6-Gingerol and Semisynthetic 6-Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish.
Chem Biodivers
; 18(12): e2100650, 2021 Dec.
Article
in En
| MEDLINE
| ID: mdl-34599795
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 10-50â
µM concentrations. The hemolytic study suggests that up to 50â
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 18.7â
U/mg protein), CAT (18.1, 16.5, and 15.8â
µmol/mg levels and decreases the lipid peroxidation level (13, 15 and 18â
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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Catechols
/
Reactive Oxygen Species
/
Fatty Alcohols
/
Guaiacol
/
Antioxidants
Limits:
Animals
/
Humans
Language:
En
Journal:
Chem Biodivers
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2021
Document type:
Article
Affiliation country:
India