6‐Gingerol and Semisynthetic 6‐Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish
| Autor: | Tamilvelan Manjunathan, Pushparathinam Gopinath, Jesu Arokiaraj, Ajay Guru |
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| Rok vydání: | 2021 |
| Předmět: |
Antioxidant
DPPH medicine.medical_treatment Catechols Bioengineering Ginger medicine.disease_cause Biochemistry Antioxidants Lipid peroxidation chemistry.chemical_compound Picrates In vivo medicine Animals Humans Benzothiazoles Molecular Biology Zebrafish chemistry.chemical_classification Reactive oxygen species ABTS Cell Death Biphenyl Compounds Guaiacol Acridine orange Hydrogen Peroxide General Chemistry General Medicine Oxidative Stress chemistry Molecular Medicine Fatty Alcohols Sulfonic Acids Reactive Oxygen Species Oxidative stress |
| Zdroj: | Chemistry & Biodiversity. 18 |
| ISSN: | 1612-1880 1612-1872 |
| Popis: | 6-gingerol ( 1 ) is one of the major components in ginger and developing new synthetic methodologies could bring semisynthetic analogs with improved therapeutic properties. Towards this, multigram scale isolation of 6-gingerol with excellent purity was optimized using a simple and robust extraction, followed by column purification. Synthesis of 6-gingerdione, 7 from 6-gingerol was then achieved through selective -OTBDMS protection, DMP oxidation and deprotection reaction sequence for the first time. Compounds 1 , 7 and 8 (dehydrozingerone) exhibited excellent cell-free antioxidant properties in DPPH, ABTS, superoxide radical scavenging assay and H2O2 assay at 10-50 microM concentrations. The hemolytic study suggests that up to 50 microM, all three compounds didn't exhibit toxicity to human erythrocytes. When H2O2 treated zebrafish larvae groups (96hpf) were exposed to compounds 1 , 7 and 8 , it increases the SOD (19, 19.1 and 18.7 U/mg protein), CAT (18.1, 16.5, and 15.8 micromol/mg levels and decreases the lipid peroxidation level (13, 15 and 18 nmol/mg protein) respectively. In vivo ROS levels and degree of cell death were studied using DCFDA and Acridine orange assays. Compounds 1 , 7 and 8 decreases the ROS and cell death level significantly. Taken together, compounds 1 , 7 and 8 exhibit excellent antioxidant properties, counteract H2O2 induced oxidative stress, reduces cell death in zebrafish larvae. |
| Databáze: | OpenAIRE |
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