Abstract
A phytochemical investigation of Polygala molluginifolia (root, stem, leaves and flowers) resulted in the isolation of four pyranoisoflavones, of which isoflavone 1 was previously unknown in the literature. Isoflavones 2-4: , although they are known synthetic compounds, are described in this work as new natural products. The isolated compounds were evaluated for their antioxidant effects and potential for inhibiting the acetylcholinesterase enzyme. Isoflavones 1 and 4 inhibited acetylcholinesterase, displaying IC50 values of 68 µmol L-1 and 84 µmol L-1, respectively. In the DPPH assay, the same compounds and rutin 5 exhibited EC50 values of 61 µmol L-1, 55 µmol L-1 and 16 µmol L-1, respectively. Moreover, the permeability of compounds 1-4: was evaluated using parallel artificial membrane permeability assay (PAMPA) with isoflavones 3 (9.25 × 10-6 cm s-1) and 4 (3.48 × 10-6 cm s-1) exhibiting the highest permeabilities.
Highlights
In the course of our research on the chemotaxonomy and biological activity of the genus Polygala, we investigated P. molluginifolia
P. cyparissias is used as a local anesthetic due to the presence of methyl salicylate in its roots,[12,13] and P. tenuifolia is used in traditional Chinese medicine to improve memory and intelligence.[14]
We report the isolation and structural elucidation of four isoflavones from P. molluginifolia, their antioxidant activity, acetylcholinesterase inhibition and parallel artificial membrane permeability assay (PAMPA) permeability
Summary
In the course of our research on the chemotaxonomy and biological activity of the genus Polygala, we investigated P. molluginifolia Soc. exhibits anti-depressant, anxiolytic and anti-convulsant activity.[21] We report the isolation and structural elucidation of four isoflavones from P. molluginifolia, their antioxidant activity, acetylcholinesterase inhibition and PAMPA (parallel artificial membrane permeability assay) permeability. Yellow solid; mp 205–207 °C; IR (KBr) υmax / cm-1 3416, 1654, 1595, 1507, 1452; UV (MeOH) λmax / nm (ε) 340 (2265), 302 (25604), 292 (25335), 258 (24798); for NMR data, see Table 1; HRMS (ESI+) m/z calculated for C25H22O6 [M+H]+: 419.1495; found, 419.1495.
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