Phytochemical Investigation of Rhus typhina Drupes and Identification of a New Antibacterial Lupane-Type Triterpenoid
- 1Laboratoire d’Analyse et de Séparation des Essences Végétales, Centre de Recherche sur la Boréalie, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, Saguenay, QC G7H 2B1, Canada
Abstract
The antibacterial constituents of Rhus typhina drupes remain poorly characterized despite their traditional medicinal use to treat infections. The methanolic extract of R. typhina drupes was evaluated for its antibacterial activity. It inhibited Escherichia coli (IC50 = 12 ± 1 µg/mL) and Staphylococcus aureus (IC50 = 33 ± 8 µg/mL). The extract was subjected to partial bioassay-guided fractionation and phytochemical investigation, leading to the isolation of eighteen compounds whose structures were elucidated by mass spectrometry and nuclear magnetic resonance spectroscopy. A new lupane-type triterpenoid, 3α-hydroxy-3β,25-epoxylup-20(29)-ene (1), was identified and characterized by high-resolution mass spectrometry, IR spectroscopy, and detailed 1D and 2D NMR analyses. HMBC and NOESY correlations supported a lupane-type skeleton bearing a ring-A hemiketal functionality and established its relative stereochemistry. Antibacterial activity was assessed against E. coli and S. aureus for the six isolated compounds available in sufficient quantities for testing. Compound 1 showed activity against S. aureus (IC50 of 0.052 ± 0.004 µM), while its cytotoxicity IC50 toward human WS-1 fibroblasts was >100 µM. Hyperoside (16) was also active against S. aureus (IC50 of 0.48 ± 0.09 µM). These results identify compound 1 as a candidate for further investigation of its antibacterial properties.
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BibTeX
@article{frissard2026phytochemical,
title = {{Phytochemical Investigation of Rhus typhina Drupes and Identification of a New Antibacterial Lupane-Type Triterpenoid}},
author = {Marie Frissard and Marianne Piochon and Jean Legault and Vakhtang Mshvildadze and Nassim Djabou and Jérôme Alsarraf and Antoine Desportes and Josianne Savard and André Pichette},
journal = {Molecules},
year = {2026},
month = nov,
doi = {10.3390/molecules31214012},
url = {https://www.mdpi.com/1420-3049/31/21/4012},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Phytochemical Investigation of Rhus typhina Drupes and Identification of a New Antibacterial Lupane-Type Triterpenoid
AU - Marie Frissard
AU - Marianne Piochon
AU - Jean Legault
AU - Vakhtang Mshvildadze
AU - Nassim Djabou
AU - Jérôme Alsarraf
AU - Antoine Desportes
AU - Josianne Savard
AU - André Pichette
PY - 2026
DA - 2026/11/06
JO - Molecules
DO - 10.3390/molecules31214012
UR - https://www.mdpi.com/1420-3049/31/21/4012
AB - The antibacterial constituents of Rhus typhina drupes remain poorly characterized despite their traditional medicinal use to treat infections. The methanolic extract of R. typhina drupes was evaluated for its antibacterial activity. It inhibited Escherichia coli (IC50 = 12 ± 1 µg/mL) and Staphylococcus aureus (IC50 = 33 ± 8 µg/mL). The extract was subjected to partial bioassay-guided fractionation and phytochemical investigation, leading to the isolation of eighteen compounds whose structures were elucidated by mass spectrometry and nuclear magnetic resonance spectroscopy. A new lupane-type triterpenoid, 3α-hydroxy-3β,25-epoxylup-20(29)-ene (1), was identified and characterized by high-resolution mass spectrometry, IR spectroscopy, and detailed 1D and 2D NMR analyses. HMBC and NOESY correlations supported a lupane-type skeleton bearing a ring-A hemiketal functionality and established its relative stereochemistry. Antibacterial activity was assessed against E. coli and S. aureus for the six isolated compounds available in sufficient quantities for testing. Compound 1 showed activity against S. aureus (IC50 of 0.052 ± 0.004 µM), while its cytotoxicity IC50 toward human WS-1 fibroblasts was >100 µM. Hyperoside (16) was also active against S. aureus (IC50 of 0.48 ± 0.09 µM). These results identify compound 1 as a candidate for further investigation of its antibacterial properties.
SN - 1420-3049
ER -