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1 article(s) from Wüst, Matthias

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

Philipp P. Könen and
Matthias Wüst

Beilstein J. Org. Chem. 2019, 15, 1945–1961, doi:10.3762/bjoc.15.190

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Figure 1: Contour plot of a HS-SPME–GC×GC–TOF–MS chromatogram (TIC) demonstrating the separation of volatile ...

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Figure 2: Sesquiterpene hydrocarbons found in the headspace of Lemberger (Vitis vinifera subsp. vinifera, clo...

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Figure 3: Detailed part of the two-dimensional contour plot (Figure 1) to demonstrate the result of a successful feed...

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Scheme 1: First steps towards the formation of sesquiterpenes. The (S)-germacradienyl cation can be formed fr...

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Scheme 2: Possible biosynthetic pathways of the sesquiterpene hydrocarbons d₈-α-copaene, d₈-β-copaene, d₈-α-c...

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Scheme 3: Mechanistic rationale for the generation of the sesquiterpene hydrocarbons δ-cadinene (14), α-copae...

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Figure 4: MS spectra of genuine (d₀) and deuterium-labeled (d₆ and d₈) α-cubebene (left panel) after administ...

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Scheme 4: Putative formation pathways of the sesquiterpene hydrocarbons α-ylangene (5), β-ylangene (6), β-bou...

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Figure 5: MS spectra and expected labeling patterns of A: d₀-α-ylangene, B: d₈-α-ylangene after administratio...

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Figure 6: Expected labeling patterns of deuterium-labeled, aromatic sesquiterpenes after administration of [6...

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Figure 7: MS spectra and expected labeling patterns of genuine and deuterium-labeled A: calamenene (isomer) a...

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Figure 8: MS spectra and expected labeling patterns of genuine (d₀) and deuterium-labeled (d₉) β-elemene afte...

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Scheme 5: Possible biosynthesis of d₉-β-elemene, d₉-(+)-valencene and d₉-α-guaiene via germacrene A. *An inco...

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Scheme 6: Mechanistic rationale for the generation of the sesquiterpene hydrocarbons γ-elemene and selina-3,7...

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Figure 9: Mass spectra and associated structural formulas of d₀-γ-elemene and d₉-γ-elemene after administrati...

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Figure 10: MS spectra and expected labeling patterns of genuine (d₀) and deuterium-labeled (d₉) guaiazulene af...

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Scheme 7: Possible synthesis of d₉-guaiazulene, d₉-δ-elemene, d₉-guaia-6,9-diene and d₉-δ-selinene via germac...

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Scheme 8: Possible biosynthesis of d₆-(E)-β-caryophyllene and d₅-α-humulene starting from farnesyl pyrophosph...

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Figure 11: MS spectra and expected labeling patterns of d₀-(E)-β-caryophyllene and d₆-(E)-β-caryophyllene afte...

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Published 14 Aug 2019

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