title: Biosynthesis of Nudicaulins: A (13) CO2 -pulse/chase labeling study with Papaver nudicaule.
abstract: Nudicaulins are unique alkaloids responsible for the yellow color of the petals of some papaveraceaous plants. To elucidate the unknown biosynthetic origin of the skeleton, a (13) CO2 -pulse/chase experiment was performed with growing Papaver nudicaule plants. (13) C NMR analysis revealed more than 20 multiple (13) C-enriched isotopologues in nudicaulins from the petals of (13) CO2 -labeled plants. The complex labeling pattern was compared with the isotopologue composition of a kaempferol derivative that was isolated from petals of the same (13) CO2 -labeled plants. The deconvolution of the labeling profiles indicated that the nudicaulin scaffold is assembled from products or intermediates of indole metabolism, the phenylpropanoid pathway, and the polyketide biosynthesis. Naringenin-type compounds and tryptophan/tryptamine are potential substrates for the condensation reaction finally generating the aglycone skeleton of nudicaulins.
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.forename: Eva
authors.initials: E
authors.lastname: Eylert
authors.forename: Ravi Kumar
authors.initials: RK
authors.lastname: Maddula
authors.forename: Elena
authors.initials: E
authors.lastname: Ostrozhenkova
authors.forename: Aleš
authors.initials: A
authors.lastname: Svatoš
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Eisenreich
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry / Q000378:metabolism*; D002247:Carbon Isotopes; D007553:Isotope Labeling; D015394:Molecular Structure; D010207:Papaver / Q000737:chemistry / Q000254:growth & development / Q000378:metabolism*
chemical_list: D000470:Alkaloids; D002247:Carbon Isotopes; D002245:Carbon Dioxide
keywords: Papaver nudicaule; biosynthesis; indole alkaloids; isotopic labeling; nudicaulin