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Iridoid Monoterpenes

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Abstract

At least 500 compounds (-300 iridoid glucosides, 100 sec-oiridoid glucosides, and 100 nonglycosidic iridoids) (Bowers, 1991; Croteau, 1981; Inouye, 1991; Inouye and Uesato, 1986), derived from a specialized monoterpenoid pathway and usually characterized by a 5-membered carbocyclic ring fused to a 6-membered heterocyclic ring containing an acetal linkage, are known (Fig. 20.1). Although the term iridoid is based on iridomyrmecin (1) and iridodial (2), two monoterpenes that occur in the defensive secretions of ants of the genus Iridomyrmex, most compounds of “iridoid” structure are found in plants. These compounds are frequently involved in plant-insect interactions and are sequestered, sometimes after modification, and apparently synthesized independently by some insects (Rimpler, 1991). In contrast to other monoterpenes, iridoid monoterpenes in plants are usually not associated with specialized oil glands or other such structures, and occur in all plant parts, typically as water-soluble glycosides, sometimes comprising several percent of the dry weight of the plant (Bowers, 1991; Stermitz, 1988). In some instances, up to 22–25% of plant materials may consist of iridoid compounds.

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Seigler, D.S. (1998). Iridoid Monoterpenes. In: Plant Secondary Metabolism. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4913-0_20

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