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

The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C(3) unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C(3) side chain from the C(15) sesquiterpene, which arises f...

Descripción completa

Detalles Bibliográficos
Autores principales: Coca-Ruíz, Víctor, Suárez, Ivonne, Aleu, Josefina, Collado, Isidro G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Review
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8949605/
https://www.ncbi.nlm.nih.gov/pubmed/35336651
http://dx.doi.org/10.3390/plants11060769
_version_ 1784674937347244032
author Coca-Ruíz, Víctor
Suárez, Ivonne
Aleu, Josefina
Collado, Isidro G.
author_facet Coca-Ruíz, Víctor
Suárez, Ivonne
Aleu, Josefina
Collado, Isidro G.
author_sort Coca-Ruíz, Víctor
collection PubMed
description The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C(3) unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C(3) side chain from the C(15) sesquiterpene, which arises from farnesyl diphosphate (FDP). The C(12)-framework is generated, generally, in all families of sesquiterpenes by oxidative cleavage of the C(3) 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.
format Online
Article
Text
id pubmed-8949605
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-89496052022-03-26 Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites Coca-Ruíz, Víctor Suárez, Ivonne Aleu, Josefina Collado, Isidro G. Plants (Basel) Review The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C(3) unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C(3) side chain from the C(15) sesquiterpene, which arises from farnesyl diphosphate (FDP). The C(12)-framework is generated, generally, in all families of sesquiterpenes by oxidative cleavage of the C(3) 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. MDPI 2022-03-14 /pmc/articles/PMC8949605/ /pubmed/35336651 http://dx.doi.org/10.3390/plants11060769 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Coca-Ruíz, Víctor
Suárez, Ivonne
Aleu, Josefina
Collado, Isidro G.
Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title_full Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title_fullStr Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title_full_unstemmed Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title_short Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites
title_sort structures, occurrences and biosynthesis of 11,12,13-tri-nor-sesquiterpenes, an intriguing class of bioactive metabolites
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8949605/
https://www.ncbi.nlm.nih.gov/pubmed/35336651
http://dx.doi.org/10.3390/plants11060769
work_keys_str_mv AT cocaruizvictor structuresoccurrencesandbiosynthesisof111213trinorsesquiterpenesanintriguingclassofbioactivemetabolites
AT suarezivonne structuresoccurrencesandbiosynthesisof111213trinorsesquiterpenesanintriguingclassofbioactivemetabolites
AT aleujosefina structuresoccurrencesandbiosynthesisof111213trinorsesquiterpenesanintriguingclassofbioactivemetabolites
AT colladoisidrog structuresoccurrencesandbiosynthesisof111213trinorsesquiterpenesanintriguingclassofbioactivemetabolites

Ejemplares similares