Table 1.
In vitro lipoxygenase (LOX) inhibitory activity at 0.01 µM or IC50 (µM). % Interaction with the stable radical 1,1-diphenyl-picrylhydrazyl (DPPH). Lipophilicity values: experimental RM and determination of lipophilicity as clog P.
| Compd. | Clog P a | RM b (±SD) c | LOX d,e IC50 (μM) (% Inhibition 100 µM) | RA% 50 µM 20 min | RA% 50 µM 60 min | RA% 100 µM 20 min | RA% 100 µM 60 min |
|---|---|---|---|---|---|---|---|
| 1i | 6.25 | −0.103 (0.009) | 100 | 38 | 37 | 44 | 46 |
| 1ii | 4.72 | −0.537 (0.002) | 91.5 | 40 | 39 | 45 | 47 |
| 2i | 7.00 | 0.605 (0.016) | 76.0 | 35 | 34 | 37 | 40 |
| 2ii | 5.47 | 0.061 (0.007) | 77.0 | 36 | 37 | 43 | 56 |
| 3i | 5.07 | 0.582 (0.037) | 7.4 | 34 | 37 | 48 | 51 |
| 3ii | 3.54 | −0.642 (0.032) | 89.0 | 43 | 35 | 44 | 46 |
| 4i | 5.40 | 0.423 (0.017) | 28% | 30 | 30 | 38 | 36 |
| 4ii | 3.87 | 0.011 (0.001) | 69.0 | 34 | 46 | 35 | 37 |
| 5i | 5.30 | 0.683 (0.015) | 77.5 | 33 | 33 | 36 | 38 |
| 5ii | 3.77 | −0.565 (0.003) | 81.5 | 32 | 39 | 30 | 41 |
| 6i | 7.33 | 0.480 (0.035) | 60.0 | 38 | 36 | 44 | 39 |
| 6ii | 5.80 | 0.622 (0.025) | 74.0 | 43 | 36 | 31 | 36 |
| 7i | 7.24 | 1.151 (0.021) | 72.5 | 34 | 35 | 30 | 31 |
| 7ii | 5.71 | 0.654 (0.016) | 57.5 | 33 | 35 | 33 | 34 |
| NDGA | - | - | 0.45 | 81 | 83 | 87 | 93 |
a Theoretically calculated clog P values; b RM values are the average of at least 5 measurements; c SD standard deviation <10%; d Soybean lipoxygenase inhibition expressed as IC50 (μM). IC50 represents the concentration of the tested compounds that is required for 50% inhibition in vitro. e Values are means (±SD < 10%) of three or four different determinations, (p = 0.05).