Total synthesis and bioactivity of 18(R)-hydroxyeicosapentaenoic acid.
نویسندگان
چکیده
Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic acid via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.
منابع مشابه
Kojic acid-derived tyrosinase inhibitors: synthesis and bioactivity
Tyrosinase is a key enzyme for melanin biosynthesis, catalyzing the oxidation of L-tyrosine to L-dopaquinone. The tyrosinase inhibition is an effective approach to control hyperpigmentation in human skin and enzymatic browning in fruits and vegetables. Kojic acid is a naturally-occurring tyrosinase inhibitor which has been clinically used to treat the hyperpigmentation of skin. However, kojic a...
متن کاملUltrasonic Assisted Synthesis, Characterization and Bioactivity Assessment of Novel Piperonal Based Schiff Base and Its Metal Complexes
A novel Schiff base was synthesized by the reaction of piperonal and anthranilic acid, which was further utilized in the synthesis of five novel complexes by reaction with different metal salts ultrasonically. Time for the reaction was greatly reduced through ultrasound irradiations and the yield of reactions was also high as compared to the conventional methods using reflux conditions. The...
متن کاملMCM-41 functionalized sulfonic acid catalyzed one-pot synthesis of 1,8- dioxo-octahydroxanthenes
MCM-41-R-SO3H catalyzed one-pot synthesis of 1,8-dioxo-octahydroxanthenes is reportedunder reflux conditions. The catalyst is easily prepared, highly stable, very simple to handle andrecycled for five times without loss of significant activity
متن کاملSynthesis, Characterization, and Biological Activity Studies on Fanlizhicyclopeptide A
The synthesis of a proline-rich cyclic heptapeptide, fanlizhicyclopeptide A (8), previouslyisolated from the fruits of Annona squamosa (sugar-apples), is described via coupling oftetrapeptide l-prolyl-l-tyrosyl-l-leucyl-l-proline methyl ester with tripeptide Boc-glycyl-lvalyl-l-proline followed by cyclization of the linear fragment having seven amino acid units.Structure of the synthesized cycl...
متن کاملSynthesis, Characterization, and Biological Activity Studies on Fanlizhicyclopeptide A
The synthesis of a proline-rich cyclic heptapeptide, fanlizhicyclopeptide A (8), previouslyisolated from the fruits of Annona squamosa (sugar-apples), is described via coupling oftetrapeptide l-prolyl-l-tyrosyl-l-leucyl-l-proline methyl ester with tripeptide Boc-glycyl-lvalyl-l-proline followed by cyclization of the linear fragment having seven amino acid units.Structure of the synthesized cycl...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- The Journal of organic chemistry
دوره 76 13 شماره
صفحات -
تاریخ انتشار 2011