A NOMENCLATURE SYSTEM FOR THE ISOPROSTANES

In 1990, prostaglandin (PG) F-2-like compounds were discovered to be p roduced in abundance in vivo by a free radical mechanism independent o f the cyclooxygenase enzyme. Because these compounds are isomeric to c yclooxygenase-derived PGF(2 alpha), they were termed F-2-isoprostanes (F-2-IsoP's). Subsequently, it was also demonstrated that PGD(2)-like compounds (D-2-IsoP's) and PGE(2)-like compounds (E(2)-IsoP's) are als o produced in vivo as products of this pathway. Four different regiois omers of each of these classes of IsoP's are formed, each of which can be comprised of eight racemic diastereomers. Thus, 64 different F-2-I soP's, E(2)-IsoP's, and D-2-IsoP's can be formed. Interest in these mo lecules stems not only from the fact that quantification of IsoP's can provide a valuable index of free radical-induced lipid peroxidation i n vivo but also from the fact that it has bean shown that these compou nds are capable of exerting potent biological activity. Because of thi s potential for exerting biological activity, the chemical syntheses o f various IsoP compounds for biological testing has been initiated. As a result, a need for a systematic nomenclature for these compounds ha s evolved. A facile nomenclature that will allow rational differentiat ion and designation of each of the isomeric structures comprising the family of IsoP's is presented. (C) 1997 by Elsevier Science Inc.