title: Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids.
abstract: Nudicaulins are a group of indole alkaloid glycosides responsible for the color of yellow petals of Papaver nudicaule (Iceland poppy). The unique aglycone scaffold of these alkaloids attracted our interest as one of the most unusual flavonoid-indole hybrid structures that occur in nature. Stable isotope labeling experiments with sliced petals identified free indole, but not tryptamine or l-tryptophan, as one of the two key biosynthetic precursors of the nudicaulin aglycone. Pelargonidin was identified as the second key precursor, contributing the polyphenolic unit to the nudicaulin molecule. This finding was inferred from the temporary accumulation of pelargonidin glycosides in the petals during flower bud development and a drop at the point in time when nudicaulin levels start to increase. The precursor-directed incorporation of cyanidin into a new 3'-hydroxynudicaulin strongly supports the hypothesis that anthocyanins are involved in the biosynthesis of nudicaulins.
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany.
authors.forename: Anne-Christin
authors.initials: AC
authors.lastname: Warskulat
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany.
authors.forename: Evangelos C
authors.initials: EC
authors.lastname: Tatsis
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany.
authors.forename: Bettina
authors.initials: B
authors.lastname: Dudek
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany.
authors.forename: Marco
authors.initials: M
authors.lastname: Kai
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany.
authors.forename: Sybille
authors.initials: S
authors.lastname: Lorenz
authors.affiliation: Max Planck Institut für chemische Ökologie, Hans Knöll Strasse 8, 07745, Jena, Germany. schneider@ice.mpg.de.
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000378:metabolism*; D000872:Anthocyanins / Q000737:chemistry / Q000378:metabolism*; D053898:Biosynthetic Pathways; D026121:Indole Alkaloids / Q000737:chemistry / Q000378:metabolism*; D010207:Papaver / Q000737:chemistry / Q000378:metabolism*; D061065:Polyketides / Q000737:chemistry / Q000378:metabolism
chemical_list: D000470:Alkaloids; D000872:Anthocyanins; D026121:Indole Alkaloids; D061065:Polyketides; C066957:pelargonidin
keywords: biosynthesis; indole alkaloids; isotopic labeling; natural products; nudicaulins