Anti-inflammatory activity and cytotoxicity against ovarian cancer cell lines by amide alkaloids and piperic esters isolated from Piper longum fruits: In vitro assessments and molecular docking simulation

Phong, Nguyen Viet; Anh, Dinh Thi Nguyet; Chae, Ha Yeong; Yang, Seo Young; Kwon, Mi; Min, Byung Sun; Kim, Jeong Ah

doi:10.1016/j.bioorg.2022.106072

Cited by 14 publications

(10 citation statements)

References 73 publications

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“…Virtual screening based on molecular docking has been the most popular method for structure-based drug discovery since 1982 [ 28 ]. Researchers have characterized small-molecule activity at target protein-binding sites and disclosed basic biochemical processes using molecular docking models to depict the atomic-level interaction between a small molecule and a protein [ 29 ]. The two main processes in the docking procedure are predicting the ligand shape, location, and orientation at these sites and determining the binding energy [ 30 ].…”

Section: Discussionmentioning

confidence: 99%

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

et al. 2022

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Phloroglucinols—one of the major secondary metabolites in Dryopteris crassirhizoma—exhibit various pharmacological effects, such as antiviral, antioxidant, and antidiabetic activities. This study evaluated 30 phloroglucinols isolated from the rhizomes of D. crassirhizoma for their inhibitory activity on β-glucuronidase via in vitro assays. Among them, dimeric phloroglucinols 13–15 moderately inhibited β-glucuronidase, and trimeric phloroglucinols 26–28 showed strong inhibitory effects, with IC50 values ranging from 5.6 to 8.0 μM. Enzyme kinetic analysis confirmed all six active compounds to be in a competitive mode of inhibition. Molecular docking simulations revealed the key binding interactions with the active site of β-glucuronidase protein and the binding mechanisms of these active metabolites. Our results suggest that the rhizomes of D. crassirhizoma and trimeric compounds 26–28 may serve as potential candidates for discovering and developing new β-glucuronidase inhibitors.

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Section: Discussionmentioning

confidence: 99%

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

et al. 2022

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“…The grid box dimensions were set to x = 96, y = 96, z = 124; the grid position was set to x = 27.058, y = 28.677, z = 108.904; an exhaustiveness value of 100 was used, along with a number of binding modes of 1000, to comprehensively explore the protein-ligand interaction. The docking diagrams were examined and analysed using Discovery Studio Visualiser 21 22 .…”

Section: Methodsmentioning

confidence: 99%

Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg ( Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase using in vitro and in silico approaches

Oanh,

Phong,

Min

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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Two new neolignans, myrifralignans F–G ( 14 and 18 ), four new diarylnonanoid derivatives, myrifragranones A–D ( 21 – 24 ), and 18 known compounds were isolated and structurally elucidated from nutmeg ( Myristica fragrans Houtt.) seeds. The absolute configurations of these secondary metabolites were determined using the electronic circular dichroism technique. The inhibitory potential of these isolated compounds on soluble epoxide hydrolase (sEH) was investigated for the first time. Among them, malabaricones B and C ( 19 and 20 ) and four new compounds 21 – 24 displayed inhibitory activities against sEH, with IC 50 values ranging from 14.24 to 46.35 µM. Additionally, the binding mechanism, key binding interactions, stability, and dynamic behaviour of the active compounds with the sEH enzyme were analysed using in silico molecular docking and dynamics simulations. Our findings suggest that nutmeg could become a promising natural source for discovering and developing new sEH inhibitors.

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“…[1] Its fruit cluster, commonly known as long pepper, is widely applied as a spice and food ingredient. [2] In addition, the fruits of P. longum have a long history of wide clinical applications in traditional Chinese and Ayurveda medicines for treating diseases including diarrhea, vomiting, stomachache, toothache, and headache. Researches on P. longum revealed a variety of bioactivities such as anti-inflammatory, [3] immunomodulatory, [4] antitumor, [5] and neuroprotective effects.…”

Section: Introductionmentioning

confidence: 99%

“…Piper longum (Piperaceae) is a perennial herbaceous vine mainly distributed in South and Southeast Asian countries including India, Indonesia, Philippines, Vietnam and southern region of China [1] . Its fruit cluster, commonly known as long pepper, is widely applied as a spice and food ingredient [2] . In addition, the fruits of P. longum have a long history of wide clinical applications in traditional Chinese and Ayurveda medicines for treating diseases including diarrhea, vomiting, stomachache, toothache, and headache.…”

Section: Introductionmentioning

confidence: 99%

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Anti‐Diabetic Effects and Molecular Mechanisms of Amide Alkaloids fromPiper longumBased on Network Pharmacology Integrated with Cellular Assays

Gou

Liu

Abdubakiev

et al. 2022

Chemistry & Biodiversity

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Piper longum is a well‐known spice and traditional medicine. It was revealed to possess anti‐diabetic activity, but few information about its active component and underlying mechanism could be available. In this study, retrofractamides A (1) and C (2) isolated from P. longum showed potent inhibitory activity against PTP1B. Therefore, the potential mechanism was predicted by network pharmacology and molecular docking. PI3K/AKT was obtained as the most remarkable pathway against type 2 diabetes mellitus (T2DM), and AKT1 and GSK3β were yielded as the top two core targets of retrofractamides A (1) and C (2). Molecular docking of compounds with AKT1 and GSK3β showed strong binding affinity between them. Additionally, cellular experiments with a L6 cell model was conducted to further verify the above predictions. Results indicated that retrofractamides A (1) and C (2) exerted anti‐diabetic effect via activating PI3K/AKT pathway, and they promoted glucose consumption, glucose uptake, glycogen synthesis and glycolysis.

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Anti-inflammatory activity and cytotoxicity against ovarian cancer cell lines by amide alkaloids and piperic esters isolated from Piper longum fruits: In vitro assessments and molecular docking simulation

Cited by 14 publications

References 73 publications

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg ( Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase using in vitro and in silico approaches

Anti‐Diabetic Effects and Molecular Mechanisms of Amide Alkaloids fromPiper longumBased on Network Pharmacology Integrated with Cellular Assays

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