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15‐Hydroperoxy‐PGE 2 : Intermediate in Mammalian and Algal Prostaglandin Biosynthesis
Author(s) -
Jagusch Hans,
Werner Markus,
Werz Oliver,
Pohnert Georg
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201910461
Subject(s) - biosynthesis , arachidonic acid , prostaglandin e , prostaglandin , metabolite , biochemistry , secondary metabolite , biology , algae , oxylipin , chemistry , enzyme , botany , gene
Arachidonic‐acid‐derived prostaglandins (PGs), specifically PGE 2 , play a central role in inflammation and numerous immunological reactions. The enzymes of PGE 2 biosynthesis are important pharmacological targets for anti‐inflammatory drugs. Besides mammals, certain edible marine algae possess a comprehensive repertoire of bioactive arachidonic‐acid‐derived oxylipins including PGs that may account for food poisoning. Described here is the analysis of PGE 2 biosynthesis in the red macroalga Gracilaria vermiculophylla that led to the identification of 15‐hydroperoxy‐PGE 2 , a novel precursor of PGE 2 and 15‐keto‐PGE 2 . Interestingly, this novel precursor is also produced in human macrophages where it represents a key metabolite in an alternative biosynthetic PGE 2 pathway in addition to the well‐established arachidonic acid‐PGG 2 ‐PGH 2 ‐PGE 2 route. This alternative pathway of mammalian PGE 2 biosynthesis may open novel opportunities to intervene with inflammation‐related diseases.