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Biosynthesis of Nudicaulins: A 13 CO 2 ‐Pulse/Chase Labeling Study with Papaver nudicaule
Author(s) -
Tatsis Evangelos C.,
Eylert Eva,
Maddula Ravi Kumar,
Ostrozhenkova Elena,
Svatoš Aleš,
Eisenreich Wolfgang,
Schneider Bernd
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201402109
Subject(s) - biosynthesis , aglycone , petal , phenylpropanoid , chemistry , stereochemistry , isotopologue , indole test , biochemistry , biology , botany , glycoside , organic chemistry , molecule , enzyme
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 CO 2 ‐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 CO 2 ‐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 CO 2 ‐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.