Millettia dubia De Wild. (Fabaceae): Structural analysis of the oleanane-type glycosides and stimulation of the sweet taste receptors TAS1R2/TAS1R3

From the root barks of a Central African tree Millettia dubia De Wild. (Fabaceae), ten previously undescribed oleanane-type glycosides were isolated by various chromatographic protocols. Their structures were elucidated by spectroscopic methods, mainly 2D NMR experiments and mass spectrometry, as mo...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2024-10, Vol.226, p.114204, Article 114204
Main Authors: Pertuit, David, Belloir, Christine, Bouizi, Younes, Delaude, Clément, Kapundu, Mpuza, Lacaille-Dubois, Marie-Aleth, Briand, Loïc, Mitaine-Offer, Anne-Claire
Format: Article
Language:English
Subjects:
2D NMR
agonists
Biochemistry, Molecular Biology
Chemical Sciences
chromatography
Fabaceae
Glycosides
Life Sciences
mass spectrometry
Millettia
Millettia dubia
Oleanolic acid
plant biochemistry
Sweet taste
sweetness
TAS1R2/TAS1R3
taste receptors
trees
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Summary:From the root barks of a Central African tree Millettia dubia De Wild. (Fabaceae), ten previously undescribed oleanane-type glycosides were isolated by various chromatographic protocols. Their structures were elucidated by spectroscopic methods, mainly 2D NMR experiments and mass spectrometry, as mono- and bidesmosidic glycosides of mesembryanthemoidigenic acid, hederagenin and oleanolic acid. The stimulation of the sweet taste receptor TAS1R2/TAS1R3 by these glycosides was evaluated, and structure/activity relationships were proposed. Two of them showed an agonist effect on TAS1R2/TAS1R3. [Display omitted] •Ten different oleanolic acid glycosides were isolated.•Their structures were elucidated by extensive 2D NMR analyses.•The stimulation of the sweet taste receptors TAS1R2/TAS1R3 was evaluated.•Some structure/activity relationships were discussed.
ISSN:0031-9422
1873-3700
1873-3700
0031-9422
DOI:10.1016/j.phytochem.2024.114204