More lessons from linalool: insights gained from a ubiquitous floral volatile

Raguso, Robert A.

doi:10.1016/j.pbi.2016.05.007

Cited by 124 publications

(79 citation statements)

References 57 publications

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“…The linalool skeleton is characterized by double bonds and the C3 hydroxy group making it vulnerable to further modifications including derivatization (Raguso, 2016). The importance of C3 in linalool as a main contributor to odor quality has recently been shown (Elsharif et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

Metabolic Products of Linalool and Modulation of GABAA Receptors

et al. 2017

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Terpenoids are major subcomponents in aroma substances which harbor sedative physiological potential. We have demonstrated that various monoterpenoids such as the acyclic linalool enhance GABAergic currents in an allosteric manner in vitro upon overexpression of inhibitory α1β2 GABAA receptors in various expression systems. However, in plants or humans, i.e., following intake via inhalation or ingestion, linalool undergoes metabolic modifications including oxygenation and acetylation, which may affect the modulatory efficacy of the generated linalool derivatives. Here, we analyzed the modulatory potential of linalool derivatives at α1β2γ2 GABAA receptors upon transient overexpression. Following receptor expression control, electrophysiological recordings in a whole cell configuration were used to determine the chloride influx upon co-application of GABA EC10−30 together with the modulatory substance. Our results show that only oxygenated linalool metabolites at carbon 8 positively affect GABAergic currents whereas derivatives hydroxylated or carboxylated at carbon 8 were rather ineffective. Acetylated linalool derivatives resulted in non-significant changes of GABAergic currents. We can conclude that metabolism of linalool reduces its positive allosteric potential at GABAA receptors compared to the significant potentiation effects of the parent molecule linalool itself.

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Section: Discussionmentioning

confidence: 99%

Metabolic Products of Linalool and Modulation of GABAA Receptors

et al. 2017

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“…Considering the diverse interactions mediated by VOCs and their structural diversity, their functions may be highly specific. Interestingly, common VOCs, such as linalool, are also known to have multiple functions in different interaction systems (14).…”

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confidence: 99%

An unbiased approach elucidates variation in ( S )-(+)-linalool, a context-specific mediator of a tri-trophic interaction in wild tobacco

Fandino

Halitschke

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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Plant volatile organic compounds (VOCs) mediate many interactions, and the function of common VOCs is especially likely to depend on ecological context. We used a genetic mapping population of wild tobacco, Nicotiana attenuata, originating from a cross of 2 natural accessions from Arizona and Utah, separated by the Grand Canyon, to dissect genetic variation controlling VOCs. Herbivory-induced leaf terpenoid emissions varied substantially, while green leaf volatile emissions were similar. In a field experiment, only emissions of linalool, a common VOC, correlated significantly with predation of the herbivore Manduca sexta by native predators. Using quantitative trait locus mapping and genome mining, we identified an (S)-(+)-linalool synthase (NaLIS). Genome resequencing, gene cloning, and activity assays revealed that the presence/absence of a 766-bp sequence in NaLIS underlies the variation of linalool emissions in 26 natural accessions. We manipulated linalool emissions and composition by ectopically expressing linalool synthases for both enantiomers, (S)-(+)- and (R)-(−)-linalool, reported to oppositely affect M. sexta oviposition, in the Arizona and Utah accessions. We used these lines to test ovipositing moths in increasingly complex environments. The enantiomers had opposite effects on oviposition preference, but the magnitude of the effect depended strongly both on plant genetic background, and complexity of the bioassay environment. Our study reveals that the emission of linalool, a common VOC, differs by orders-of-magnitude among geographically interspersed conspecific plants due to allelic variation in a linalool synthase, and that the response of a specialist herbivore to linalool depends on enantiomer, plant genotype, and environmental complexity.

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“…For many flowering plants, floral scent is a key signal that attracts pollinators to transfer pollen, and hence is critical for their reproductive success (Raguso, 2008). Interestingly, many of the same volatile organic compounds are found both in floral volatiles and HIPVs, such as terpenoids (Tholl, 2006; Raguso et al ., 2016).…”

Section: Introductionmentioning

confidence: 99%

Allelic differences of clustered terpene synthases contribute to correlated intra-specific variation of floral and herbivory-induced volatiles in a wild tobacco

Xu¹,

Kreitzer²,

McGale³

et al. 2020

Preprint

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20• Plant volatile emissions can recruit predators of herbivores for indirect defence and 21 attract pollinators to aid in pollination. Although volatiles involved in defence and 22 pollinator attraction are primarily emitted from leaves and flowers, respectively, 23 they will co-evolve if their underlying genetic basis is intrinsically linked, either 24 due to pleiotropy or genetic linkage. However, direct evidence of co-evolving 25 defence and floral traits is scarce. 26• We characterized intra-specific variation of herbivory-induced plant volatiles 27 (HIPVs), the key components of indirect defence against herbivores, and floral 28 volatiles in the wild tobacco Nicotiana attenuata. 29• We found that variation of (E)-β-ocimene and (E)-α-bergamotene contributed to 30 the correlated changes in HIPVs and floral volatiles among N. attenuata natural 31 accessions. Intra-specific variations of (E)-β-ocimene and (E)-α-bergamotene 32 emissions resulted from allelic variation of two genetically co-localized terpene 33 synthase genes, NaTPS25 and NaTPS38 respectively. 34• Analyzing haplotypes of NaTPS25 and NaTPS38 revealed that allelic variations of 35NaTPS25 and NaTPS38 resulted in correlated changes of (E)-β-ocimene and (E)-α-36 bergamotene emission in HIPVs and floral volatiles in N. attenuata. 37• Together, these results provide evidence that pleiotropy and genetic linkage result 38 in correlated changes in defences and floral signals in natural populations, and the 39 evolution of plant volatiles is likely under diffuse selection. 40

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More lessons from linalool: insights gained from a ubiquitous floral volatile

Cited by 124 publications

References 57 publications

Metabolic Products of Linalool and Modulation of GABAA Receptors

Metabolic Products of Linalool and Modulation of GABAA Receptors

An unbiased approach elucidates variation in ( S )-(+)-linalool, a context-specific mediator of a tri-trophic interaction in wild tobacco

Allelic differences of clustered terpene synthases contribute to correlated intra-specific variation of floral and herbivory-induced volatiles in a wild tobacco

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