Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids
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 iso...
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ftpubmed:oai:pubmedcentral.nih.gov:4770437 2023-05-15T16:49:23+02:00 Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids Warskulat, Anne‐Christin Tatsis, Evangelos C. Dudek, Bettina Kai, Marco Lorenz, Sybille Schneider, Bernd 2016-01-28 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770437/ http://www.ncbi.nlm.nih.gov/pubmed/26670055 https://doi.org/10.1002/cbic.201500572 en eng John Wiley and Sons Inc. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770437/ http://www.ncbi.nlm.nih.gov/pubmed/26670055 http://dx.doi.org/10.1002/cbic.201500572 © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. CC-BY-NC Full Papers Text 2016 ftpubmed https://doi.org/10.1002/cbic.201500572 2016-05-08T00:16:41Z 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. Text Iceland PubMed Central (PMC) ChemBioChem 17 4 318 327 |
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Full Papers Warskulat, Anne‐Christin Tatsis, Evangelos C. Dudek, Bettina Kai, Marco Lorenz, Sybille Schneider, Bernd Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
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Full Papers |
description |
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. |
format |
Text |
author |
Warskulat, Anne‐Christin Tatsis, Evangelos C. Dudek, Bettina Kai, Marco Lorenz, Sybille Schneider, Bernd |
author_facet |
Warskulat, Anne‐Christin Tatsis, Evangelos C. Dudek, Bettina Kai, Marco Lorenz, Sybille Schneider, Bernd |
author_sort |
Warskulat, Anne‐Christin |
title |
Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
title_short |
Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
title_full |
Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
title_fullStr |
Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
title_full_unstemmed |
Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids |
title_sort |
unprecedented utilization of pelargonidin and indole for the biosynthesis of plant indole alkaloids |
publisher |
John Wiley and Sons Inc. |
publishDate |
2016 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770437/ http://www.ncbi.nlm.nih.gov/pubmed/26670055 https://doi.org/10.1002/cbic.201500572 |
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Iceland |
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Iceland |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770437/ http://www.ncbi.nlm.nih.gov/pubmed/26670055 http://dx.doi.org/10.1002/cbic.201500572 |
op_rights |
© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
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CC-BY-NC |
op_doi |
https://doi.org/10.1002/cbic.201500572 |
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ChemBioChem |
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17 |
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4 |
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327 |
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1766039531610439680 |