Cholinesterase inhibitory triterpenoids from the bark of Garcinia hombroniana.
Abstract: Context: Garcinia hombroniana Pierre, known as manggis hutan in Malaysia is a rich source of xanthones and benzophenones. Objective: This study was aimed to isolate and characterize potential cholinesterase inhibitors from the extracts of G. hombroniana bark and investigate their interactions with the enzymes. Methods: The dichloromethane extract afforded five triterpenoids which were characterized by NMR and mass spectral techniques. Cholinesterase inhibitory assay and molecular docking were performed to get insight of the inhibitory activity and molecular interactions of the compounds. The compounds were also tested for their antioxidant capacity. Results: The isolated triterpenoids were identified as: 2β-hydroxy-3α-O-caffeoyltaraxar-14-en-28-oic acid (1), taraxerol (2), taraxerone (3), betulin (4) and betulinic acid (5). Compound 1 was the most active dual inhibitor of both AChE and BChE. Compound 1 also showed good antioxidant activities. Conclusions: Compound 1 had dual and moderate inhibitory activity on AChE and BChE worthy for further investigations.
Publication Date: 2014-03-25 PubMed ID: 24666300DOI: 10.3109/14756366.2014.895720Google Scholar: Lookup
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- Journal Article
- Research Support
- Non-U.S. Gov't
Summary
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This study researched the potential for triterpenoids from the bark of the Malaysian plant Garcinia hombroniana to act as cholinesterase inhibitors. The most potent compound identified, referred to as Compound 1, also demonstrated antioxidant activity.
Study Objective and Methods
- The main objective of the study was to extract, isolate and identify potential cholinesterase inhibitors from the bark of Garcinia hombroniana, a tree native to Malaysia. Cholinesterase inhibitors slow the breakdown of acetylcholine, a neurotransmitter, in the brain and can be used in treatment of Alzheimer’s disease and other memory-related conditions.
- The researchers used the method of dichloromethane extraction to obtain five different triterpenoids, a class of chemical compounds.
- These compounds were identified and characterized using Nuclear Magnetic Resonance (NMR) and mass spectral techniques.
- Additional testing was conducted to understand their level of inhibitory activity and their specific interactions with enzymes. This process was done through a cholinesterase inhibitory assay and a molecular docking experiment.
- The antioxidant capacity of each of the compounds was also measured.
Results
- The five triterpenoids identified were: 2β-hydroxy-3α-O-caffeoyltaraxar-14-en-28-oic acid (Compound 1), taraxerol (Compound 2), taraxerone (Compound 3), betulin (Compound 4) and betulinic acid (Compound 5).
- Among these, Compound 1 had the most potent inhibitory effect on both types of cholinesterase – acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).
- Compound 1 also indicated good antioxidant activity.
Conclusions
- The researchers concluded that Compound 1 showed both dual cholinesterase inhibitory activity and antioxidant capacity.
- Given its moderate inhibitory effect on both AChE and BChE, it was suggested that Compound 1 is a promising candidate for further study and development in the treatment of memory-related disorders.
Cite This Article
APA
Jamila N, Khairí·ªn M, Yeong KK, Osman H, Murugaiyah V.
(2014).
Cholinesterase inhibitory triterpenoids from the bark of Garcinia hombroniana.
J Enzyme Inhib Med Chem, 30(1), 133-139.
https://doi.org/10.3109/14756366.2014.895720 Publication
Researcher Affiliations
- School of Chemical Sciences, Universiti Sains Malaysia , Penang , Malaysia and.
MeSH Terms
- Animals
- Antioxidants / chemistry
- Antioxidants / isolation & purification
- Butyrylcholinesterase / chemistry
- Cholinesterase Inhibitors / chemistry
- Cholinesterase Inhibitors / isolation & purification
- Cholinesterases / chemistry
- Electrophorus
- Garcinia / chemistry
- Horses
- Methylene Chloride
- Molecular Docking Simulation
- Plant Bark / chemistry
- Plant Extracts / chemistry
- Solvents
- Triterpenes / chemistry
- Triterpenes / isolation & purification
Citations
This article has been cited 13 times.- Smyrska-Wieleba N, Mroczek T. Natural Inhibitors of Cholinesterases: Chemistry, Structure-Activity and Methods of Their Analysis.. Int J Mol Sci 2023 Feb 1;24(3).
- Mus AA, Goh LPW, Marbawi H, Gansau JA. The Biosynthesis and Medicinal Properties of Taraxerol.. Biomedicines 2022 Mar 30;10(4).
- Lai Shi Min S, Liew SY, Chear NJY, Goh BH, Tan WN, Khaw KY. Plant Terpenoids as the Promising Source of Cholinesterase Inhibitors for Anti-AD Therapy.. Biology (Basel) 2022 Feb 14;11(2).
- Tamfu AN, Kucukaydin S, Yeskaliyeva B, Ozturk M, Dinica RM. Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources.. Molecules 2021 Sep 14;26(18).
- Uddin MJ, Russo D, Rahman MM, Uddin SB, Halim MA, Zidorn C, Milella L. Anticholinesterase Activity of Eight Medicinal Plant Species: In Vitro and In Silico Studies in the Search for Therapeutic Agents against Alzheimer's Disease.. Evid Based Complement Alternat Med 2021;2021:9995614.
- Kong CK, Low LE, Siew WS, Yap WH, Khaw KY, Ming LC, Mocan A, Goh BH, Goh PH. Biological Activities of Snowdrop (Galanthus spp., Family Amaryllidaceae).. Front Pharmacol 2020;11:552453.
- Salazar JR, Loza-Mejía MA, Soto-Cabrera D. Chemistry, Biological Activities and In Silico Bioprospection of Sterols and Triterpenes from Mexican Columnar Cactaceae.. Molecules 2020 Apr 3;25(7).
- Faraone I, Russo D, Chiummiento L, Fernandez E, Choudhary A, Monné M, Milella L, Rai DK. Phytochemicals of Minthostachys diffusa Epling and Their Health-Promoting Bioactivities.. Foods 2020 Feb 1;9(2).
- Loesche A, Kahnt M, Serbian I, Brandt W, Csuk R. Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase.. Molecules 2019 Mar 7;24(5).
- Sun Z, Wu Y, Liu S, Hu S, Zhao B, Li P, Du S. Effects of Panax Notoginseng Saponins on Esterases Responsible for Aspirin Hydrolysis In Vitro.. Int J Mol Sci 2018 Oct 12;19(10).
- Knežević A, Stajić M, Sofrenić I, Stanojković T, Milovanović I, Tešević V, Vukojević J. Antioxidative, antifungal, cytotoxic and antineurodegenerative activity of selected Trametes species from Serbia.. PLoS One 2018;13(8):e0203064.
- Jamila N, Khan N, Khan AA, Khan I, Khan SN, Zakaria ZA, Khairí·ªn M, Osman H, Kim KS. IN VIVO CARBON TETRACHLORIDE-INDUCED HEPATOPROTECTIVE AND IN VITRO CYTOTOXIC ACTIVITIES OF GARCINIA HOMBRONIANA (SEASHORE MANGOSTEEN).. Afr J Tradit Complement Altern Med 2017;14(2):374-382.
- Locatelli M, Zengin G, Uysal A, Carradori S, De Luca E, Bellagamba G, Aktumsek A, Lazarova I. Multicomponent pattern and biological activities of seven Asphodeline taxa: potential sources of natural-functional ingredients for bioactive formulations.. J Enzyme Inhib Med Chem 2017 Dec;32(1):60-67.
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