Journal of Biomolecular Structure and Dynamics, 2022
The flavonoid based 7-hydroxy flavone (PubChem CID: 5281894; molecular formula: C15H10O3) molecul... more The flavonoid based 7-hydroxy flavone (PubChem CID: 5281894; molecular formula: C15H10O3) molecule has been isolated for the first time from the methanolic extract from the leaves of Avicennia officinalis L. in the tropical mangrove ecosystem of Andaman and Nicobar Islands (ANI), India. The molecular structure of bioactive compound was characterized by spectroscopic analysis, including FT-IR, 1H, 13C NMR spectroscopy and ESI-HRMS and elucidated as 7-hydroxy flavone. An anticancer activity of isolated 7-hydroxy flavone was evaluated by in vitro study against two different human cancer cell lines namely, HeLa (cervical cells) and MDA-MB231 (breast cells) and they exhibited promising anticancer activity with IC50 values are 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL, respectively. The antioxidant property of 7-hydroxy flavone at a standard concentration of 50 µg, was found to be (IC50) 5.5486 ± 0.81 µg/mL. In summary, this investigation provides evidence that 7-hydroxy flavone exhibits both anticancer and antioxidant properties. Meanwhile, the antimicrobial activity ability of 7-hydroxy flavone were also evaluated using three Gram positive and two Gram negative strain exhibited no antimicrobial activities. Density-functional theory (DFT) studies confirm the structure is global minima in the PES, from the optimized geometry FMO and MESP map analyzed. Further, the molecular docking and molecular dynamics simulation studies result shows that 7-hydroxy flavone has the better binding ability with anti-apoptotic Bcl-2 protein with the estimated free energy of binding of -6.3 kcal/mol. This bioactive compound may be act as drug candidate for treating various kinds of cancers. HighlightsA 7-hydroxy flavone molecule has been isolated from Avicennia officinalis.The isolated pure compound was subjected to spectral analysis such as FT-IR, 1H NMR, 13C NMR spectral data and HRMS analysis for skeleton of the molecule.The anticancer activity of 7-hydroxy flavone studied against Cervical (HeLa) cancer cell lines and breast (MDA-MB231) cancer cell lines with the IC50 values of 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL), respectively.The antioxidant properties of 7-hydroxy flavone were found to be (IC50) 5.5486 ± 0.81 µg/mL at a standard concentration of 50 µg.DFT, molecular docking and MD simulation results explained that 7-hydroxy flavone could be the most promising candidate to inhibit the function of anti-apoptotic Bcl-2 protein in cancerous cell.Communicated by Ramaswamy H. Sarma.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
In this present study, the sugar based bioactive molecule, 2-methoxy mucic acid ( 4) was isolated... more In this present study, the sugar based bioactive molecule, 2-methoxy mucic acid ( 4) was isolated for the first time from the methanolic extract from the leaves of Rhizophora apiculata . The structure of compound was well characterized by different spectroscopic analysis, including FT-IR, 1 H, 13 C NMR spectroscopy and HRMS. Anticancer activity of 2-methoxy mucic acid ( 4 ) was evaluated against HeLa and MDA-MB231 cancer cell lines and they displayed promising activity with the IC 50 values of 22.88283±0.72 µg/ml in HeLa and 2.91925±0.52 µg/ml in case of MDA-MB231, respectively. The antioxidant property of 2-methoxy mucic acid ( 4 ) was found to be (IC 50 ) 21.361±0.41 µg/ml. Apart from in vitro studies, we also performed extensive in silico studies (molecular docking and molecular dynamics simulation) on four key anti-apoptotic Bcl-2 family members (Bcl-2, Bcl-w, Bcl-xL and Bcl-B) towards 2-methoxy mucic acid ( 4) and the results revealed that this molecule showed higher binding af...
Journal of Biomolecular Structure and Dynamics, 2020
Abstract Gallic acid (PubChem CID: 370) and quercetin (PubChem CID: 5280343) are major phenolic c... more Abstract Gallic acid (PubChem CID: 370) and quercetin (PubChem CID: 5280343) are major phenolic compounds in many mangrove plants that have been related to health cure. In the present study, the active fractions namely gallic acid (1) and quercetin (2) were isolated from the methanolic extract of leaves of Ceriops tagal in a Tropical mangrove ecosystem of Andaman and Nicobar Island (ANI), India. The chemical structures were determined by spectroscopic analysis: Fourier-Transform Infrared spectroscopy (FT-IR), 1H, 13C Nuclear Magnetic Resonance (NMR) spectroscopy, and High-resolution mass spectrometry (HRMS). The anticancer activity of isolated compounds (1) and (2) were evaluated by in vitro assays against two human cancer cell lines namely, HeLa (Cervical) and MDA-MB231 (Breast) cancer cells revealed that IC50 values of gallic acid (HeLa: 4.179197 ± 0.45 µg/ml; MDA-MB231: 80.0427 ± 0.19 µg/ml at 24 h) and quercetin (HeLa: 99.914 ± 0.18 µg/ml; MDA-MB231: 18.288382 ± 0.12 µg/ml at 24 h), respectively. Antioxidant properties of gallic acid (1) and quercetin (2) are found to be IC50 value of 0.77 ± 0.41 µg/ml and 1.897 ± 0.81 µg/ml, respectively. Molecular docking results explained that gallic acid (1) and quercetin (2) showed estimated binding free energy (ΔG) of −5.4 and −6.9 kcal/mol towards drug target Bcl-B protein, respectively. The estimated inhibition constant (Ki) for these two molecules are 110 and 8.75 μM, respectively. The MD simulation additionally supported that quercetin molecule is significantly improved the structural stability of Bcl-B protein. The present study provides key insights about the importance of polyphenols, and thus leads to open the therapeutic route for anti-cancer drug discovery process. Communicated by Ramaswamy H. Sarma
We have described the simple, convenient and high yielding one-pot synthesis of a library of high... more We have described the simple, convenient and high yielding one-pot synthesis of a library of highly functionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by creation of two C-C bonds and one C-N bond, all of them taking place in a single synthetic operation. As the products precipitate out of the reaction simple filtration is enough to gather the products and thus, there is no need for work-up or column-chromatography. The C6-methylsulfanyl group in the product 1,4-DHPs was substituted with primary and secondary amines to provide 1,4-DHPs with further possibilities in structural diversity. As a demonstration of application of the method we have synthesised an analogue of nitenpyram, a neonicotinoid insecticide.
We have described the simple, convenient and high yielding one-pot synthesis of a library of high... more We have described the simple, convenient and high yielding one-pot synthesis of a library of highly func-tionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by creation of two C–C bonds and one C–N bond, all of them taking place in a single synthetic operation. As the products precipitate out of the reaction simple filtration is enough to gather the products and thus, there is no need for work-up or column-chromatography. The C6-methylsulfanyl group in the product 1,4-DHPs was substituted with primary and secondary amines to provide 1,4-DHPs with further possibilities in structural diversity. As a demonstration of application of the method we have synthesised an analogue of nitenpyram, a neonicotinoid insecticide.
A series of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives 8 were synthesized fr... more A series of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives 8 were synthesized from 2-((E)-2-nitrovinyl)phenol 7 and ((E)-N-methyl)-1-(methylthio)-2-nitroethenamine 5. The cytotoxic activity of these molecules was tested against two cancer cell lines namely HeLa (cervical cancer) and HEp-2 (epidermoid laryngeal carcinoma). Among them, two molecules (4H-chromenes 8h and 8i) displayed potent anti-proliferative activity with IC50 values of 115.04 and 18.96 μM for HeLa and 86.94 and 25.08 μM for Hep-2 cell lines, respectively. Morphological evaluation of the cell lines revealed that both 8h and 8i induce the apoptotic process. Molecular docking studies of all the 4H-chromenes 8 with anti-apoptotic Bcl-2, Bcl-w, and Bcl-xL proteins revealed that the 4H-chromenes 8h and 8i have good docking score and thus corroborated in vitro studies. Furthermore, evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles. Thus, 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development.
Journal of Biomolecular Structure and Dynamics, 2022
The flavonoid based 7-hydroxy flavone (PubChem CID: 5281894; molecular formula: C15H10O3) molecul... more The flavonoid based 7-hydroxy flavone (PubChem CID: 5281894; molecular formula: C15H10O3) molecule has been isolated for the first time from the methanolic extract from the leaves of Avicennia officinalis L. in the tropical mangrove ecosystem of Andaman and Nicobar Islands (ANI), India. The molecular structure of bioactive compound was characterized by spectroscopic analysis, including FT-IR, 1H, 13C NMR spectroscopy and ESI-HRMS and elucidated as 7-hydroxy flavone. An anticancer activity of isolated 7-hydroxy flavone was evaluated by in vitro study against two different human cancer cell lines namely, HeLa (cervical cells) and MDA-MB231 (breast cells) and they exhibited promising anticancer activity with IC50 values are 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL, respectively. The antioxidant property of 7-hydroxy flavone at a standard concentration of 50 µg, was found to be (IC50) 5.5486 ± 0.81 µg/mL. In summary, this investigation provides evidence that 7-hydroxy flavone exhibits both anticancer and antioxidant properties. Meanwhile, the antimicrobial activity ability of 7-hydroxy flavone were also evaluated using three Gram positive and two Gram negative strain exhibited no antimicrobial activities. Density-functional theory (DFT) studies confirm the structure is global minima in the PES, from the optimized geometry FMO and MESP map analyzed. Further, the molecular docking and molecular dynamics simulation studies result shows that 7-hydroxy flavone has the better binding ability with anti-apoptotic Bcl-2 protein with the estimated free energy of binding of -6.3 kcal/mol. This bioactive compound may be act as drug candidate for treating various kinds of cancers. HighlightsA 7-hydroxy flavone molecule has been isolated from Avicennia officinalis.The isolated pure compound was subjected to spectral analysis such as FT-IR, 1H NMR, 13C NMR spectral data and HRMS analysis for skeleton of the molecule.The anticancer activity of 7-hydroxy flavone studied against Cervical (HeLa) cancer cell lines and breast (MDA-MB231) cancer cell lines with the IC50 values of 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL), respectively.The antioxidant properties of 7-hydroxy flavone were found to be (IC50) 5.5486 ± 0.81 µg/mL at a standard concentration of 50 µg.DFT, molecular docking and MD simulation results explained that 7-hydroxy flavone could be the most promising candidate to inhibit the function of anti-apoptotic Bcl-2 protein in cancerous cell.Communicated by Ramaswamy H. Sarma.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
In this present study, the sugar based bioactive molecule, 2-methoxy mucic acid ( 4) was isolated... more In this present study, the sugar based bioactive molecule, 2-methoxy mucic acid ( 4) was isolated for the first time from the methanolic extract from the leaves of Rhizophora apiculata . The structure of compound was well characterized by different spectroscopic analysis, including FT-IR, 1 H, 13 C NMR spectroscopy and HRMS. Anticancer activity of 2-methoxy mucic acid ( 4 ) was evaluated against HeLa and MDA-MB231 cancer cell lines and they displayed promising activity with the IC 50 values of 22.88283±0.72 µg/ml in HeLa and 2.91925±0.52 µg/ml in case of MDA-MB231, respectively. The antioxidant property of 2-methoxy mucic acid ( 4 ) was found to be (IC 50 ) 21.361±0.41 µg/ml. Apart from in vitro studies, we also performed extensive in silico studies (molecular docking and molecular dynamics simulation) on four key anti-apoptotic Bcl-2 family members (Bcl-2, Bcl-w, Bcl-xL and Bcl-B) towards 2-methoxy mucic acid ( 4) and the results revealed that this molecule showed higher binding af...
Journal of Biomolecular Structure and Dynamics, 2020
Abstract Gallic acid (PubChem CID: 370) and quercetin (PubChem CID: 5280343) are major phenolic c... more Abstract Gallic acid (PubChem CID: 370) and quercetin (PubChem CID: 5280343) are major phenolic compounds in many mangrove plants that have been related to health cure. In the present study, the active fractions namely gallic acid (1) and quercetin (2) were isolated from the methanolic extract of leaves of Ceriops tagal in a Tropical mangrove ecosystem of Andaman and Nicobar Island (ANI), India. The chemical structures were determined by spectroscopic analysis: Fourier-Transform Infrared spectroscopy (FT-IR), 1H, 13C Nuclear Magnetic Resonance (NMR) spectroscopy, and High-resolution mass spectrometry (HRMS). The anticancer activity of isolated compounds (1) and (2) were evaluated by in vitro assays against two human cancer cell lines namely, HeLa (Cervical) and MDA-MB231 (Breast) cancer cells revealed that IC50 values of gallic acid (HeLa: 4.179197 ± 0.45 µg/ml; MDA-MB231: 80.0427 ± 0.19 µg/ml at 24 h) and quercetin (HeLa: 99.914 ± 0.18 µg/ml; MDA-MB231: 18.288382 ± 0.12 µg/ml at 24 h), respectively. Antioxidant properties of gallic acid (1) and quercetin (2) are found to be IC50 value of 0.77 ± 0.41 µg/ml and 1.897 ± 0.81 µg/ml, respectively. Molecular docking results explained that gallic acid (1) and quercetin (2) showed estimated binding free energy (ΔG) of −5.4 and −6.9 kcal/mol towards drug target Bcl-B protein, respectively. The estimated inhibition constant (Ki) for these two molecules are 110 and 8.75 μM, respectively. The MD simulation additionally supported that quercetin molecule is significantly improved the structural stability of Bcl-B protein. The present study provides key insights about the importance of polyphenols, and thus leads to open the therapeutic route for anti-cancer drug discovery process. Communicated by Ramaswamy H. Sarma
We have described the simple, convenient and high yielding one-pot synthesis of a library of high... more We have described the simple, convenient and high yielding one-pot synthesis of a library of highly functionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by creation of two C-C bonds and one C-N bond, all of them taking place in a single synthetic operation. As the products precipitate out of the reaction simple filtration is enough to gather the products and thus, there is no need for work-up or column-chromatography. The C6-methylsulfanyl group in the product 1,4-DHPs was substituted with primary and secondary amines to provide 1,4-DHPs with further possibilities in structural diversity. As a demonstration of application of the method we have synthesised an analogue of nitenpyram, a neonicotinoid insecticide.
We have described the simple, convenient and high yielding one-pot synthesis of a library of high... more We have described the simple, convenient and high yielding one-pot synthesis of a library of highly func-tionalized hexa-substituted 1,4-dihydropyridines (1,4-DHPs) by 2-aminopyridine catalysed pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes. This domino transformation involves formation of dihydropyridine ring by creation of two C–C bonds and one C–N bond, all of them taking place in a single synthetic operation. As the products precipitate out of the reaction simple filtration is enough to gather the products and thus, there is no need for work-up or column-chromatography. The C6-methylsulfanyl group in the product 1,4-DHPs was substituted with primary and secondary amines to provide 1,4-DHPs with further possibilities in structural diversity. As a demonstration of application of the method we have synthesised an analogue of nitenpyram, a neonicotinoid insecticide.
A series of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives 8 were synthesized fr... more A series of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives 8 were synthesized from 2-((E)-2-nitrovinyl)phenol 7 and ((E)-N-methyl)-1-(methylthio)-2-nitroethenamine 5. The cytotoxic activity of these molecules was tested against two cancer cell lines namely HeLa (cervical cancer) and HEp-2 (epidermoid laryngeal carcinoma). Among them, two molecules (4H-chromenes 8h and 8i) displayed potent anti-proliferative activity with IC50 values of 115.04 and 18.96 μM for HeLa and 86.94 and 25.08 μM for Hep-2 cell lines, respectively. Morphological evaluation of the cell lines revealed that both 8h and 8i induce the apoptotic process. Molecular docking studies of all the 4H-chromenes 8 with anti-apoptotic Bcl-2, Bcl-w, and Bcl-xL proteins revealed that the 4H-chromenes 8h and 8i have good docking score and thus corroborated in vitro studies. Furthermore, evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles. Thus, 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development.
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