4′-Hydroxy-6,7-methylenedioxy-3-methoxyflavone: A novel flavonoid from Dulacia egleri with potential inhibitory activity against cathepsins B and L

A new flavone, 4′-hydroxy-6,7-methylenedioxy-3-methoxyflavone 1, and two other nucleosides, ribavirin 2 and adenosine 3, were isolated from the leaves of Dulacia egleri. The nucleosides were identified by spectroscopic techniques (1D, 2D-NMR) while the structure of the flavonoid was established by 1D, 2D-NMR analysis, including HRESIMS data. The results obtained in the biological assays showed that the compound 1 was able to inhibit cathepsins B and L with IC50 of 14.88 ± 0.18 μM and 3.19 ± 0.07 μM, respectively. The mechanism of inhibition for both enzymes were determined showing to be competitive at cathepsin B with Ki = 12.8 ± 0.6 μM and non-linear non-competitive with positive cooperativity inhibition at cathepsin L with Ki = 322 ± 33 μM, αKi = 133 ± 15 μM, βKi = 5.14 ± 0.41 μM and γKi = 13.2 ± 13 μM. [Display omitted]