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Lignin dimeric units are characterized by various inter-unit linkage types such as β-O-4, β-5, β-β, and β-1. Spirodienones are the native form of the β-1 structures, but the content in lignin has not been clarified. In this study, the ring-1- 13 C labeled coniferin was synthesized and administered to  Ginkgo biloba  shoots, obtaining ring-1 selectively labeled xylem samples. Enzymatically saccharified lignin (EL) samples were prepared from the xylem sample (400–600 µm distant region from the cambial zone), and solution-state quantitative  13 C NMR and solid-state CP/MAS NMR measurements were conducted. Acetylated EL (ELAc) was also prepared from the xylem sample (600–800 µm distant region from the cambial zone), and solution-state quantitative  13 C NMR and  1 H– 13 C 2D NMR measurements were conducted. Difference spectra obtained by subtracting the unlabeled spectra from the ring-1 labeled spectra showed that the ring-1 was responsible for broad signals at 134 ppm and signals of the spirodienone structure at 56.11 ppm (in solid-state), 54.70 ppm (EL in solution-state), and 54.72 ppm (ELAc in solution-state). The ratio of spirodienone structure was evaluated as 0.68 % (EL) and 0.72 % (ELAc) by the solution-state quantitative  13 C difference spectra, and 2.3 % (ELAc) by HSQC volume ratio of Cα′-H to G2-H.

Quantitative analysis of the β-1 structure in lignin by administration of [ring-1- 13 C]coniferin