TY - JOUR

T1 - Isotope-Guided Metabolomics Reveals Divergent Incorporation of Valine into Different Flavor Precursor Classes in Chives

AU - Freke, Ricarda

AU - Heinemann, Björn

AU - Hakim, Samuel Edward

AU - Witte, Claus Peter

AU - Herde, Marco

AU - Hildebrandt, Tatjana M.

AU - Franke, Jakob

N1 - Funding Information: We thank Alena Zinecker for initial work on this project. We like to acknowledge the support by the Deutsche Forschungsgemeinschaft (HE 5949/4‐1 to M.H.), and grant no. INST 187/741‐1 FUGG for support of the Orbitrap mass analyzer. J.F. gratefully acknowledges financial support by the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover, supported by the Ministry of Science and Culture (MWK) of Lower Saxony. Research in T.M.H.’s lab is funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence Strategy – EXC‐2048/1 – project ID 390686111. In addition, this work was supported by the LUH compute cluster, which is funded by the Leibniz Universität Hannover, the MWK, and the German Research Association (DFG). Figures 1–4 were created with BioRender.com. Open Access funding enabled and organized by Projekt DEAL.

PY - 2023/5/16

Y1 - 2023/5/16

N2 - Plants of the genus Allium such as chives, onions or garlic produce S-alk(en)yl cysteine sulfoxides as flavor precursors. Two major representatives are S-propenyl cysteine sulfoxide (isoalliin) and S-propyl cysteine sulfoxide (propiin), which only differ by a double bond in the C3 side chain. The propenyl group of isoalliin is derived from the amino acid valine, but the source of the propyl group of propiin remains unclear. Here, we present an untargeted metabolomics approach in seedlings of chives (Allium schoenoprasum) to track mass features containing sulfur and/or 13C from labeling experiments with valine-13C5 guided by their isotope signatures. Our data show that propiin and related propyl-bearing metabolites incorporate carbon derived from valine-13C5, but to a much lesser extent than isoalliin and related propenyl compounds. Our findings provide new insights into the biosynthetic pathways of flavor precursors in Allium species and open new avenues for future untargeted labeling experiments.

AB - Plants of the genus Allium such as chives, onions or garlic produce S-alk(en)yl cysteine sulfoxides as flavor precursors. Two major representatives are S-propenyl cysteine sulfoxide (isoalliin) and S-propyl cysteine sulfoxide (propiin), which only differ by a double bond in the C3 side chain. The propenyl group of isoalliin is derived from the amino acid valine, but the source of the propyl group of propiin remains unclear. Here, we present an untargeted metabolomics approach in seedlings of chives (Allium schoenoprasum) to track mass features containing sulfur and/or 13C from labeling experiments with valine-13C5 guided by their isotope signatures. Our data show that propiin and related propyl-bearing metabolites incorporate carbon derived from valine-13C5, but to a much lesser extent than isoalliin and related propenyl compounds. Our findings provide new insights into the biosynthetic pathways of flavor precursors in Allium species and open new avenues for future untargeted labeling experiments.

KW - Allium

KW - isoalliin

KW - isotope labeling

KW - propiin

KW - S-alk(en)yl cysteine sulfoxide

UR - http://www.scopus.com/inward/record.url?scp=85152799038&partnerID=8YFLogxK

U2 - 10.1002/cbic.202300056

DO - 10.1002/cbic.202300056

M3 - Article

C2 - 36853993

AN - SCOPUS:85152799038

VL - 24

JO - CHEMBIOCHEM

JF - CHEMBIOCHEM

SN - 1439-4227

IS - 10

M1 - e202300056

ER -