氧杂蒽酮衍生物的抗氧化活性

ANTIOXIDANT ACTIVITY OF XANTHONE DERIVATIVES.

作者信息

Francik Renata, Szkaradek Natalia, Zelaszczyk Dorota, Marona Henryk

出版信息

Acta Pol Pharm. 2016 Nov;73(6):1505-1509.

Abstract

Certain xanthone derivatives, such as these present in mangosteen fruits, show strong antioxidant activity. On the other hand, evidences accumulated that oxidative stress is involved in epileptogenesis. Therefore, the aim of the present study was to estimate total antioxidant capacity (expressed as a ferric reducing antioxidant power - FRAP) and evaluate ability to scavenge free radicals (DPPH methods) by xanthone derivatives showing antiepileptic activity. Selected 2-(aminomethyl)-9H-xanthen-9-one derivatives shared structural features, such as chlorine substituent in xanthone ring and different chiral (or not) alkanol groups at the nitrogen atom. The results of antioxidant activities among racemates revealed the highest activity for compound (RIS)-3 (31.7% in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and (0.184 ± 0.003 mM Fe²⁺/L) in FRAP assay. Among tested pair of enantiomers we observed that (R)-1 and (R)-2 showed higher reduction capacity ((R)-1: 0.096 ± 0.007 mM F²⁺/L; (R)-2: 0.048 ± 0.005 mM Fe²⁺/L, respectively) and stronger DPPH scavenging activity ((R)-1: 31 ± 3.0%; (R)-2: 29 ± 2.5%, respectively) comparing to their (S)-enantiomers and racemates.

摘要

某些氧杂蒽衍生物，比如山竹果中含有的这些衍生物，具有很强的抗氧化活性。另一方面，越来越多的证据表明氧化应激参与癫痫发生过程。因此，本研究的目的是评估具有抗癫痫活性的氧杂蒽衍生物的总抗氧化能力（以铁还原抗氧化能力——FRAP表示），并评价其清除自由基的能力（DPPH法）。所选的2-(氨甲基)-9H-呫吨-9-酮衍生物具有共同的结构特征，比如氧杂蒽环上的氯取代基以及氮原子上不同的手性（或非手性）链烷醇基团。外消旋体的抗氧化活性结果显示化合物(RIS)-3的活性最高（在二苯基-2-苦基肼基（DPPH）自由基清除试验中为31.7%，在FRAP测定中为(0.184±0.003 mM Fe²⁺/L)）。在测试的对映体对中，我们观察到(R)-1和(R)-2与它们的(S)-对映体和外消旋体相比，具有更高的还原能力（(R)-1：0.096±0.007 mM F²⁺/L；(R)-2：0.048±0.005 mM Fe²⁺/L）和更强的DPPH清除活性（(R)-1：31±3.0%；(R)-2：29±2.5%）。