Gramine (GRM), which occurs in Gramineae plants, has been developed to be a biological insecticide. Exposure to GRM was reported to induce elevations of serum ALT and AST in rats, but the mechanisms of the observed hepatotoxicity have not been elucidated. The present study aimed to identify reactive metabolites that potentially participate in the toxicity. In rat liver microsomal incubations fortified with glutathione or N-acetylcysteine, one oxidative metabolite (M1), one glutathione conjugate (M2), and one N-acetylcysteine conjugate (M3) were detected after exposure to GRM. The corresponding conjugates were detected in the bile and urine of rats after GRM administration. CYP3A was the main enzyme mediating the metabolic activation of GRM. The detected GSH and NAC conjugates suggest that GRM was metabolized to a quinone imine intermediate. Both GRM and M1 showed significant toxicity to rat primary hepatocytes.
In this work, a series of hydrophobic ionic liquids (ILs) with ClO 4 − , BF 4 − , PF 6 − , CF 3 SO 3 − and bis(trifluoromethanesulphonyl)imide (NTf 2 − ) as anions were synthesized. Their extraction ability for the two alkaloids, quinine and gramine was studied. The experimental results suggested that the extraction ability of ILs had no clear relationship with the alkyl chain length on the IL cation but depended on the hydrophobicity and hydrogen-bonding strength of the IL anion. The CF 3 SO 3 − -based ILs were stable against hydrolysis and exhibited better extraction ability for the two alkaloids. Thermodynamic analysis suggested that the extraction of the two alkaloids was an entropy-driven process. These results indicate that CF 3 SO 3 − -based ILs are ideal solvents for recovering alkaloids from the water phase.
Basing on the previous syntheses of ester compounds containing gramine functional groups, the researchers synthesized two novel acylamino compounds containing gramine groups and the structures of target compound were established using 1 HNMR, 13 CNMR, IR spectra, and elemental analysis. The antibacterial activity of the synthesized compounds against Escherichia coli and Staphylococcus aureus , as well as their antifouling activity were studied. The results showed that these compounds possessed high antibacterial activity and a minimal inhibitory concentration value of 0.03 mg/mL against bacteria. Moreover, their antifouling properties are superior to cuprous oxide and chlorothalonil, which are widely used as antifoulants. Furthermore, quantitative structure activity relationship studies with antibacterial activity of the nine gramine compounds were established. These provide theoretical and technical bases for preparing environment-friendly antifouling coatings with the compounds as antifouling agents.
危险品化学品经营许可证（带存储）