Cotelle N, Bernier J L, Hénichart J P, Catteau J P, Gaydou E, Wallet J C
Unité 16 INSERM, Lille, France.
Free Radic Biol Med. 1992 Sep;13(3):211-9. doi: 10.1016/0891-5849(92)90017-b.
To study the effect of the hydroxyl groups on biological activities of flavones, we synthesized 10 polyhydroxyflavones with varied substitution patterns. The abilities of the 10 compounds to act as radical scavengers were investigated using chemiluminescence in two biological models: the xanthine/xanthine oxidase system and the oxidative burst of rat alveolar macrophages. Stable radical formation was observed by electron spin resonance (ESR) spectroscopy. We found that the presence of the pyrogallol moiety in the B component of flavones gave rise to radical scavenger activity and that C-6 substituted hydroxyl group may also provide the basis for biological activity. Furthermore, compounds with a hydroxyl at C-7 position appeared to be xanthine oxidase inhibitors. One particular compound exhibited radical scavenger activity and xanthine oxidase inhibition. This type of compound should prove to be useful in the treatment of ischemia, for which both properties were required.
为研究羟基对黄酮类生物活性的影响，我们合成了10种具有不同取代模式的多羟基黄酮。利用化学发光法在两种生物学模型中研究了这10种化合物作为自由基清除剂的能力：黄嘌呤/黄嘌呤氧化酶系统和大鼠肺泡巨噬细胞的氧化爆发。通过电子自旋共振（ESR）光谱观察到稳定自由基的形成。我们发现黄酮类化合物B环中连苯三酚部分的存在产生了自由基清除活性，并且C-6位取代的羟基也可能为生物活性提供基础。此外，C-7位带有羟基的化合物似乎是黄嘌呤氧化酶抑制剂。一种特定的化合物表现出自由基清除活性和黄嘌呤氧化酶抑制作用。这类化合物在治疗缺血方面应该会被证明是有用的，因为缺血治疗需要这两种特性。
