New diterpenoids isolated from Leonurus japonicus and their acetylcholinesterase inhibitory activity

Wu, Hongyi; Sun, Ting; Zhao, Feng; Zhang, Liping; Li, Gang; Zhang, Jie

doi:10.1016/s1875-5364(18)30020-7

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…Acetylcholinesterase (AChE) is a major functional enzyme that hydrolyzes acetylcholine (ACh) in the central nervous system. Anatomical studies have found that AChE protein expression in the brain of Alzheimer’s disease (AD) patients is elevated [19,20]. In recent years, there have been more and more studies on acetylcholinesterase inhibitors [21].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Guo

Zhang

et al. 2019

Molecules

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Bee pollen contains all the essential amino acids needed by humans. China is the largest producer of bee pollen in the world. In the present study, we identified 11 fatty acids in F. esculentum bee pollen oil by GC-MS analysis, and 16 compounds were isolated from F. esculentum bee pollen by column chromatography and identified. A high-performance liquid chromatography-diode array detector (HPLC-DAD) method was established for the quality control of F. esculentum bee pollen. A validated HPLC-DAD method was successfully applied to the simultaneous characterization and quantification of nine main constituents in seven samples collected from seven different areas in China. The results showed that all standard calibration curves exhibited good linearity (R2 > 0.999) in HPLC-DAD analysis with excellent precision, repeatability and stability. The total amount in the samples from the seven regions ranged from 23.50 to 46.05 mg/g. In addition, seven compounds were studied for their bioactivity using enzymic methods, whereby kaempferol (3) showed high α-glucosidase inhibitory activity (IC50: 80.35 μg/mL), ergosterol peroxide (8) showed high tyrosinase inhibitory activity (IC50: 202.37 μg/mL), and luteolin (1) had strong acetylcholinesterase inhibitory activity (IC50: 476.25 μg/mL). All results indicated that F. esculentum bee pollen could be a nutritious health food.

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Section: Introductionmentioning

confidence: 99%

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Guo

Zhang

et al. 2019

Molecules

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“…To the best of our knowledge, this is the first phytochemical investigation on potential anti-cholinesterase candidates from F. dentatoalata . However, several compounds already have been evaluated for their potential anti-cholinesterase effects before, especially flavonoids ( Wu et al, 2017 ; Borowiec et al, 2022 ). For examples, compounds 1 , 5 and 19 showed over 50% inhibitions against AChE and BuChE, which further proved to be comparable with reported values ( Kim et al, 2016 ; Nugroho et al, 2018 ; Islam et al, 2021 ; Karatas et al, 2022 ).…”

Section: Discussionmentioning

confidence: 99%

In Vitro and in Silico Analysis of Phytochemicals From Fallopia dentatoalata as Dual Functional Cholinesterase Inhibitors for the Treatment of Alzheimer’s Disease

et al. 2022

Front. Pharmacol.

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Current studies have found that butyrylcholinesterase (BuChE) replaces the biological function of acetylcholinesterase (AChE) in the late stage of Alzheimer’s disease. Species in the genus of Fallopia, rich in polyphenols with diverse chemical structures and significant biological activities, are considered as an important resource for screening natural products to against AD. In this study, thirty-four compounds (1–34) were isolated from Fallopia dentatoalata (Fr. Schm.) Holub, and their inhibitory effects against AChE and BuChE were assessed. Compounds of the phenylpropanoid sucrose ester class emerged as the most promising members of the group, with 31–33 displaying moderate AChE inhibition (IC50 values ranging from 30.6 ± 4.7 to 56.0 ± 2.4 µM) and 30–34 showing potential inhibitory effects against BuChE (IC50 values ranging from 2.7 ± 1.7 to 17.1 ± 3.4 µM). Tacrine was used as a positive control (IC50: 126.7 ± 1.1 in AChE and 5.5 ± 1.7 nM in BuChE). Kinetic analysis highlighted compounds 31 and 32 as non-competitive inhibitors of AChE with Ki values of ∼30.0 and ∼34.4 µM, whilst 30–34 were revealed to competitively inhibit BuChE with Ki values ranging from ∼1.8 to ∼17.5 µM. Molecular binding studies demonstrated that 30–34 bound to the catalytic sites of BuChE with negative binding energies. The strong agreement between both in vitro and in silico studies highlights the phenylpropanoid sucrose esters 30–34 as promising candidates for use in future anti-cholinesterase therapeutics against Alzheimer’s disease.

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“…[ 8 ] Diterpenoids have become widely studied in recent years. Modern pharmacological studies have revealed extensive pharmacological activity of diterpenoids of L. japonicus , which include antiplatelet aggregation, [ 9 ] immunomodulation, [ 10 ] anti‐inflammation, [ 11,12 ] neuroprotection, [ 13 ] α‐glucosidase inhibition, [ 14 ] acetylcholinesterase inhibition [ 15 ] and cytotoxicity against Hela cancer cells. [ 16 ] Nevertheless, the biological activity of the diterpenoids have not yet been investigated in tumour‐bearing animal models.…”

Section: Introductionmentioning

confidence: 99%

Immunomodulatory and antitumour bioactive labdane diterpenoids from Leonurus japonicus†

Yue

Liang

et al. 2020

Journal of Pharmacy and Pharmacology

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Objectives Two labdane diterpenoids, leojapone B and heteronone B, were isolated from Leonurus japonicus Houtt., and their biological activity were evaluated in this study. Methods Human and mouse cancer cells, human peripheral blood mononuclear cells (PBMCs) and mouse macrophages (RAW264.7 cells) were used to evaluate the activity of leojapone B and heteronone B, while the in vivo effects of leojapone B were further examined in Lewis Lung Cancer tumour-bearing mice. Key findings In vitro studies showed that leojapone B selectively inhibited the proliferation of lung cancer cells, and both leojapone B and heteronone B inhibited the production of pro-inflammatory cytokines in activated PBMCs. In tumour-bearing mice model, lung tumours were reduced in size in mice treated with intraperitoneal injections of leojapone B at 20 and 30 mg/kg for 14 days. The population ratio of CD4 + /CD8 + T cells in mouse spleens was found to be increased, while regulatory T cells were decreased after leojapone B treatment. Conclusions The inhibitory effects of leojapone B in mouse lung tumours were demonstrated for the first time in this study. The immunomodulatory activity of heteronone B were also demonstrated. Our findings indicated that both leojapone B and heteronone B may act as active components in L. japonicus.

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New diterpenoids isolated from Leonurus japonicus and their acetylcholinesterase inhibitory activity

Cited by 5 publications

References 28 publications

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

In Vitro and in Silico Analysis of Phytochemicals From Fallopia dentatoalata as Dual Functional Cholinesterase Inhibitors for the Treatment of Alzheimer’s Disease

Immunomodulatory and antitumour bioactive labdane diterpenoids from Leonurus japonicus†

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