Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies
Anthraquinones and coumarins have excellent pharmacological activities and are an important class of natural plant metabolites with various biological activities. In this study, anthraquinone-9,10-dione and coumarin derivatives were combined to develop a novel anthraquinone-connected coumarin-deriva...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-02-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402401199X |
| _version_ | 1797304511208882176 |
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| author | Velmurugan Loganathan Anis Ahamed Surendrakumar Radhakrishnan Abdel-Rhman Z. Gaafar Raman Gurusamy Idhayadhulla Akbar |
| author_facet | Velmurugan Loganathan Anis Ahamed Surendrakumar Radhakrishnan Abdel-Rhman Z. Gaafar Raman Gurusamy Idhayadhulla Akbar |
| author_sort | Velmurugan Loganathan |
| collection | DOAJ |
| description | Anthraquinones and coumarins have excellent pharmacological activities and are an important class of natural plant metabolites with various biological activities. In this study, anthraquinone-9,10-dione and coumarin derivatives were combined to develop a novel anthraquinone-connected coumarin-derivative sequence. The synthesised novel anthraquinone-connected coumarin derivatives (1a-t) were screened for in vitro antibacterial, antioxidant, and tyrosinase inhibitory activities. The antibacterial activities of the synthesised compounds (1a–t) were tested against both gram-positive and gram-negative bacteria. Specifically, compound 1t was more active against E. aerogenes than ciprofloxacin. With regard to antioxidant activity, compound 1o (50.68 % at 100 μg/mL) was highly active compared to the other compounds, whereas it was less active than the standard BHT (76.74 % at 100 μg/mL). In terms of compound 1r (9.31 ± 0.45 μg/mL) was highly active against tyrosinase inhibitory activity compared with kojic acid (10.42 ± 0.98 μg/mL). In the molecular docking study, compound 1r had a higher docking score (−8.8 kcal mol−1) than kojic acid (−1.7 kcal mol−1). DFT calculations were performed to determine the energy gap of highly active compound 1r (ΔE = 0.11) and weakly active compound 1a (ΔE = 0.12). In this study, we found that every molecule displayed significant antibacterial, antioxidant, and tyrosinase inhibitory properties. Based on these reports, compounds 1r and 1t may act as multi-target agents. |
| first_indexed | 2024-03-08T00:11:34Z |
| format | Article |
| id | doaj.art-db42815051764c43b5e1e050739b9018 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-08T00:11:34Z |
| publishDate | 2024-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-db42815051764c43b5e1e050739b90182024-02-17T06:39:53ZengElsevierHeliyon2405-84402024-02-01103e25168Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studiesVelmurugan Loganathan0Anis Ahamed1Surendrakumar Radhakrishnan2Abdel-Rhman Z. Gaafar3Raman Gurusamy4Idhayadhulla Akbar5Research Department of Chemistry, Nehru Memorial College (Affiliated Bharathidasan University), Puthanampatti, Tamil Nadu, 621007, IndiaDepartment of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi ArabiaResearch Department of Chemistry, Nehru Memorial College (Affiliated Bharathidasan University), Puthanampatti, Tamil Nadu, 621007, IndiaDepartment of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi ArabiaDepartment of Life Sciences, Yeungnam University, Gyeongsan, 38541, Gyeongsan-buk, South KoreaResearch Department of Chemistry, Nehru Memorial College (Affiliated Bharathidasan University), Puthanampatti, Tamil Nadu, 621007, India; Corresponding author.Anthraquinones and coumarins have excellent pharmacological activities and are an important class of natural plant metabolites with various biological activities. In this study, anthraquinone-9,10-dione and coumarin derivatives were combined to develop a novel anthraquinone-connected coumarin-derivative sequence. The synthesised novel anthraquinone-connected coumarin derivatives (1a-t) were screened for in vitro antibacterial, antioxidant, and tyrosinase inhibitory activities. The antibacterial activities of the synthesised compounds (1a–t) were tested against both gram-positive and gram-negative bacteria. Specifically, compound 1t was more active against E. aerogenes than ciprofloxacin. With regard to antioxidant activity, compound 1o (50.68 % at 100 μg/mL) was highly active compared to the other compounds, whereas it was less active than the standard BHT (76.74 % at 100 μg/mL). In terms of compound 1r (9.31 ± 0.45 μg/mL) was highly active against tyrosinase inhibitory activity compared with kojic acid (10.42 ± 0.98 μg/mL). In the molecular docking study, compound 1r had a higher docking score (−8.8 kcal mol−1) than kojic acid (−1.7 kcal mol−1). DFT calculations were performed to determine the energy gap of highly active compound 1r (ΔE = 0.11) and weakly active compound 1a (ΔE = 0.12). In this study, we found that every molecule displayed significant antibacterial, antioxidant, and tyrosinase inhibitory properties. Based on these reports, compounds 1r and 1t may act as multi-target agents.http://www.sciencedirect.com/science/article/pii/S240584402401199XAnthraquinoneAntibacterial activityAntioxidant activityCoumarinDFT calculationMolecular docking |
| spellingShingle | Velmurugan Loganathan Anis Ahamed Surendrakumar Radhakrishnan Abdel-Rhman Z. Gaafar Raman Gurusamy Idhayadhulla Akbar Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies Heliyon Anthraquinone Antibacterial activity Antioxidant activity Coumarin DFT calculation Molecular docking |
| title | Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies |
| title_full | Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies |
| title_fullStr | Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies |
| title_full_unstemmed | Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies |
| title_short | Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies |
| title_sort | synthesis of anthraquinone connected coumarin derivatives via grindstone method and their evaluation of antibacterial antioxidant tyrosinase inhibitory activities with molecular docking and dft calculation studies |
| topic | Anthraquinone Antibacterial activity Antioxidant activity Coumarin DFT calculation Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S240584402401199X |
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