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CC BY-NC-ND 4.0 · Planta Med 2024; 90(07/08): 641-650
DOI: 10.1055/a-2225-8314
Natural Product Chemistry and Analytical Studies
Original Papers

Structural Characterization, and Antioxidative and Anti-inflammatory Activities of Phylloxanthobilins in Tropaeolum majus, a Plant with Relevance in Phytomedicine[ # ]

Patricia Frei
1   Department of Pharmacy, Pharmaceutical Biology, Ludwig-Maximilian University of Munich, Germany
,
Christian Nadegger
2   Institute of Organic Chemistry, University of Innsbruck, Austria
,
Angelika M. Vollmar
1   Department of Pharmacy, Pharmaceutical Biology, Ludwig-Maximilian University of Munich, Germany
,
Thomas Müller
2   Institute of Organic Chemistry, University of Innsbruck, Austria
,
Simone Moser 
1   Department of Pharmacy, Pharmaceutical Biology, Ludwig-Maximilian University of Munich, Germany
3   Institute of Pharmacy, Department of Pharmacognosy, University of Innsbruck, Austria
› Author AffiliationsS. M. gratefully acknowledges funding from the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation; Project-ID 448289381).
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Abstract

Tropaeolum majus (garden nasturtium) is a plant with relevance in phytomedicine, appreciated not only for its pharmaceutical activities, but also for its beautiful leaves and flowers. Here, we investigated the phytochemical composition of senescent nasturtium leaves. Indeed, we identified yellow chlorophyll catabolites, also termed phylloxanthobilins, which we show to contribute to the bright yellow color of the leaves in the autumn season. Moreover, we isolated and characterized the phylloxanthobilins from T. majus, and report the identification of a pyro-phylloxanthobilin, so far only accessible by chemical synthesis. We show that the phylloxanthobilins contribute to bioactivities of T. majus by displaying strong anti-oxidative effects in vitro and in cellulo, and anti-inflammatory effects as assessed by COX-1 and COX-2 enzyme inhibition, similar to other bioactive ingredients of T. majus, isoquercitrin, and chlorogenic acid. Hence, phylloxanthobilins could play a role in the efficacy of T. majus in the treatment of urinary tract infections, an established indication of T. majus. With the results shown in this study, we aid in the completion of the phytochemical profile of T. majus by identifying additional bioactive natural products as relevant components of this medicinal plant.

Key words

Tropaeolum majus - Tropaeolaceae - antioxidant - anti-inflammatory properties - phylloxanthobilins - pyro-phyllobilin - phytochemicals

# This work is dedicated to Professors Rudolf Bauer, Chlodwig Franz, Brigitte Kopp, and Hermann Stuppner for their invaluable contributions and commitment to Austrian Pharmacognosy.


Supporting Information

    UV/Vis data and MS2 fragmentations of all PxBs as well as NMR spectra of Tm-PxB-1,-2,-4 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 28 June 2023

Accepted after revision: 28 November 2023

Article published online:
06 June 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commecial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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