555-66-8Relevant articles and documents
6-Gingerol and Semisynthetic 6-Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish
Manjunathan, Tamilvelan,Guru, Ajay,Arokiaraj, Jesu,Gopinath, Pushparathinam
, (2021/11/03)
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 μM concentrations. The hemolytic study suggests that up to 50 μM, all three compounds did not 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 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 H2O2 induced oxidative stress, reduces cell death in zebrafish larvae.
Rapid synthesis method of shogaol compounds
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Paragraph 0031; 0032, (2018/03/26)
The invention relates to a rapid synthesis method of shogaol compounds. The specific reaction route is shown in the description. Compounds in formula (4) are obtained from dehydrozingerone and carbonic acid diester under the action of a base, dissolved in an organic solvent and subjected to hydrogenation reduction, key intermediate compounds shown in formula (5) are obtained and react with aliphatic aldehydes under the action of the base, and target compounds 6-shogaol in formula (1), 8-shogaol in formula (2) and 10-shogaol in formula (3) are obtained. The rapid synthesis method has the advantages that reaction yield is high, reaction conditions are mild, operation is simple and environment-friendliness is realized, and has good industrial application prospect.
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p