Aroma von Rotweinbl�ten: Korrelation sensorischer Daten mit Headspace-Inhaltsstoffen

Buchbauer, Gerhard; Jirovetz, Leopold; Wasicky, Michael; Nikiforov, A.

doi:10.1007/bf01193255

Cited by 14 publications

(8 citation statements)

References 6 publications

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“…However, the sesquiterpene ketone rodundone was recently identified as the key odorant responsible for the peppery attributes of Australian Shiraz wines (Wood et al, 2008), which has led to a growing interest in this class of volatiles. Grapevine flowers produce several sesquiterpenoids with potential roles as attractants for pollinators (Buchbauer et al, 1994, Buchbauer et al, 1995; Lücker et al, 2004; Martin et al, 2009). Furthermore, several sesquiterpene hydrocarbons, most prominently a-ylangene, p-bourbonene, p-caryophyllene, a-humulene and germacrene D, and oxygenated sesquiterpenes, such as farnesol, nerolidol or y-eudesmol, have been described as grape berry and wine constituents (Alves et al, 2005;; Coelho et al, 2006; Robinson et al, 2011; Schreier et al, 1976).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

2013

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The participation of the mevalonic acid (MVA) and 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol-4-phosphate (DOXP/MEP) pathways in sesquiterpene biosynthesis of grape berries was investigated. There is an increasing interest in this class of terpenoids, since the oxygenated sesquiterpene rotundone was identified as the peppery aroma impact compound in Australian Shiraz wines. To investigate precursor supply pathway utilization, in vivo feeding experiments were performed with the deuterium labeled, pathway specific, precursors [5,5-2H2]-1-deoxy-D-xylulose and [5,5-2H2]-mevalonic acid lactone. Head Space-Solid Phase Micro Extraction-Gas Chromatography-Mass Spectrometry (HS-SPME-GC-MS) analysis of the generated volatile metabolites demonstrated that de novo sesquiterpene biosynthesis is mainly located in the grape berry exocarp (skin), with no detectable activity in the mesocarp (flesh) of the Lemberger variety. Interestingly, precursors from both the (primarily) cytosolic MVA and plastidial DOXP/MEP pathways were incorporated into grape sesquiterpenes in the varieties Lemberger, Gewürztraminer and Syrah. Our labeling data provide evidence for a homogenous, cytosolic pool of precursors for sesquiterpene biosynthesis, indicating that a transport of precursors occurs mostly from plastids to the cytosol. The labeling patterns of the sesquiterpene germacrene D were in agreement with a cyclization mechanism analogous to that of a previously cloned enantioselective (R)-germacrene D synthase from Solidago canadensis. This observation was subsequently confirmed by enantioselective GC-MS analysis demonstrating the exclusive presence of (R)-germacrene D, and not the (S)-enantiomer, in grape berries.

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Section: Introductionmentioning

confidence: 99%

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

2013

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“…Grapevine flowers produce numerous sesquiterpenoid volatiles [e.g. ( E )‐ β ‐caryophyllene, α ‐humulene, (+)‐valencene, ( E , E )‐ α ‐farnesene and (−)‐7‐epi‐ α ‐selinene] presumably as attractant for pollinators . In studies that were focused on the volatile profile of grapes and its development during ripening several sesquiterpenes, such as γ ‐elemene, α ‐ylangene, β ‐bourbonene and ( E )‐ β ‐caryophyllene, have been identified as natural constituents of grape berries .…”

Section: Introductionmentioning

confidence: 99%

“…(E)-b-caryophyllene, a-humulene, (+)-valencene, (E,E)-a-farnesene and (À)-7-epi-a-selinene] presumably as attractant for pollinators. [15][16][17] In studies that were focused on the volatile profile of grapes and its development during ripening several sesquiterpenes, such as g-elemene, a-ylangene, b-bourbonene and (E)-b-caryophyllene, have been identified as natural constituents of grape berries. [18,19] In addition, the induced biosynthesis of sesquiterpenes by methyl jasmonate was demonstrated in grape cell cultures and foliage of grapevine.…”

Section: Introductionmentioning

confidence: 99%

Temporal development of sesquiterpene hydrocarbon profiles of different grape varieties during ripening

May

Wüst

2012

Flavour & Fragrance J

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To investigate the profiles of sesquiterpene hydrocarbons in grape berries at different developmental stages several cultivars of Vitis vinifera (Gewürztraminer, Riesling, Yellow Muscat, Shiraz, Lemberger, Cabernet Sauvignon) were analysed during ripening. Therefore, HS‐SPME‐GC‐MS measurements were performed with intact grape berries. The measurements demonstrated that grapes emit numerous sesquiterpene hydrocarbons and that the sesquiterpene profile exhibits a characteristic profile, depending on the variety and the developmental stage. In particular, bicylic sesquiterpenes with a cadinane backbone increased during ripening, while acyclic sesquiterpenes such as (E,E)‐α‐farnesene decreased, except for Gewürztraminer which shows increasing amounts of acyclic sesquiterpenes towards harvest. Furthermore, the profiles of the emitted sesquiterpenes differed significantly. In particular, Gewürztraminer possessed remarkably high amounts of (E,E)‐α‐farnesene, (3E,6Z)‐α‐farnesene and (E,E)‐methylfarnesoate, while the sesquiterpene profiles of Riesling, Lemberger, Shiraz and Yellow Muscat were dominated by bi‐ and polycyclic sesquiterpenes. Cabernet Sauvignon showed only minor profile changes during ripening and its comparatively low sesquiterpene hydrocarbon amounts were dominated by (E)‐β‐caryophyllene, α‐humulene and an unidentified sesquiterpene. Copyright © 2012 John Wiley & Sons, Ltd.

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“…Grapevine flowers show the most significant expression of VviTPS genes, compared to other organs in the grapevine gene atlas (Fasoli et al, 2012). A concordant emission of terpenes has been observed in a limited number of cultivars profiled for their flower volatile emissions (Buchbauer et al, 1994a,b, 1995; Martin et al, 2009; Barbagallo et al, 2014; Matarese et al, 2014). These results clearly showed that grapevine flowers have a unique transcriptional and biosynthetic capacity to produce and emit terpenes, with the majority of cultivars emitting mainly sesquiterpenes, even though the biological/ecological role(s) for domesticated grapevine flower terpenes remain to be established.…”

Section: Introductionmentioning

confidence: 76%

Linking Terpene Synthases to Sesquiterpene Metabolism in Grapevine Flowers

2019

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Grapevine ( Vitis vinifera L.) terpene synthases (VviTPS) are responsible for the biosynthesis of terpenic volatiles. Volatile profiling of nine commercial wine cultivars showed unique cultivar-specific variation in volatile terpenes emitted from grapevine flowers. The flower chemotypes of three divergent cultivars, Muscat of Alexandria, Sauvignon Blanc and Shiraz were subsequently investigated at two flower developmental stages (EL-18 and -26). The cultivars displayed unique flower sesquiterpene compositions that changed during flower organogenesis and the profiles were dominated by either ( E )-β-farnesene, ( E,E )-α-farnesene or (+)-valencene. In silico remapping of microarray probes to VviTPS gene models allowed for a meta-analysis of VviTPS expression patterns in the grape gene atlas to identify genes that could regulate terpene biosynthesis in flowers. Selected sesquiterpene synthase genes were isolated and functionally characterized in three cultivars. Genotypic differences that could be linked to the function of a targeted gene model resulted in the isolation of a novel and cultivar-specific single product sesquiterpene synthase from Muscat of Alexandria flowers (VvivMATPS10), synthesizing ( E )-β-farnesene as its major volatile. Furthermore, we identified structural variations (SNPs, InDels and splice variations) in the characterized VviTPS genes that potentially impact enzyme function and/or volatile sesquiterpene production in a cultivar-specific manner.

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Aroma von Rotweinbl�ten: Korrelation sensorischer Daten mit Headspace-Inhaltsstoffen

Cited by 14 publications

References 6 publications

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

Temporal development of sesquiterpene hydrocarbon profiles of different grape varieties during ripening

Linking Terpene Synthases to Sesquiterpene Metabolism in Grapevine Flowers

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