Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents
Ginger (<i>Zingiber officinale</i>) is widely used as a spice and a traditional medicine. Many bioactivities have been reported for its extracts and the isolated compounds, including cardiovascular protective effects. Different pathways were suggested to contribute to these effects, like...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/12/3/744 |
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| author | Sara H. H. Ahmed Tímea Gonda Orinamhe G. Agbadua Gábor Girst Róbert Berkecz Norbert Kúsz Meng-Chun Tsai Chin-Chung Wu György T. Balogh Attila Hunyadi |
| author_facet | Sara H. H. Ahmed Tímea Gonda Orinamhe G. Agbadua Gábor Girst Róbert Berkecz Norbert Kúsz Meng-Chun Tsai Chin-Chung Wu György T. Balogh Attila Hunyadi |
| author_sort | Sara H. H. Ahmed |
| collection | DOAJ |
| description | Ginger (<i>Zingiber officinale</i>) is widely used as a spice and a traditional medicine. Many bioactivities have been reported for its extracts and the isolated compounds, including cardiovascular protective effects. Different pathways were suggested to contribute to these effects, like the inhibition of platelet aggregation. In this study, we synthesised fourteen 6-gingerol derivatives, including eight new compounds, and studied their antiplatelet, COX-1 inhibitor, and antioxidant activities. In silico docking of selected compounds to <i>h</i>-COX-1 enzyme revealed favourable interactions. The investigated 6-gingerol derivatives were also characterised by in silico and experimental physicochemical and blood–brain barrier-related parameters for lead and preclinical candidate selection. 6-Shogaol (<b>2</b>) was identified as the best overall antiplatelet lead, along with compounds <b>3</b> and <b>11</b> and the new compound <b>17</b>, which require formulation to optimize their water solubility. Compound <b>5</b> was identified as the most potent antioxidant that is also promising for use in the central nervous system (CNS). |
| first_indexed | 2024-03-11T07:00:10Z |
| format | Article |
| id | doaj.art-1094c03688cd4d36853bffeafc84a2e3 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-11T07:00:10Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-1094c03688cd4d36853bffeafc84a2e32023-11-17T09:19:10ZengMDPI AGAntioxidants2076-39212023-03-0112374410.3390/antiox12030744Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet AgentsSara H. H. Ahmed0Tímea Gonda1Orinamhe G. Agbadua2Gábor Girst3Róbert Berkecz4Norbert Kúsz5Meng-Chun Tsai6Chin-Chung Wu7György T. Balogh8Attila Hunyadi9Institute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmaceutical Analysis, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, TaiwanGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, TaiwanInstitute of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, HungaryInstitute of Pharmacognosy, University of Szeged, H-6720 Szeged, HungaryGinger (<i>Zingiber officinale</i>) is widely used as a spice and a traditional medicine. Many bioactivities have been reported for its extracts and the isolated compounds, including cardiovascular protective effects. Different pathways were suggested to contribute to these effects, like the inhibition of platelet aggregation. In this study, we synthesised fourteen 6-gingerol derivatives, including eight new compounds, and studied their antiplatelet, COX-1 inhibitor, and antioxidant activities. In silico docking of selected compounds to <i>h</i>-COX-1 enzyme revealed favourable interactions. The investigated 6-gingerol derivatives were also characterised by in silico and experimental physicochemical and blood–brain barrier-related parameters for lead and preclinical candidate selection. 6-Shogaol (<b>2</b>) was identified as the best overall antiplatelet lead, along with compounds <b>3</b> and <b>11</b> and the new compound <b>17</b>, which require formulation to optimize their water solubility. Compound <b>5</b> was identified as the most potent antioxidant that is also promising for use in the central nervous system (CNS).https://www.mdpi.com/2076-3921/12/3/744ginger6-gingerolcardiovascular diseaseantiplateletcyclooxygenase-1antioxidant |
| spellingShingle | Sara H. H. Ahmed Tímea Gonda Orinamhe G. Agbadua Gábor Girst Róbert Berkecz Norbert Kúsz Meng-Chun Tsai Chin-Chung Wu György T. Balogh Attila Hunyadi Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents Antioxidants ginger 6-gingerol cardiovascular disease antiplatelet cyclooxygenase-1 antioxidant |
| title | Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents |
| title_full | Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents |
| title_fullStr | Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents |
| title_full_unstemmed | Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents |
| title_short | Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents |
| title_sort | preparation and evaluation of 6 gingerol derivatives as novel antioxidants and antiplatelet agents |
| topic | ginger 6-gingerol cardiovascular disease antiplatelet cyclooxygenase-1 antioxidant |
| url | https://www.mdpi.com/2076-3921/12/3/744 |
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