2. Academic Validation
  3. Lignans and sesquiterpene lactones from Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae)

Lignans and sesquiterpene lactones from Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae)

  • Phytochemistry. 2019 Sep;165:112047. doi: 10.1016/j.phytochem.2019.05.020.
Oleksandr Shulha 1,  Serhat Sezai Çiçek 1,  Helle Wangensteen 2,  Janina Kroes 3,  Malte Mäder 4,  Ulrich Girreser 4,  Jandirk Sendker 5,  Karin Jöhrer 6,  Richard Greil 7,  Wolfgang Schühly 8,  Alfonso Mangoni 9,  Laura Grauso 10,  Christoph van Thriel 3,  Christian Zidorn 11
Affiliations

Affiliations

  • 1 Pharmazeutisches Institut, Abteilung Pharmazeutische Biologie, Christian-Albrechts-Universität zu Kiel, Gutenbergstraße 76, 24118, Kiel, Germany.
  • 2 Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, 0316, Oslo, Norway.
  • 3 Leibniz-Institut für Arbeitsforschung, TU Dortmund, Ardeystraße 67, 44139, Dortmund, Germany.
  • 4 Pharmazeutisches Institut, Abteilung Pharmazeutische Chemie, Christian-Albrechts-Universität zu Kiel, Gutenbergstraße 76, 24118, Kiel, Germany.
  • 5 Institut für Pharmazeutische Biologie und Phytochemie, Universiät Münster, Corrensstraße 48, 48149, Münster, Germany.
  • 6 Tyrolean Cancer Research Institute, Innrain 66, 6020, Innsbruck, Austria.
  • 7 Tyrolean Cancer Research Institute, Innrain 66, 6020, Innsbruck, Austria; Paracelsus Medical University Salzburg, Department of Internal Medicine III, Laboratory for Immunological and Molecular Cancer Research, Müllner Hauptstraße 48, 5020, Salzburg, Austria.
  • 8 Institut für Zoologie, Universität Graz, Universitätsplatz 2/I, 8010, Graz, Austria.
  • 9 Dipartimento di Farmacia, Università di Napoli Federico II, Via Domenico Montesano 49, 80131, Napoli, Italy.
  • 10 Dipartimento di Agraria, Università di Napoli Federico II, Via Università 100, 80055, Portici (NA), Italy.
  • 11 Pharmazeutisches Institut, Abteilung Pharmazeutische Biologie, Christian-Albrechts-Universität zu Kiel, Gutenbergstraße 76, 24118, Kiel, Germany. Electronic address: czidorn@pharmazie.uni-kiel.de.
PMID: 31203102 DOI: 10.1016/j.phytochem.2019.05.020
Abstract

Four undescribed Lignans and two undescribed sesquiterpenic acids, together with three known compounds (hypochoeroside C, hypochoeroside D, and 5-O-caffeoylshikimic acid) were isolated from the roots of Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae). The Lignans were identified as 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranosyl-2'-O-methacrylate, (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one, and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid. The two sesquiterpenic acids were identified as the ring open precursors of hypochoerosides C and D. Structures were elucidated using NMR and HRMS. Absolute configurations of (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid were determined using electronic circular dichroism (ECD) spectroscopy. 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside was evaluated for its anti-proliferative activity against myeloma cell lines MM1S, U266, and NCI-H929 and showed cytotoxicity at 100 mM against MM1S strain. No neurotoxicity was observed for major compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, hypochoeroside C, and hypochoeroside D in a fluorescence assay measuring neurite outgrowth in dorsal root ganglion (DRG) neurons. Additionally, compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, hypochoeroside C, hypochoeroside D, and hypochoerosidic acid D were quantified in unstressed and drought-stressed Plants using HPLC-DAD. Drought-stressed Plants were found to contain lower concentrations of the lignan 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside and sesquiterpene lactone hypochoeroside C.

Keywords

Botanical systematics; Cytotoxicity; Hypochaeris radicata subsp. neapolitana, Asteraceae; Neurotoxicity; Phenylpropanoids; Sesquiterpenoids; Stringhalt.

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