(-)-2C-methyl-D-erythrono-1,4-lactone is formed after application of the terpenoid precursor 1-deoxy-D-xylulose.
Application of [1,2-14C]1-deoxy-D-xylulose, the committed precursor of terpenoids, thiamine and pyridoxol, to a variety of plant species resulted in the labelling of an unknown metabolite. The isolation and purification of this metabolite from Ipomoea purpurea plants fed with 1-deoxy-D-xylulose (DX), followed by NMR analysis, resulted in the identification of its structure as (-)-2C-methyl-D-erythrono-1,4-lactone (MDEL). MDEL has been previously isolated as a stress metabolite of certain plants. A hypothetical biosynthetic scheme is given.
Fellermeier
M A
MA
Institut für Pharmazie, Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Germany.
Maier
U H
UH
Sagner
S
S
Bacher
A
A
Zenk
M H
MH
D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D018520:Plant Shoots / Q000737:chemistry; D019657:Solanaceae / Q000378:metabolism; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*; D014996:Xylulose / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology
C115702:2C-methylerythrono-1,4-lactone; D007783:Lactones; D010936:Plant Extracts; D013729:Terpenes; D014996:Xylulose; C029724:1-deoxy-2-pentulose