Potential Anti-Cancer Flavonoids Isolated From <i>Caesalpinia bonduc</i> Young Twigs and Leaves: Molecular Docking and In Silico Studies

Iheagwam, Franklyn Nonso; Ogunlana, Olubanke Olujoke; Ogunlana, Oluseyi Ebenezer; Isewon, Itunuoluwa; Oyelade, Jelili

doi:10.1177/1177932218821371

Cited by 57 publications

(35 citation statements)

References 43 publications

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“…The best binding conformation of phytocompounds against target proteins were determined based on the lowest total binding energy among the different conformations generated. The identified phytocompounds were imported into the iGEMDOCK graphical user interface and were sorted by the post-docking analysis based on their binding energies and compound fitness score measured by the iGEMDOCK docking algorithm 64 . To determine the relative strengths of the binding interactions of the best identified phytocompound, screening for its best binding pose and the series of energy values, such as binding energy, ligand efficiency, inhibition constant and Van der Waals (VDW) + hydrogen bonding (Hbond) + desolvation energy of each target protein, were analyzed using the AutoDOCK program.…”

Section: Discussionmentioning

confidence: 99%

GC–MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins

Konappa

Udayashankar

Krishnamurthy

et al. 2020

Sci Rep

148

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Amomum nilgiricum is one of the plant species reported from Western Ghats of India, belonging to the family Zingiberaceae, with ethno-botanical values, and is well-known for their ethno medicinal applications. In the present investigation, ethyl acetate and methanol extracts of A. nilgiricum were analyzed by Fourier transform infrared spectrometer (FTIR) and gas chromatography-mass spectrometry (GC–MS) to identify the important functional groups and phytochemical constituents. The FTIR spectra revealed the occurrence of functional characteristic peaks of aromatic amines, carboxylic acids, ketones, phenols and alkyl halides group from leaf and rhizome extracts. The GC–MS analysis of ethyl acetate and methanol extracts from leaves, and methanol extract from rhizomes of A. nilgiricum detected the presence of 25 phytochemical compounds. Further, the leaf and rhizome extracts of A. nilgiricum showed remarkable antibacterial and antifungal activities at 100 mg/mL. The results of DPPH and ferric reducing antioxidant power assay recorded maximum antioxidant activity in A. nilgiricum methanolic leaf extract. While, ethyl acetate leaf extract exhibited maximum α-amylase inhibition activity, followed by methanolic leaf extract exhibiting aldose reductase inhibition. Subsequently, these 25 identified compounds were analyzed for their bioactivity through in silico molecular docking studies. Results revealed that among the phytochemical compounds identified, serverogenin acetate might have maximum antibacterial, antifungal, antiviral, antioxidant and antidiabetic properties followed by 2,4-dimethyl-1,3-dioxane and (1,3-13C2)propanedioic acid. To our best knowledge, this is the first description on the phytochemical constituents of the leaves and rhizomes of A. nilgiricum, which show pharmacological significance, as there has been no literature available yet on GC–MS and phytochemical studies of this plant species. The in silico molecular docking of serverogenin acetate was also performed to confirm its broad spectrum activities based on the binding interactions with the antibacterial, antifungal, antiviral, antioxidant and antidiabetic target proteins. The results of the present study will create a way for the invention of herbal medicines for several ailments by using A. nilgiricum plants, which may lead to the development of novel drugs.

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Section: Discussionmentioning

confidence: 99%

GC–MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins

Konappa

Udayashankar

Krishnamurthy

et al. 2020

Sci Rep

148

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“…In lead compound development, compliance of test compound physicochemical properties (molecular mass, number of hydrogen bond donors and acceptors and so on) to Lipinski rule of 5 (RO5) is imperative to avoid failure during clinical trials [35, 36]. Compounds that pass RO5 (usually with none or one default) are predicted to have optimal pharmacokinetic properties, consequently subjecting them further to molecular docking [13]. Since all compounds passed RO5, they may exhibit good pharmacokinetic properties.…”

Section: Discussionmentioning

confidence: 99%

“…The structures of the GC-MS identified compounds with ≥5% abundance were prepared as reported by Iheagwam et al [13]. The 3D structure of α -glucosidase and α -amylase was modelled using the crystal structures with PDB codes 5kzw and 1b2y, respectively, obtained from RCSB protein data bank as templates in SWISS-MODEL [14].…”

Section: Methodsmentioning

confidence: 99%

“…Virtual screening of selected identified ligands, analysis of drug-likeness using the rule of five (RO5), and molecular docking were carried out according to the methodology of Iheagwam et al [13]. However, grid dimensions of the binding pockets were 60 × 40 × 32 and 40 × 34 × 40 points separated by 1 Å for α -glucosidase and α -amylase, respectively.…”

Section: Methodsmentioning

confidence: 99%

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GC-MS Analysis and Inhibitory Evaluation of Terminalia catappa Leaf Extracts on Major Enzymes Linked to Diabetes

Iheagwam

Israel

Kayode

et al. 2019

Evidence-Based Complementary and Alternative Medicine

Self Cite

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Terminalia catappa leaves are used in managing both diabetes mellitus and its complications in Southwest Nigeria. However, its inhibitory activity on enzymes implicated in diabetes is not very clear. This study investigated the in vitro inhibitory properties and mode of inhibition of T. catappa leaf extracts on enzymes associated with diabetes. The study also identified some bioactive compounds as well as their molecular interaction in the binding pocket of these enzymes. Standard enzyme inhibition and kinetics assays were performed to determine the inhibitory effects of aqueous extract (TCA) and ethanol extract (TCE) of T. catappa leaves on α-glucosidase and α-amylase activities. The phytoconstituents of TCA and TCE were determined using GC-MS. Molecular docking of the phytocompounds was performed using Autodock Vina. TCA and TCE were the most potent inhibitors of α-glucosidase (IC50 = 3.28 ± 0.47 mg/mL) and α-amylase (IC50 = 0.24 ± 0.08 mg/mL), respectively. Both extracts displayed a mixed mode of inhibition on α-amylase activity, while mixed and noncompetitive modes of inhibition were demonstrated by TCA and TCE, respectively, on α-glucosidase activity. The GC-MS analytic chromatogram revealed the presence of 24 and 22 compounds in TCE and TCA, respectively, which were identified mainly as phenolic compounds, terpenes/terpenoids, fatty acids, and other phytochemicals. The selected compounds exhibited favourable interactions with the enzymes compared with acarbose. Overall, the inhibitory effect of T. catappa on α-amylase and α-glucosidase may be ascribed to the synergistic action of its rich phenolic and terpene composition giving credence to the hypoglycaemic nature of T. catappa leaves.

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“…Quercetin (Que), a flavonoid that is a permanent component in human diets as well as an agent in traditional Chinese medicine, has been widely used to treat cancer for a longtime. 10,11 However, the exact antitumor mechanism of Que is unclear. Several studies have showed that Que increased reactive oxygen species (ROS) production in hepatocellular cancer and prevented lipid oxidation in the cell membrane, whereas other studies have indicated that Que could increase apoptotic rates in cancer cells.…”

Section: Introductionmentioning

confidence: 99%

<p>Quercetin Enhanced Paclitaxel Therapeutic Effects Towards PC-3 Prostate Cancer Through ER Stress Induction and ROS Production</p>

Zhang

Huang

et al. 2020

OTT

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Introduction: Prostate cancer is one of the most common cancers threatening public health worldwide. Although chemotherapy plays an important role in treating prostate cancer, it leads to many adverse effects and is prone to drug resistance. Quercetin, a natural product, is used in traditional Chinese medicine because of its strong antitumor activity and few side effects. Methods: In this study, we combined quercetin and paclitaxel to kill prostate cancer cells in vivo and in vitro, and we investigated the relevant mechanism of this combination treatment. After the cancer cells were treated with quercetin or/and paclitaxel, cell growth inhibition, apoptosis, the cell cycle, reactive oxygen species (ROS) generation, and several endoplasmic reticulum (ER) stress signaling pathway related gene expressions were evaluated. Results: The combined treatment with quercetin and paclitaxel significantly inhibited cell proliferation, increased apoptosis, arrested the cell cycle at the G2/M phase, inhibited cell migration, dramatically induced ER stress to occur, and increased ROS generation. In a PC-3 cancer-bearing murine model, this combination treatment exerted the most beneficial therapeutic effects, and quercetin increased the cancer cell-killing effects of paclitaxel, with nearly no side effects compared with the single paclitaxel treatment group. Conclusion: Combination treatment possessed enhanced anti-cancer effects, and these results will provide a basis for treating prostate cancer using a combination of quercetin and paclitaxel.

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Potential Anti-Cancer Flavonoids Isolated From Caesalpinia bonduc Young Twigs and Leaves: Molecular Docking and In Silico Studies

Cited by 57 publications

References 43 publications

GC–MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins

GC–MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins

GC-MS Analysis and Inhibitory Evaluation of Terminalia catappa Leaf Extracts on Major Enzymes Linked to Diabetes

<p>Quercetin Enhanced Paclitaxel Therapeutic Effects Towards PC-3 Prostate Cancer Through ER Stress Induction and ROS Production</p>

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