Cholinesterase inhibitory potential of Dillenia suffruticosa chemical constituents and protective effect against Aβ−induced toxicity in transgenic Caenorhabditis elegans model

Abubakar, Saifullah; Khor, Boon‐Keat; Khaw, Kooi Yeong; Murugaiyah, Vikneswaran; Chan, Kit‐Lam

doi:10.1016/j.phyplu.2021.100022

Cited by 6 publications

(6 citation statements)

References 53 publications

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“…The three tested compounds in the in vitro assay exhibited interactions with Tyr 337, whose role in AChE is to maintain the electrostatic balance and the geometry of the binding gorge in the anionic catalytic site of this enzyme. [54] The observed interactions for phorate sulfoxide (23) were with Tyr 337, and Ser 203 as expected, since the organophosphate insecticides interact with serine residues [53] (Figure 2D).…”

Section: Molecular Dockingsupporting

confidence: 71%

“…In contrast, different interactions of betulinic acid (11) with the AChE from T. californica have been reported, due to the different origin of the enzyme. [53] On the other hand, the carboxylic acid of origanal (21) showed interactions with Phe 338 and there is a hydrogen bond interaction between Tyr 337 and the oxygen of the aldehyde at C-30 (Figure 2B). Scopoletin (20) showed hydrogen bond interactions with Arg 296 and Phe 295, π-π T-shaped interactions with Phe 297, π-π stacked interactions with Tyr 341, π-alkyl interactions with Tyr 337, and finally, van der Waals interactions with Tyr 124, Trp 286 and Ser 293 (Figure 2C).…”

Section: Molecular Dockingmentioning

confidence: 99%

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Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Pérez‐Valera,

Torres‐Martínez,

Nieto‐Camacho

et al. 2024

Chemistry & Biodiversity

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This report informs for the first time the chemical constituents of Diospyros xolocotzii and Diospyros digyna, the pesticidal and the acetylcholinesterase (AChE) inhibition potential of some compounds calculated by in silico approaches, the larvicidal activity against Spodoptera frugiperda of available compounds, the AChE inhibition of selected compounds, and the results of the molecular docking of the most active ones with this receptor. From the aerial parts of D.xolocotzii were isolated pentacyclic triterpenes (1‐4, 6, 10, 11‐13), phytosterols (15‐17), and isodiospyrin (18), whereas the analysis of aerial parts of D. digyna conducted to the isolation of pentacyclic triterpenes (4, 5, 7‐9, 11‐14), (4S)‐shinanolone (19), and scopoletin (20). For comparison purposes, origanal (21) was chemically prepared from 11. The in silico analysis showed that the tested compounds have pesticide potential. The larvicidal activities of 11 > 13 > 12 indicated that the increase of the oxidation degree at C‐28 increases their bioactivity. Compounds 11 and 21 presented the higher inhibition in the acetylcholinesterase assay, and the higher binding energies, and interactions with AChE by molecular docking. Both Diospyros species are sources of triterpenes with pesticidal potential and the molecular changes in lupane triterpenes correlate with the observed bioactivity and molecular docking.

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Section: Molecular Dockingsupporting

confidence: 71%

Section: Molecular Dockingmentioning

confidence: 99%

Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Pérez‐Valera,

Torres‐Martínez,

Nieto‐Camacho

et al. 2024

Chemistry & Biodiversity

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“…Analysis revealed three triterpenoids and three flavonoids in Dillenia suffruticosa leaves, and among those six phytoconstituents, betulinic acid, koetjapic acid, and kaempferol had the highest inhibition activity against AChE and BChE, whereas the others showed relatively low potency in Caenorhabditis elegans [ 30 ]. In addition to AChE inhibition, antioxidant potential of Rosmarinus officinalis was reported withIC 50 values of 272 µg/mL, 387 µg/mL, and 534 µg/mL for ethyl-acetate, ethanol, and aqueous extracts, respectively [ 31 ].…”

Section: Plants and Their Bioactive Compounds In Averting The Pathoge...mentioning

confidence: 99%

Plant-Derived Bioactive Compounds in the Management of Neurodegenerative Disorders: Challenges, Future Directions and Molecular Mechanisms Involved in Neuroprotection

et al. 2023

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Neurodegenerative disorders encompass a wide range of pathological conditions caused by progressive damage to the neuronal cells and nervous-system connections, which primarily target neuronal dysfunction and result in problems with mobility, cognition, coordination, sensation, and strength. Molecular insights have revealed that stress-related biochemical alterations such as abnormal protein aggregation, extensive generation of reactive oxygen and nitrogen species, mitochondrial dysfunction, and neuroinflammation may lead to damage to neuronal cells. Currently, no neurodegenerative disease is curable, and the available standard therapies can only provide symptomatic treatment and delay the progression of the disease. Interestingly, plant-derived bioactive compounds have drawn considerable attention due to their well-established medicinal properties, including anti-apoptotic, antioxidant, anti-inflammatory, anticancer, and antimicrobial properties, as well as neuroprotective, hepatoprotective, cardioprotective, and other health benefits. Plant-derived bioactive compounds have received far more attention in recent decades than synthetic bioactive compounds in the treatment of many diseases, including neurodegeneration. By selecting suitable plant-derived bioactive compounds and/or plant formulations, we can fine tune the standard therapies because the therapeutic efficacy of the drugs is greatly enhanced by combinations. A plethora of in vitro and in vivo studies have demonstrated plant-derived bioactive compounds’ immense potential, as proven by their capacity to influence the expression and activity of numerous proteins implicated in oxidative stress, neuroinflammation, apoptosis, and aggregation. Thus, this review mostly focuses on the antioxidant, anti-inflammatory, anti-aggregation, anti-cholinesterase, and anti-apoptotic properties of several plant formulations and plant-derived bioactive compounds and their molecular mechanisms against neurodegenerative disorders.

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“…Currently, there is no definite cure for AD, and most available drugs approved by FDA, such as donepezil, galantamine, and rivastigmine, are ChE inhibitors that improve cognitive disorders and the disease symptoms [18]. In this respect, development of ChE inhibitors is still in demand and it should be noted that selective anti-AChE activity can be achieved by small molecules, while selective anti-BChE activity is possible by bulky ligands since BChE has displayed low substrate specificity [19]. Another point that highlights the importance of the inhibition of ChEs is their noncholinergic role especially that of BChE in the deposition of βA plaques [20].…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Analysis and Evaluation of Biological Activity of Lawsonia inermis Seeds Related to Alzheimer’s Disease

Balaei-Kahnamoei

Saeedi

Rastegari

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Using Lawsonia inermis L. (henna) seeds has been frequently recommended for the improvement of memory in Iranian Traditional Medicine (ITM). In this respect, different fractions of the plant were prepared and evaluated for their in vitro biological assays related to Alzheimer’s disease (AD), including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity as well as metal chelating ability and DPPH antioxidant activity. The dichloromethane and ethyl acetate fractions were able to inhibit the BChE selectively with IC50 values of 113.47 and 124.90 μg/mL, respectively, compared with donepezil as the reference drug (IC50 = 1.52 μg/mL). However, all fractions were inactive toward AChE. Phytochemical analysis of the dichloromethane fraction indicated the presence of β-sitosterol (1), 3-O-β-acetyloleanolic acid (2), 3-O-(Z)-coumaroyl oleanolic acid (3), betulinic acid (4), and oleanolic acid (5). The inhibitory activity of isolated compounds was also evaluated toward AChE and BChE. Among them, compounds 2 and 5 showed potent inhibitory activity toward BChE with IC50 values of 77.13 and 72.20 μM, respectively. However, all compounds were inactive toward AChE. Moreover, molecular docking study confirmed desired interactions between those compounds and the BChE active site. The ability of fractions and compounds to chelate biometals (Cu2+, Fe2+, and Zn2+) was also investigated. Finally, DPPH antioxidant assay revealed that the ethyl acetate (IC50 = 3.08 μg/mL) and methanol (IC50 = 3.64 μg/mL) fractions possessed excellent antioxidant activity in comparison to BHA as the positive control (IC50 = 3.79 μg/mL).

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Cholinesterase inhibitory potential of Dillenia suffruticosa chemical constituents and protective effect against Aβ−induced toxicity in transgenic Caenorhabditis elegans model

Cited by 6 publications

References 53 publications

Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Plant-Derived Bioactive Compounds in the Management of Neurodegenerative Disorders: Challenges, Future Directions and Molecular Mechanisms Involved in Neuroprotection

Phytochemical Analysis and Evaluation of Biological Activity of Lawsonia inermis Seeds Related to Alzheimer’s Disease

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