NMR-guided isolation of undescribed triterpenoid saponins from Lysimachia atropurpurea L.

13,28-epoxyoleanane type saponins Lysimachia atropurpurea Myrsinaceae flavonoids myrsinoside B stralysaponins A-C

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
22 Apr 2024
Historique:
received: 04 12 2023
revised: 02 04 2024
accepted: 20 04 2024
medline: 25 4 2024
pubmed: 25 4 2024
entrez: 24 4 2024
Statut: aheadofprint

Résumé

Phytochemical investigation on aerial parts of Lysimachia atropurpurea L. (Myrsinaceae), guided by NMR methods, resulted in the isolation and characterization of three previously undescribed triterpenoid saponins named stralysaponins A-C along with five known compounds. Their structures were elucidated by 1D and 2D NMR spectroscopy and HR-ESI-MS. Stralysaponins A-C were categorized into 13β-28-epoxyoleanane-type triterpenoid saponins, reaffirming their prevalent presence of this type in the Myrsinaceae family and the genus Lysimachia. The identified derivatives share a common four-unit branched sugar chain, with rhamnose as the terminal sugar linked at C-3 of the aglycone. The presence of triterpenoid saponins in L. atropurpurea is reported herein for the first time. This study enriched the chemical diversity of triterpenoid saponins of the genus Lysimachia. Additionally, it demonstrates the effectiveness of NMR-profiling in isolating previously undescribed triterpenoid saponins from Lysimachia spp.

Identifiants

pubmed: 38657884
pii: S0031-9422(24)00141-9
doi: 10.1016/j.phytochem.2024.114104
pii:
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

114104

Informations de copyright

Copyright © 2024. Published by Elsevier Ltd.

Déclaration de conflit d'intérêts

Declaration of Competing Interest ☒ The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. ☐ The authors declare the following financial interests/personal relationships which may be considered as potential competing interests:

Auteurs

Stylianos Rallis (S)

Department of Pharmacognosy & Chemistry of Natural Products, School of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece.

Ekaterina-Michaela Tomou (EM)

Department of Pharmacognosy & Chemistry of Natural Products, School of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece. Electronic address: ktomou@pharm.uoa.gr.

Sofia K Drakopoulou (SK)

Laboratory of Analytical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.

Andreas G Tzakos (AG)

Department of Chemistry, Section of Organic Chemistry and Biochemistry, University of Ioannina, Ioannina, Greece.

Nikolaos S Thomaidis (NS)

Laboratory of Analytical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.

Helen Skaltsa (H)

Department of Pharmacognosy & Chemistry of Natural Products, School of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece. Electronic address: skaltsa@pharm.uoa.gr.

Classifications MeSH