Stereoisomeric pattern of lilac aldehyde in Silene latifolia, a plant involved in a nursery pollination system

Dötterl, Stefan; Burkhardt, Dirk; Jürgens, Andreas; Mosandl, Armin

doi:10.1016/j.phytochem.2006.11.013

Cited by 16 publications

(15 citation statements)

References 31 publications

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“…In Syringa vulgaris L., it is known that lilac compounds are synthesized via the deoxy‐xylulose pathway, and linalool seems to be an important precursor (Kreck et al ., ). The same biosynthetic route has been proposed for other lilac aldehyde‐producing plants (Dötterl et al ., , ). Starting from linalool, which is enzymatically hydroxylated to 8‐hydroxylinalool, an oxidation step leads to 8‐oxolinalool, which is finally cyclized to the four (5′ R )‐configured and/or four (5′ S )‐configured lilac aldehyde stereoisomers (Kreck et al ., ).…”

Section: Discussionmentioning

confidence: 97%

Diel fragrance pattern correlates with olfactory preferences of diurnal and nocturnal flower visitors inSalix caprea(Salicaceae)

et al. 2014

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Floral scent, often a complex mixture of several volatile organic compounds (VOCs), has generally been interpreted as an adaptation to attract pollinators. However, not many studies have analysed which VOCs are functionally relevant for the reproductive success of a plant. Here, we show that, in Salix caprea (Salicaceae), temporal changes in floral scent emission during the day and night attract two different types of flower visitor: bees during the day and moths during the evening and night. We analysed the contribution of the two flower visitor groups to the reproductive success of the plant. The differences in scent emitted during the peak activity times of flower visitors (day versus night) were quantified and the response of 13 diurnal/nocturnal pollinator taxa to the floral scents was tested using gas chromatographic and electroantennographic techniques. Many of the c. 40 identified scent compounds were physiologically active, and bees and moths responded to nearly identical sets of compounds, although the response strengths differed. In bioassays, bees preferred the most abundant 1,4-dimethoxybenzene over lilac aldehyde, a compound with increased emission at night, whereas moths preferred lilac aldehyde over 1,4-dimethoxybenzene. Pollination by wind plus nocturnal pollinators (mainly moths) or by wind alone contributed less to seed set than pollination by wind plus diurnal pollinators (mainly bees). This suggests that the emission of scent during the night and attracting moths have no significant effect on reproductive success. It is possible that the emission of lilac aldehydes and other compounds at night is s result of phylogenetic constraints. Future studies should investigate whether moths may produce a marginal fitness gain in some years and/or some populations.

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Section: Discussionmentioning

confidence: 97%

Diel fragrance pattern correlates with olfactory preferences of diurnal and nocturnal flower visitors inSalix caprea(Salicaceae)

et al. 2014

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“…Bioassays with pure compounds further confirmed that preference for mutant flowers resulted from an attraction to linalool and from the lack of defensive volatiles and stored products (linalool oxides). It has been shown that lilac compounds are important in a specialized nursery pollination system for recognition by the noctuid moth nursery pollinator of white campion (Silene latifolia) (Dötterl et al, 2006b(Dötterl et al, , 2007. Moreover, lilac aldehydes from Asimitellaria were shown to induce the nectaring behavior of long-tongued fungus gnats but are repellent for short-tongued fungus gnats in olfactometer tests (Okamoto et al, 2015).…”

Section: Cyp76c1 Influences the Interactions Of Flowers With Insectsmentioning

confidence: 99%

CYP76C1 (Cytochrome P450)-Mediated Linalool Metabolism and the Formation of Volatile and Soluble Linalool Oxides in Arabidopsis Flowers: A Strategy for Defense against Floral Antagonists

Boachon¹,

Junker²,

Miesch³

et al. 2015

Plant Cell

144

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The acyclic monoterpene alcohol linalool is one of the most frequently encountered volatile compounds in floral scents. Various linalool oxides are usually emitted along with linalool, some of which are cyclic, such as the furanoid lilac compounds. Recent work has revealed the coexistence of two flower-expressed linalool synthases that produce the (S)-or (R)-linalool enantiomers and the involvement of two P450 enzymes in the linalool oxidation in the flowers of Arabidopsis thaliana. Partially redundant enzymes may also contribute to floral linalool metabolism. Here, we provide evidence that CYP76C1 is a multifunctional enzyme that catalyzes a cascade of oxidation reactions and is the major linalool metabolizing oxygenase in Arabidopsis flowers. Based on the activity of the recombinant enzyme and mutant analyses, we demonstrate its prominent role in the formation of most of the linalool oxides identified in vivo, both as volatiles and soluble conjugated compounds, including 8-hydroxy, 8-oxo, and 8-COOH-linalool, as well as lilac aldehydes and alcohols. Analysis of insect behavior on CYP76C1 mutants and in response to linalool and its oxygenated derivatives demonstrates that CYP76C1-dependent modulation of linalool emission and production of linalool oxides contribute to reduced floral attraction and favor protection against visitors and pests.

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“…Recently, the scent composition of S. latifolia and related species has been identified and studied for behavioral activity in the pollinators [4,10,14]. A large set of volatile compounds has been found in the S. latifolia floral odor bouquet [6,7,13,15] and these compounds comprise three major categories: fatty acid derivatives, aromatics, and terpenoids [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…Phenylacetaldehyde, one of the most abundant behaviorally active compounds, is involved in floral isolation of S. latifolia from the closely related species S. dioica [6]. These investigations altogether imply that veratrole, lilac aldehydes, and phenylacetaldehyde are key odor compounds that play a central role in pollinator attraction and floral isolation [6,7,10,14]. It is presently unclear which compounds induce oviposition by Hadena females into female S. latifolia flowers.…”

Section: Introductionmentioning

confidence: 99%

Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction

et al. 2012

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BackgroundSilene latifolia and its pollinator, the noctuid moth Hadena bicruris, represent an open nursery pollination system wherein floral volatiles, especially veratrole (1, 2-dimethoxybenzene), lilac aldehydes, and phenylacetaldehyde are of key importance for floral signaling. Despite the important role of floral scent in ensuring reproductive success in S. latifolia, the molecular basis of scent biosynthesis in this species has not yet been investigated.ResultsWe isolated two full-length cDNAs from S. latifolia that show similarity to rose orcinol O-methyltransferase. Biochemical analysis showed that both S. latifolia guaiacol O-methyltransferase1 (SlGOMT1) &S. latifolia guaiacol O-methyltransferase2 (SlGOMT2) encode proteins that catalyze the methylation of guaiacol to form veratrole. A large Km value difference between SlGOMT1 (~10 μM) and SlGOMT2 (~501 μM) resulted that SlGOMT1 is 31-fold more catalytically efficient than SlGOMT2. qRT-PCR expression analysis showed that the SlGOMT genes are specifically expressed in flowers and male S. latifolia flowers had 3- to 4-folds higher level of GOMT gene transcripts than female flower tissues. Two related cDNAs, S. dioica O-methyltransferase1 (SdOMT1) and S. dioica O-methyltransferase2 (SdOMT2), were also obtained from the sister species Silene dioica, but the proteins they encode did not methylate guaiacol, consistent with the lack of veratrole emission in the flowers of this species. Our evolutionary analysis uncovered that SlGOMT1 and SlGOMT2 genes evolved under positive selection, whereas SdOMT1 and SdOMT2 genes show no evidence for selection.ConclusionsAltogether, we report the identification and functional characterization of the gene, SlGOMT1 that efficiently catalyzes veratrole formation, whereas another copy of this gene with only one amino acid difference, SlGOMT2 was found to be less efficient for veratrole synthesis in S. latifolia.

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Stereoisomeric pattern of lilac aldehyde in Silene latifolia, a plant involved in a nursery pollination system

Cited by 16 publications

References 31 publications

Diel fragrance pattern correlates with olfactory preferences of diurnal and nocturnal flower visitors inSalix caprea(Salicaceae)

Diel fragrance pattern correlates with olfactory preferences of diurnal and nocturnal flower visitors inSalix caprea(Salicaceae)

CYP76C1 (Cytochrome P450)-Mediated Linalool Metabolism and the Formation of Volatile and Soluble Linalool Oxides in Arabidopsis Flowers: A Strategy for Defense against Floral Antagonists

Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction

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