Scoparone is a major component of the shoot of Artemisia capillaris (Compositae), which has been used for the treatment of hepatitis and biliary tract infection in oriental countries. In the present study we observed that, scorparone exhibited no cytotoxic effect in unstimulated macrophages, but reduced the release of nitric oxide (NO) and prostaglandin E2 (PGE2) upon stimulation by IFN-gamma/LPS or LPS. The inhibitory effects were found to be in conjuction with the suppression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in IFN-gamma/LPS stimulated RAW 264.7 cells. Moreover, scoparone also attenuated the production of tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta and IL-6 in LPS-stimulated RAW264.7 cells. These results suggest that scoparone decreases the production of the inflammatory mediators such as NO and PGE2 in macrophages by inhibiting iNOS and COX-2 expression.

The hepatoprotective effects of chalcone derivatives were evaluated in D-galactosamine/lipopolysaccharide (D-GalN/LPS)-induced fulminant hepatic failure in mouse. Thirteen chalcone derivatives were synthesized for study and their hepatoprotective effects were evaluated by assessing aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels in serum. Chalcone preparations were injected into mice at 12 h and 1 h before intraperitoneal injection of D-GalN/LPS. After abdominal administration, changes in AST and ALT between the control and treated groups were observed. Ten of the synthesized chalcone derivatives exhibited inhibitory effects on D-GalN/LPS-induced levels of AST and ALT in mice. Compounds 2, 3, 8, 9, and 12 markedly reduced serum AST and ALT at 8 h, inhibited hepatocyte necrosis and showed significant hepatoprotective activities. The activity of compound 3 was compared with the bifendate (DDB) through oral administration. Compound 3 showed much higher inhibitory effects than bifendate for decreasing AST and ALT activity. The results indicate that compound 3 has strong hepatoprotective activity through suppression of tumor necrosis factor-alpha (TNF-alpha) preduction, reduction of the histological change in the liver, and attenuated of hepatocyte apoptosis confirmed by DNA fragmentation assay.

Addition reactions O 0060Addition of α,α-Difluoroiodomethyl Ketones to Alkenes with a Copper Catalyst.-The Cu-catalyzed addition of the title iodomethyl ketones (I) to olefins provides a new, efficient and general method for the synthesis of α,α-difluoro-functionalized ketones (III) (21 examples). Functional groups such as silyl, ester, acetal and ether remain unaffected. -(KWAK, K. C.; LEE, W.-Y.; ZHESHAN, Q.; LEE, Y. H.; YUN, Y.-G.; KWAK, G. B.; CHUNG, H.-T.; KWON, T.-O.; CHAI*, K. Y.; Bull. Korean Chem. Soc. 26 (2005) 1, 97-102; Dep. Bionanochem., Wonkwang Univ., Iksan 570-749, S. Korea; Eng.) -H. Toeppel 24-044

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The addition reactions of α,α-difluoroiodomethyl n-butyl ketone, α,α-difluoroiodomethyl cyclohexyl ketone, or α,α-difluoroiodomethyl phenyl ketone to alkenes were successfully accomplished in good yields in the presence of copper powder. The reaction was also applicable to alkenes containing a variety of functional groups such as ester, trimethylsilyl, or ether group. Acetonitrile was determined to be the best solvent in the present study and the reaction was performed at 55 o C for 15-22 h. This reaction provides a new, efficient and general method for the synthesis of α,α-difluoro functionalized ketones.