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Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called “yellow twig” Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (...

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Autores principales: Songoen, Weerasak, Brunmair, Julia, Traxler, Florian, Wieser, Viktoria Chiara, Phanchai, Witthawat, Pluempanupat, Wanchai, Brecker, Lothar, Schinnerl, Johann
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414341/
https://www.ncbi.nlm.nih.gov/pubmed/36014416
http://dx.doi.org/10.3390/molecules27165176
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author Songoen, Weerasak
Brunmair, Julia
Traxler, Florian
Wieser, Viktoria Chiara
Phanchai, Witthawat
Pluempanupat, Wanchai
Brecker, Lothar
Schinnerl, Johann
author_facet Songoen, Weerasak
Brunmair, Julia
Traxler, Florian
Wieser, Viktoria Chiara
Phanchai, Witthawat
Pluempanupat, Wanchai
Brecker, Lothar
Schinnerl, Johann
author_sort Songoen, Weerasak
collection PubMed
description Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called “yellow twig” Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a (1)H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants’ defense strategy.
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spelling pubmed-94143412022-08-27 Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species Songoen, Weerasak Brunmair, Julia Traxler, Florian Wieser, Viktoria Chiara Phanchai, Witthawat Pluempanupat, Wanchai Brecker, Lothar Schinnerl, Johann Molecules Article Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called “yellow twig” Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a (1)H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants’ defense strategy. MDPI 2022-08-14 /pmc/articles/PMC9414341/ /pubmed/36014416 http://dx.doi.org/10.3390/molecules27165176 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Songoen, Weerasak
Brunmair, Julia
Traxler, Florian
Wieser, Viktoria Chiara
Phanchai, Witthawat
Pluempanupat, Wanchai
Brecker, Lothar
Schinnerl, Johann
Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title_full Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title_fullStr Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title_full_unstemmed Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title_short Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species
title_sort yellow twig (nauclea orientalis) from thailand: strictosamide as the key alkaloid of this plant species
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414341/
https://www.ncbi.nlm.nih.gov/pubmed/36014416
http://dx.doi.org/10.3390/molecules27165176
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