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.
Preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone
-
Paragraph 0029; 0038; 0040, (2018/07/15)
The invention discloses a preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone and relates to the field of medicinal chemistry. The method comprises the steps as follows: 1) 4-(4-hydroxy-3-methoxyphenyl)-2-butanone is dissolved in a halogenated hydrocarbon solvent, pyrrolidine or piperidine is added at the room temperature, and the mixture reacts for 15-120 min; 2) a halogenated hydrocarbon solution of n-hexaldehyde is added, and the mixture reacts for 2-24 h; 3) an inorganic base solution is added, the mixture reacts for 1-24 h, aftertreatment is performed, and a compoundshown in formula (1) is prepared. Reactions at the room temperature are conducted with inorganic base and other weak bases, and the total yield is 78% or above. The method has mild reaction conditionsand is convenient to operate and suitable for industrial production.
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