Structural and biological diversity of cyclic octadecanoids, jasmonates, and mimetics

The jasmonate family of plant signaling compounds comprises biologically highly active cyclopentenones (for example, 12-oxo-phytodienoic acid) (12-OPDA) and cyclopentanones (for example, jasmonic acid) (JA) of related origin via the octadecanoid pathway, and structure. Among others, their biological activities include a broad range of defense-related reactions. Several lines of evidence indicate both common and different biological responses mediated by 12-OPDA and/or JA, suggesting the existence of at least two separate structure-activity groups. Based on the structure of a bacterial phytotoxin, coronatine, with similar biological activities compared with jasmonates, indanoyl isoleucine conjugates have been designed as functional synthetic mimics of octadecanoid-derived signals. The structural diversity of naturally occurring jasmonate-related compounds and synthetic mimics is discussed with respect to their corresponding biological activities. Novel strategies for the synthesis of various indanoyl isoleucine conjugates will be presented.