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. https://doi.org/10.3762/bjoc.15.190

Supporting Information

Supporting Information File 1: 3D view of signals from genuine and deuterated α-cubebene, α-ylangene and δ-elemene after feeding experiments using d3-MVL.
Format: PDF Size: 165.0 KB Download
Supporting Information File 2: Extracted ion chromatograms (EIC) of genuine (d0), partially labeled (d4, d6) and fully deuterium-labeled (d8) α-cubebene after administration of [6,6,6-2H3]-(±)-mevalonolactone (d3-MVL) to isolated exocarp of grape berries (Lemberger cultivar).
Format: PDF Size: 174.6 KB Download
Supporting Information File 3: Enlarged 2D chromatogram showing the separation of β-elemene, α-guaiene and β-ylangene.
Format: PDF Size: 174.5 KB Download
Supporting Information File 4: Putative formation pathway of d8-(E)-β-caryophyllene and d9-α-humulene starting from d9-farnesyl pyrophosphate.
Format: PDF Size: 204.2 KB Download

Cite the Following Article

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. https://doi.org/10.3762/bjoc.15.190

How to Cite

Könen, P. P.; Wüst, M. Beilstein J. Org. Chem. 2019, 15, 1945–1961. doi:10.3762/bjoc.15.190

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 1.4 MB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Yang, D.; Ma, D.; Song, Z.; Yang, M.; Xu, Y. The Composition, Antioxidant and Antibacterial Activity of Essential Oils from Five Species of the Magnoliaceae Family. Molecules (Basel, Switzerland) 2024, 29, 5182. doi:10.3390/molecules29215182
  • Alcântara Lemos, J. d.; Miranda, S. E. M.; Oliveira, M. L. G.; Cassali, G. D.; Ferreira, L. A. M.; Oliveira, A. E. M. d. F. M.; Barros, A. L. B. d. Sucupira oleoresin-based doxorubicin pH-sensitive nanoemulsions: A potential nanomedicine approach to enhance the safety profile and anticancer activity. Journal of Drug Delivery Science and Technology 2024, 101, 106317. doi:10.1016/j.jddst.2024.106317
  • Ishimoto, C. K.; Paulino, B. N.; Neri-Numa, I. A.; Bicas, J. L. The blue palette of life: A comprehensive review of natural bluish colorants with potential commercial applications. Food Research International 2024, 196, 115082. doi:10.1016/j.foodres.2024.115082
  • Fonseca, D.; Martins, N.; Garcia, R.; Cabrita, M. J. Comprehensive Two-Dimensional Gas Chromatography with a TOF MS Detector-An Effective Tool to Trace the Signature of Grape Varieties. Molecules (Basel, Switzerland) 2024, 29, 1989. doi:10.3390/molecules29091989
  • Mascrez, S.; Eggermont, D.; Purcaro, G. SPME and Chromatographic Fingerprints in Food Analysis. Evolution of Solid Phase Microextraction Technology; The Royal Society of Chemistry, 2023; pp 494–535. doi:10.1039/bk9781839167300-00494
  • Rodrigues, S.; Fernandes, F. A. N. Effect of Dielectric Barrier Discharge Plasma Treatment in Pasteurized Orange Juice: Changes in Volatile Composition, Aroma, and Mitigation of Off-flavors. Food and Bioprocess Technology 2022, 16, 930–939. doi:10.1007/s11947-022-02976-0
  • Rodrigues, S.; Fernandes, F. A. N. Glow Discharge Plasma Processing for the Improvement of Pasteurized Orange Juice's Aroma and Off-Flavor. Processes 2022, 10, 1812. doi:10.3390/pr10091812
  • Naundrup, A.; Bohman, B.; Kwadha, C. A.; Jensen, A. B.; Becher, P. G.; De Fine Licht, H. H. Pathogenic fungus uses volatiles to entice male flies into fatal matings with infected female cadavers. The ISME journal 2022, 16, 2388–2397. doi:10.1038/s41396-022-01284-x
  • Ďurkovič, J.; Bubeníková, T.; Gužmerová, A.; Fleischer, P.; Kurjak, D.; Čaňová, I.; Lukáčik, I.; Dvořák, M.; Milenković, I. Effects of Phytophthora Inoculations on Photosynthetic Behaviour and Induced Defence Responses of Plant Volatiles in Field-Grown Hybrid Poplar Tolerant to Bark Canker Disease. Journal of fungi (Basel, Switzerland) 2021, 7, 969. doi:10.3390/jof7110969
  • Naundrup, A.; Bohman, B.; Kwadha, C. A.; Jensen, A. R.; Becher, P. G.; De Fine Licht, H. H. A pathogenic fungus uses volatiles to entice male flies into fatal matings with infected female cadavers. Cold Spring Harbor Laboratory 2021. doi:10.1101/2021.10.21.465334
  • Könen, P. P.; Stötzel, I.; Schwab, W.; Wüst, M. Qualitative profiling of mono- and sesquiterpenols in aglycon libraries from Vitis vinifera L. Gewürztraminer using multidimensional gas chromatography–mass spectrometry. European Food Research and Technology 2021, 247, 1117–1124. doi:10.1007/s00217-021-03692-3
  • Könen, P. P.; Wüst, M.; Passon, M. Comprehensive Foodomics - Crop Metabolome Analysis – In Vivo-Labeling With Stable Isotopes for Specific Metabolite Profiling. Comprehensive Foodomics; Elsevier, 2021; pp 105–115. doi:10.1016/b978-0-08-100596-5.22781-9
  • Welke, J. E.; Hernandes, K. C.; Nicolli, K. P.; Barbará, J. A.; Biasoto, A. C. T.; Zini, C. A. Role of gas chromatography and olfactometry to understand the wine aroma: Achievements denoted by multidimensional analysis. Journal of separation science 2020, 44, 135–168. doi:10.1002/jssc.202000813
  • Könen, P. P.; Wüst, M. Dissecting Sesquiterpene Profiles of Lemberger Red Wines Using Ex Vivo Tissue Deuterium-Labeling and Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight-Mass Spectrometry. Journal of agricultural and food chemistry 2020, 68, 8936–8941. doi:10.1021/acs.jafc.0c03273
  • Campelo, P. H.; Filho, E. G. A.; Silva, L. M. A.; de Brito, E. S.; Rodrigues, S.; Fernandes, F. A. Modulation of aroma and flavor using dielectric barrier discharge plasma technology in a juice rich in terpenes and sesquiterpenes. LWT 2020, 130, 109644. doi:10.1016/j.lwt.2020.109644
  • Campelo, P. H.; Filho, E. G. A.; Silva, L. M. A.; de Brito, E. S.; Rodrigues, S.; Fernandes, F. A. Modulation of aroma and flavor using glow discharge plasma technology. Innovative Food Science & Emerging Technologies 2020, 62, 102363. doi:10.1016/j.ifset.2020.102363
  • Caffrey, A.; Lerno, L. A.; Zweigenbaum, J.; Ebeler, S. E. Direct Analysis of Glycosidic Aroma Precursors Containing Multiple Aglycone Classes in Vitis vinifera Berries. Journal of agricultural and food chemistry 2020, 68, 3817–3833. doi:10.1021/acs.jafc.9b08323
  • Amaral, M. S.; Nolvachai, Y.; Marriott, P. J. Comprehensive Two-Dimensional Gas Chromatography Advances in Technology and Applications: Biennial Update. Analytical chemistry 2019, 92, 85–104. doi:10.1021/acs.analchem.9b05412
  • Dickschat, J. S.; Celik, E.; Brock, N. L. Volatiles from three genome sequenced fungi from the genus Aspergillus. Beilstein journal of organic chemistry 2018, 14, 900–910. doi:10.3762/bjoc.14.77
Other Beilstein-Institut Open Science Activities