New volatile sulfur-containing compounds from wild garlic (Allium ursinum L., Liliaceae)

• Allium ursinum L. (Liliaceae) is a popular substitute for garlic in many countries.
• New organosulfur compounds were found during an analysis of 12 A. ursinum samples.
• Their identification was based on GC–MS/NMR/IR and confirmed by synthesis and QSPR.
• The volatile profile of A. ursinum changed during plant material drying.

In many countries, the leaves of Allium ursinum L. (Liliaceae) are a popular substitute for garlic and, for centuries, the herb has been taken internally to treat an array of medical conditions. Herein, we report the chemical composition of 12 different A. ursinum essential-oil samples (five populations; fresh/air-/oven-dried plant material; leaves/inflorescences). GC–MS/GC–FID analyses, quantitative structure–property relationship modeling (simple 0D/1D-descriptors) of retention indices and the synthesis of selected compounds, enabled the identification of > 200 different constituents, mainly organo(poly)sulfides. Some of these were new compounds (allyl (methylthio)methyl, (methylthio)methyl (Z)/(E)-1-propenyl and allyl 1-(methylthio)propyl disulfides) or were previously not detected in samples of natural origin (heptyl methyl, methyl octyl, allyl hexyl (1), allyl octyl (2) and propyl (propylthio)methyl sulfides). A multivariate statistical analysis revealed the onset of significant changes in the plant material volatile profile during the drying process.

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