Biosynthesis of thiophenes in Tagetes patula.
The biosynthesis of 5-(3-buten-1-ynyl)-2,2'-bithiophene was studied in root cultures of Tagetes patula. Organ cultures were grown with [U-13C(6)]glucose or [1-13C]glucose. The bithiopene and amino acids from cell protein were isolated and analysed by quantitative NMR spectroscopy. Retrobiosynthetic analysis establish acetyl-CoA or a closely related compound (e.g. malonyl-CoA) as building blocks and their orientations in the bithiophene. The data confirm a previously suggested biosynthetic route via long-chain fatty acids and polyacetylenes. However, a polyketide-like biosynthesis via a carbocyclic intermediate cannot be excluded.
Margl
L
L
Biozentrum-Pharmazie, Universität Halle, Weinbergweg 22, D-06120, Halle/Saale, Germany.
Eisenreich
W
W
Adam
P
P
Bacher
A
A
Zenk
M H
MH
D019659:Asteraceae / Q000378:metabolism*; D002478:Cells, Cultured; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018517:Plant Roots / Q000166:cytology / Q000378:metabolism; D013876:Thiophenes / Q000737:chemistry / Q000378:metabolism*
D013876:Thiophenes; C097021:5-(3-buten-1-ynyl)-2,2'-bithiophene