Structures, Occurrences and Biosynthesis of 11,12,13-Tri- nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

Víctor Coca-Ruíz; Ivonne Suárez; Josefina Aleu; Isidro G Collado

doi:10.3390/plants11060769

Structures, Occurrences and Biosynthesis of 11,12,13-Tri- nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

Plants (Basel). 2022 Mar 14;11(6):769. doi: 10.3390/plants11060769.

Authors

Víctor Coca-Ruíz¹, Ivonne Suárez¹, Josefina Aleu¹, Isidro G Collado¹

Affiliation

¹ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, Spain.

Abstract

The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C₃ unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C₃ side chain from the C₁₅ sesquiterpene, which arises from farnesyl diphosphate (FDP). The C₁₂-framework is generated, generally, in all families of sesquiterpenes by oxidative cleavage of the C₃ substituent, with the simultaneous introduction of a double bond. This article reviews the isolation, biosynthesis and biological activity of this special class of sesquiterpenes, the 11,12,13-tri-nor-sesquiterpenes.

Keywords: 11,12,13-tri-nor-sesquiterpenes; biological activity; biosynthesis; isolation.

Publication types

Review