Cholinesterase inhibitory alkaloids from the rhizomes of Coptis chinensis

Cao, Thao Quyen; Ngo, Quynh-Mai Thi; Seong, Su Hui; Youn, Ui Joung; Kim, Jeong Ah; Kim, Junheon; Kim, Jin-Cheol; Woo, Mi Hee; Choi, Jae Sue; Min, Byung Sun

doi:10.1016/j.bioorg.2018.01.038

Cited by 16 publications

(8 citation statements)

References 36 publications

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Section: Inhibition Of Cholinesterase Activitiessupporting

confidence: 76%

“…Cholinesterase inhibitors such as donepezil and galantamine have been successfully marketed as clinical agents to alleviate the symptoms of Alzheimer's disease. Berberine, a natural product with cholinesterase inhibitory activity, is often used as a positive control in the determination of cholinesterase inhibitory activity of natural products [50][51][52]. In the cholinesterase inhibition assay of MBE (Figure 3B,C), both MBE and berberine showed the concentrationdependent inhibition activity of AChE and BChE, but the inhibition activity of berberine against AChE was significantly better than that against BChE, as reported in previous In the previous study on α-glucosidase inhibitory components in mulberry (Morus alba L.) with molecular docking, three types of potential small-molecule α-glucosidase inhibitory components were identified: alkaloids (1-deoxynojirimycin, DNJ), flavonols (kaempferol, quercetin and rutin), and isoprenoid flavonoids (morin, sanggenon C and kuwanon G) [48].…”

Section: Inhibition Of Cholinesterase Activitiesmentioning

confidence: 99%

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UPLC-MS/MS Profiling, Antioxidant, α-Glucosidase Inhibitory, Cholinesterase Inhibitory, and Cardiovascular Protection Potentials of Jialing 20 (Morus multicaulis Perr.) Mulberry Branch Extract

Xiang

Xia

2021

Foods

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As a by-product in the sericulture industry, mulberry branches are not currently utilized effectively. Jialing 20 is an artificial triploids mulberry that widely cultivated in southwest China. In this study, the chemical composition of the Jialing 20 mulberry branch extract (MBE) was first analyzed by UPLC-MS/MS, and 42 components, including alkaloids, flavonoids, and coumarins, were obtained. Then, the antioxidant activities, hypoglycemic effect, Alzheimer’s disease inhibition, and cardiovascular protection of MBE were also evaluated in vitro. The IC50 values for the scavenging DPPH and ABTS radicals were, respectively, 31.23 ± 0.57 μg/mL and 8.88 ± 0.36 μg/mL (IC50 values of positive Vc were, respectively, 4.41 ± 0.19 μg/mL and 8.79 ± 0.41 μg/mL). The IC50 value for inhibiting α-glucosidase was 1.90 ± 0.05 μg/mL (IC50 value of positive acarbose was 0.03 μg/mL). The IC50 values for inhibiting acetylcholinesterase and butyrylcholinesterase were, respectively, 179.47 ± 0.38 μg/mL and 101.82 ± 3.37 μg/mL (IC50 values of positive berberine were, respectively, 1.27 ± 0.03 μg/mL and 57.41 ± 0.21 μg/mL). MBE (10 μg/mL and 40 μg/mL) significantly increased the survival rate of oxidized low-density lipoprotein- (ox-LDL) induced human umbilical vein endothelial cells (HUVECs) and significantly decreased the intracellular reactive oxygen species. These results suggest that the extracts of Jialing 20 mulberry branches could be used as a functional food additive.

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Section: Inhibition Of Cholinesterase Activitiessupporting

confidence: 76%

Section: Inhibition Of Cholinesterase Activitiesmentioning

confidence: 99%

UPLC-MS/MS Profiling, Antioxidant, α-Glucosidase Inhibitory, Cholinesterase Inhibitory, and Cardiovascular Protection Potentials of Jialing 20 (Morus multicaulis Perr.) Mulberry Branch Extract

Xiang

Xia

2021

Foods

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“…Recent studies on BBR mainly focus on its multitarget potential in neurodegenerative diseases, and BBR affected the biological functions of cholinesterase and monoamine oxidase, as well as the aggregation of amyloid-β (Aβ) associated with AD. − Previous studies have shown that patients with AD have a higher risk of developing T2DM. , The two disease-related proteins Aβ and hIAPP are structurally similar and have a coaggregation behavior, so they are frequently studied together to obtain high-quality dual inhibitors, such as flavonoids and artemisinins. , In addition, BBR is a major hypoglycemic component of Coptis chinensis alkaloids, which can promote the repair of islet β cells and improve the utilization of glucose by liver cells. The hypoglycemic effects of BBR on diabetic mice and patients have been confirmed. , Jatrorrhizine (JAT) is a metabolite of BBR with the same tetracyclic skeleton, and it can be obtained by opening the oxygen-containing five-membered ring at the end of BBR. The terminal hydroxyl modification increases the polarity of JAT, which may be related to the physiological activity of BBR in vivo. , JAT is also a predominant hypoglycemic ingredient from Rhizoma coptidis, which can specifically bind to α-glucosidase .…”

Section: Introductionmentioning

confidence: 98%

“…The hypoglycemic effects of BBR on diabetic mice and patients have been confirmed. 45,46 Jatrorrhizine (JAT) is a metabolite of BBR with the same tetracyclic skeleton, and it can be obtained by opening the oxygen-containing five-membered ring at the end of BBR. The terminal hydroxyl modification increases the polarity of JAT, which may be related to the physiological activity of BBR in vivo.…”

Section: ■ Introductionmentioning

confidence: 99%

Exploration of Isoquinoline Alkaloids as Potential Inhibitors against Human Islet Amyloid Polypeptide

Wang

Zheng

Huo

et al. 2022

ACS Chem. Neurosci.

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Type-2 diabetes mellitus (T2DM) is one of the most concerning public health problems because of its high incidence, multiple complications, and difficult treatment. Human islet amyloid polypeptide (hIAPP) is closely linked to T2DM because its abnormal self-assembly causes membrane damage and cell dysfunction. The development of potential inhibitors to prevent hIAPP fibrillation is a promising strategy for the intervention and treatment of diabetes. Natural isoquinoline alkaloids are used as effective medication that targets different biomolecules. Although studies explored the efficacy of berberine, jatrorrhizine, and chelerythrine in diabetes, the underlying mechanism remains unclear. Herein, three isoquinoline alkaloids are selected to reveal their roles in hIAPP aggregation, disaggregation, and cell protection. All three compounds displayed good inhibitory effects on peptide fibrillation, scattered the preformed fibrils into small oligomers and most monomers, and upregulated cell viability by reducing hIAPP oligomerization. Moreover, combined biophysical analyses indicated that the compounds affected the β-sheet structure and hydrophobicity of polypeptides significantly, and the benzo[c]phenanthridine structure of chelerythrine was beneficial to the inhibition of hIAPP aggregation and their hydrophobic interaction, compared with that of berberine and jatrorrhizine. Our work elaborated the effects of these alkaloids on hIAPP fibrillation and reveals a possible mechanism for these compounds against T2DM.

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“…The root and rhizome material of the Coptis species Rhizoma Coptidis (RC) is a top-grade drug that has been documented to have an excellent effect on improving memory and treating brain diseases in ancient clinical experience in China. Modern pharmacological studies have proven that this drug has a positive therapeutic potential on Alzheimer’s disease, and several alkaloids have been identified as the main AChE inhibitors ( Zhao et al., 2016 ; Cao et al., 2018 ; Lin et al., 2020a ). However, these studies mainly focused on the extract of RCdrugs from C. chinensis Franch, and other species of the Coptis genus have never been investigated regarding their anti-AChE properties.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the anti-AChE potential and alkaloids in Rhizoma Coptidis from different Coptis species combined with spectrum-effect relationship and molecular docking

Zhong²,

Liu³

et al. 2022

Front. Plant Sci.

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Coptis species are the main source of Rhizoma Coptidis (RC) drugs, which have always been used to treat Alzheimer’s disease in the clinical experience of ancient China. However, many species of this genus have been largely underutilized until now. With this fact, this research has been designed to investigate for the first time the anti-acetylcholinesterase (AChE) property of different extracts for RC drugs from four Coptis species (C. chinensis, C. deltoidea, C. teeta and C. omeiensis) and to quantify the main alkaloids. Petroleum ether, ethyl acetate and n-butanol fractions of RC drugs were sequentially collected using an accelerated solvent extraction technique. Spectrum-effect relationship and molecular docking were applied to analyse the relationships between alkaloids and AChE inhibitory activity. The N-butanol extract was proven to be the main active fraction, and C. teeta may be the best source of RC drugs for Alzheimer’s disease treatment, with significantly lower IC 20, IC 50 and IC 80 values for AChE inhibition. The UPLC/QqQ-MS quantitative analysis showed that the accumulations of 10 alkaloids in RC drugs from different sources greatly varied. Three data processing methods (Random forest, Boruta and Pearson correlation) comprehensively analysed the spectrum-effect relationship and revealed that columbamine, berberine and palmatine were the most important AChE inhibitors that could be used as quality markers to select RC drugs for Alzheimer’s disease treatment. In addition, the dominant compounds were successfully docked against AChE to verify the binding affinity and interactions with the active site. The present study can contribute to the reasonable development and utilization of RC drugs from different sources, especially to provide certain evidence for their application in the treatment of Alzheimer’s disease.

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Cholinesterase inhibitory alkaloids from the rhizomes of Coptis chinensis

Cited by 16 publications

References 36 publications

UPLC-MS/MS Profiling, Antioxidant, α-Glucosidase Inhibitory, Cholinesterase Inhibitory, and Cardiovascular Protection Potentials of Jialing 20 (Morus multicaulis Perr.) Mulberry Branch Extract

UPLC-MS/MS Profiling, Antioxidant, α-Glucosidase Inhibitory, Cholinesterase Inhibitory, and Cardiovascular Protection Potentials of Jialing 20 (Morus multicaulis Perr.) Mulberry Branch Extract

Exploration of Isoquinoline Alkaloids as Potential Inhibitors against Human Islet Amyloid Polypeptide

Characterization of the anti-AChE potential and alkaloids in Rhizoma Coptidis from different Coptis species combined with spectrum-effect relationship and molecular docking

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