RT journal article
T1 Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation
A1 Pérez, Andy J.
A1 Simonet Morales, Ana María
A1 Pecio, Lukasz
A1 Kowalczyk, Mariusz
A1 Calle, Juan M.
A1 Oleszek, Wieslaw
A1 Stochmal, Anna
A1 Macías Domínguez, Francisco Antonio
A2 Química Orgánica
K1 Trifolium argutum Sol.
K1 triterpenoid saponins
K1 Structural elucidation
K1 Phytotoxic activity
K1 Structure–activity relationship
AB 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.
PB Phytochemistry Letters
YR 2015
FD 2015-06
LK http://hdl.handle.net/10498/20322
UL http://hdl.handle.net/10498/20322
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 05-nov-2026