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Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation

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URI: http://hdl.handle.net/10498/20322

DOI: 10.1016/j.phytol.2015.05.020

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2015-Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation.pdf (431.3Kb)
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Author/s
Pérez, Andy J.; Simonet Morales, Ana MaríaAuthority UCA; Pecio, Lukasz; Kowalczyk, Mariusz; Calle, Juan M.; Oleszek, Wieslaw; Stochmal, Anna; Macías Domínguez, Francisco AntonioAuthority UCA
Date
2015-06
Department
Química Orgánica
Source
Phytochemistry Letters 13 (2015) 165–170
Abstract
Four triterpenoid saponins (1–4) were isolated from the aerial parts of Trifolium argutum Sol. (sharptooth clover) and their structures were elucidated by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Two of them are new compounds, characterized as 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyra- nosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (1) and 3-O-[β-D-galactopyranosyl-(1→2)- β-D-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (2). The occurrence of 3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (melilotigenin) in its natural form is reported for the first time as a triterpenoid aglycone within Trifolium species. The phytotoxicity of compounds was evaluated on four STS at concentration 1 μM to 333 mM. Compound 1 was the most active, showing more than 60% inhibition on the root growth of L. sativa at the higher dose, with IC50 (254.1 μM) lower than that of Logran1 (492.6 μM), a commercial herbicide used as positive control. The structure–activity relationships indicated that both aglycones and glycosidic parts may influence the phytotoxicity of saponins.
Subjects
Trifolium argutum Sol.; triterpenoid saponins; Structural elucidation; Phytotoxic activity; Structure–activity relationship
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  • Artículos Científicos INBIO [242]
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Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional

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