Isoliensinine: A Natural Compound with “Drug-Like” Potential

Cheng, Yan; Li, Hongli; Zhou, Ziwei; Long, Hui-Zhi; Luo, Hongyu; Wen, Dan-Dan; Cheng, Lin; Gao, Lichen

doi:10.3389/fphar.2021.630385

Cited by 20 publications

(9 citation statements)

References 73 publications

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“…Beyond a regulation of synaptic acetylcholine levels, BChE also plays an important role in neurodegenerative disease progression [ 51 , 71 ]. With respect to the BChE inhibition, the bisbenzylisoquinoline [ 11 , 72 , 73 ] and protoberberine [ 74 , 75 ] alkaloids are usually more potent inhibitors of BChE than AChE. This fact is in a good agreement with the Gibbs free energies of binding in protein–ligand complexes found here by MD simulations for 1 and 3 .…”

Section: Resultssupporting

confidence: 87%

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

et al. 2022

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Alkaloids are natural products known as ethnobotanicals that have attracted increasing attention due to a wide range of their pharmacological properties. In this study, cholinesterase inhibitors were obtained from branches of Abuta panurensis Eichler (Menispermaceae), an endemic species from the Amazonian rainforest. Five alkaloids were isolated, and their structure was elucidated by a combination of 1D and 2D 1H and 13C NMR spectroscopy, HPLC-MS, and high-resolution MS: Lindoldhamine isomer m/z 569.2674 (1), stepharine m/z 298.1461 (2), palmatine m/z 352.1616 (3), 5-N-methylmaytenine m/z 420.2669 (4) and the N-trans-feruloyltyramine m/z 314.1404 (5). The compounds 1, 3, and 5 were isolated from A. panurensis for the first time. Interaction of the above-mentioned alkaloids with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes was investigated in silico by molecular docking and molecular dynamics. The molecules under investigation were able to bind effectively with the active sites of the AChE and BChE enzymes. The compounds 1–4 demonstrated in vitro an inhibitory effect on acetylcholinesterase with IC50 values in the range of 19.55 µM to 61.24 µM. The data obtained in silico corroborate the results of AChE enzyme inhibition.

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Section: Resultssupporting

confidence: 87%

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

et al. 2022

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“…Iso is one kind of bibenzyl isoquinoline alkaloid with antioxidant, anti-inflammatory, and anti-cancer activities (Cheng et al, 2021). In this study, Iso dysregulates osteoclast differentiation by mediating the NF-κB pathway, not the MAPK pathway.…”

Section: Discussionmentioning

confidence: 75%

“…Isoliensinine (Iso) is a dibenzyl isoquinoline alkaloid isolated from lotus seed embryos with antioxidant, antiinflammatory, and anti-cancer activities (Cheng et al, 2021). Research evidence has shown that Iso may stimulate the apoptosis of hepatoma cells by suppressing the activity of NF-κB as well as the p65 and phosphorylation (Shu et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Isoliensinine Suppresses Osteoclast Formation Through NF-κB Signaling Pathways and Relieves Ovariectomy-Induced Bone Loss

Liu

Huang

et al. 2022

Front. Pharmacol.

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Osteoporosis is among the major contributors of pathologic fracture in postmenopausal women, which is caused by the bone metabolic disorder owing to the over-activation of osteoclasts. Inhibition of osteoclast differentiation and maturation has become a mainstream research interest in the prevention of osteoporosis. Isoliensinine (Iso) is a dibenzyl isoquinoline alkaloid with antioxidant, anti-inflammatory, and anti-cancer activities. However, whether it can be used as a potential treatment for osteoporosis remains undiscovered. Here, we investigated whether Iso might suppress the differentiation of osteoclasts in vitro and in vivo to play an anti-osteoporosis role. Our results showed that Iso inhibits the formation of mature multinuclear osteoclasts induced by RANKL, the bone resorption, and the osteoclast-specific genes expression by blocking the nuclear translocation of NF-κB p65, and the effect was in a dosage-dependent way. Furthermore, we investigated the therapeutic effect of Iso on osteoporosis in ovariectomized (OVX) mice. We found that Iso attenuated bone loss in the OVX mice and significantly promoted BS, Conn. DN, Tb.Th, TB.N, and BV/TV Index. All in all, Iso showed a prominent effect of osteoclast inhibition, with great promise for treating osteoporosis.

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“…The in silico absorption, distribution, metabolism, excretion (ADME), and toxicity modeling is an important tool for rational drug design for studying interactions of ligands with biological targets at the atomic scale. As shown by the in silico results, the evaluated compounds, including vismione D, presented good predictive values with high gut absorption, as well as accordance to the Lipinski’s rule, an important characteristic for drug-likeness [ 32 , 33 ].…”

Section: Discussionmentioning

confidence: 99%

The Anti-Virulence Effect of Vismia guianensis against Candida albicans and Candida glabrata

et al. 2022

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In folk medicine, Vismia guianensis is used to treat skin diseases and mycoses in the Amazon region. We evaluated the anti-Candida activity of the hydroalcoholic extract from the leaves of Vismia guianensis (EHVG). HPLC-PDA and FIA-ESI-IT-MSn were used to chemically characterize EHVG. The anti-Candida activity was determined in vitro by the minimum inhibitory concentrations (MIC) against Candida glabrata (ATCC-2001); Candida albicans (ATCC-90028, ATCC-14053, and ATCC-SC5314), and C. albicans clinical isolates. EHVG effects on adhesion, growth, and biofilm formation were also determined. Molecular docking was used to predict targets for EHVG compounds. The main compounds identified included anthraquinone, vismione D, kaempferol, quercetin, and vitexin. EHVG was fungicidal against all tested strains. C. albicans ATCC 14053 and C. glabrata ATCC 2001 were the most sensitive strains, as the extract inhibited their virulence factors. In silico analysis indicated that vismione D presented the best antifungal activity, since it was the most effective in inhibiting CaCYP51, and may act as anti-inflammatory and antioxidant agent, according to the online PASS prediction. Overall, the data demonstrate that EHVG has an anti-Candida effect by inhibiting virulence factors of the fungi. This activity may be related to its vismione D content, indicating this compound may represent a new perspective for treating diseases caused by Candida sp.

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Isoliensinine: A Natural Compound with “Drug-Like” Potential

Cited by 20 publications

References 73 publications

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

Isoliensinine Suppresses Osteoclast Formation Through NF-κB Signaling Pathways and Relieves Ovariectomy-Induced Bone Loss

The Anti-Virulence Effect of Vismia guianensis against Candida albicans and Candida glabrata

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