A biosynthetic pathway for (
E
)-methyl cinnamate formation was evaluated in Tricholoma matsutake by tracer experiments using 13C- and 2H-labeled precursors. One hundred percent selective 13C incorporation was observed when L-[1,2,3
,4
,5,6,7
,8
,9
-13C9
, 15/N]phenylalanine was converted to (E
)-[1,2,3
,4
,5,6,7
,8
,9
-13C9
]cinnamate and (E
)-[1,2,3
,4
,5,6,7
,8
,9
-13C9
]methyl cinnamate. Similarly, 100% selective 13C incorporation was observed when (E
)-[1,2,3
,4
,5,6,7
,8
,9
-13C9
]cinnamate was converted to (E
)-[1,2,3
,4
,5,6,7
,8
,9
-13C9
]methyl cinnamate. In contrast, the 2H incorporation selectivities were 82
.1% and 81
.4
% when L-[2,3
,4
,5,6,7
,7
,8
-2H8
]phenylalanine was converted to (E
)-[2,3
,4
,5,6,7
,8
-2H7
]cinnamate and (E
)-[2,3
,4
,5,6,7
,8
-2H7
]methyl cinnamate, respectively. Thus, T. matsutake synthesizes (E
)-methyl cinnamate from L-phenylalanine via (E
)-cinnamate. (E
)-cinnamate was likely formed through two pathways: one was major and the other was a minor.
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