6‐Gingerol and Semisynthetic 6‐Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish. Issue 12 (27th October 2021)

• Record Type: Journal Article
• Authors: Manjunathan, Tamilvelan; Guru, Ajay; Arokiaraj, Jesu; Gopinath, Pushparathinam
• Is Part Of: Chemistry & biodiversity. Volume 18:Issue 12(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-10-27
• Subjects: antioxidant natural products -- developmental toxicity in zebrafish -- natural products from ginger -- semisynthetic modification isolation -- reactive oxygen species; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.202100650
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract: 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 H2 O2 assay at 10–50 μM concentrations. The hemolytic study suggests that up to 50 μM, all three compounds did not exhibit toxicity to human erythrocytes. When H2 O2 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 μmol/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 H2 O2 induced oxidative stress, reduces cell death in zebrafish larvae. Abstract :