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

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

Víctor Coca-Ruíz  1 , Ivonne Suárez  1 , Josefina Aleu  1 , Isidro G Collado  1
Affiliations
Review

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

Víctor Coca-Ruíz et al. Plants (Basel). .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Molecular structure of 1(10),4-germacradiene.
Figure 2
Figure 2
Molecular structure of 11,12,13-tri-nor-germacranes and -elemanes.
Figure 3
Figure 3
Several isolated and characterized 11,12,13-tri-nor-eudesmanes-type sesquiterpenes.
Figure 4
Figure 4
Some 11,12,13-tri-nor-eudemanes.
Figure 5
Figure 5
Geosmin and derivatives.
Figure 6
Figure 6
Some isolated 11,12,13-tri-nor-eremophilanes.
Figure 7
Figure 7
Molecular structure of 11,12,13-tri-nor-eremophilane derivatives.
Figure 8
Figure 8
Molecular structure of 11,12,13-tri-nor-guaianes isolated and characterized.
Figure 9
Figure 9
Other 11,12,13-tri-nor-sesquiterpenes.
Figure 10
Figure 10
Proposed mechanism for biosynthesis of tri-nor-germacranes 2, 4 and 5, and tri-nor-elemanes 3, 7 and 8.
Figure 11
Figure 11
Proposed biosynthetic pathway to tri-nor-sesquiterpene by a special enzyme (adapted from Huang et al. 2010 [144]).
Figure 12
Figure 12
Biosynthesis of geosmin in M. xanthus and S. aurantiaca (adapted from Dickschat et al. 2005 [167]).
Figure 13
Figure 13
Biosynthesis of geosmin (28) in the liverwort Fossombronia pusilla.
Figure 14
Figure 14
Cyclization/fragmentation of FDP to Geosmin by geosmin synthase (adapted from Jiang and Cane 2008 [298]).
Figure 15
Figure 15
Proposed biosynthetic pathway to tri-nor-eremophilanes (adapted from Liu et al. 2016 [190]).
Figure 16
Figure 16
Hypothetical biosynthetic pathways of tri-nor-eremophilanes (adapted from Lin et al. 2021 [214]).
Figure 17
Figure 17
Incorporation of 13C from [2-13C]-labeled acetate into compounds 94, 95 and 106 (adapted from Takeda and Katoh 1983b [272]).
Figure 18
Figure 18
Hypothetical biogenetic pathway to clavukerins (adapted from Kobayashi et al. 1984b [241]).
Figure 19
Figure 19
Treatment of α-epoxyisoledene with TsOH.H2O in acetone yielding tri-nor-guiadiene.
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