Evidence for the Biosynthetic Pathway from Sinapic Acid to Syringyl Lignin Using Labeled Sinapic Acid with Stable Isotope at Both Methoxy Groups in Robinia pseudoacacia and Nerium indicum

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Abstract
A tracer experiment using synthesized labeled lignin precursors was designed to confirm the actual biosynthetic pathway for syringyl lignin. Tetradeuteroferulic acid-[8-D, 3-OCD3] and heptadeuterosinapic acid-[8-D, 3,5-OCD3] were synthesized and fed to shoots of robinia (Robinia pseudoacacia) and oleander (Nerium indicum) trees. The incorporation of each labeled precursor into lignin was traced by gas chromatography−mass spectrometry. The synthesized sinapic acid, in which both methoxy groups were labeled, was useful in monitoring the conversion of sinapic acid into syringyl lignin. When heptadeuterosinapic acid was fed, syringyl units containing seven deuterium labels were detected. The results of this study support the traditionally accepted pathway that sinapic acid is converted to sinapyl alcohol via sinapoyl-CoA in robinia and oleander. Keywords: Lignin biosynthesis; heptadeutero sinapic acid-[8-D, 3,5-OCD3]; tracer experiments; sinapyl alcohol; robinia; oleander; 4-coumarate-CoA ligase (4CL)