessed. Compounds 1 and 5 exhibited moderate binding affinities to acetylcholinesterase (binding energy −5.33 and −4.18 kcal/mol, respectively), compared to donepezil (-83.33kcal/mol). Compounds 1–7 demonstrated weak affinity to butyrylcholinesterase. Compounds 2 and 4 displayed moderate binding affinity to human intestinal α-glucosidase,compared to Acarbose (reference compound), meanwhile compound 2 exhibited lower affinity. Molecular dynamic studies revealed that compound 4 formed a stable complex with the binding site throughout a 100 ns simulation period. The in-vitro results were consistent with the virtual experimental results, as compounds 1 and 5 showed mild inhibitory effects on acetylcholinesterase (IC50s 150.6 and 168.7 µM, respectively). Compound 4 exhibited moderate α-glucosidase inhibition with an IC50 of 93.71 µM. The bioactive compounds also demonstrated notable antioxidant activity in ABTS [2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)], ORAC (oxygen radical-absorbance capacity), and metal chelation assays, suggesting their potential in improving dementia in Alzheimer’s disease (AD) and mitigating hyperglycemia.http://www.sciencedirect.com/science/article/pii/S1319016424001567SafflowerFlavonoidsAlzheimerDiabetesIndustrial developmentAntioxidant |
| spellingShingle | Jawaher A.M. Alotaibi Alaa Sirwi Ali M. El-Halawany Ahmed Esmat Gamal A. Mohamed Sabrin R.M. Ibrahim Abdulrahim A. Alzain Taher F. Halawa Martin Safo Hossam M. Abdallah α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies Saudi Pharmaceutical Journal Safflower Flavonoids Alzheimer Diabetes Industrial development Antioxidant |
| title | α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies |
| title_full | α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies |
| title_fullStr | α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies |
| title_full_unstemmed | α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies |
| title_short | α-Glucosidase, butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from Carthamus tinctorius L. flowers: In silico and in vitro studies |
| title_sort | α glucosidase butyrylcholinesterase and acetylcholinesterase inhibitory activities of phenolic compounds from carthamus tinctorius l flowers in silico and in vitro studies |
| topic | Safflower Flavonoids Alzheimer Diabetes Industrial development Antioxidant |
| url | http://www.sciencedirect.com/science/article/pii/S1319016424001567 |
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