Carbon-Carbon Double Bond and Resorcinol in Resveratrol and Its Analogues: What Is the Characteristic Structure in Quenching Singlet Oxygen?

• Main Authors: Qingjun Kong, Xueyan Ren, Jianrui Qi, Jia Yu, Jun Lu, Shuo Wang
• Format: Article
• Language: English
• Published: MDPI AG 2019-07-01
• Series: Biomolecules
• Subjects: Resveratrol analogues; singlet-oxygen quencher; resorcinol; UHPLC-QTOF-MS²; UHPLC-QQQ-MS²; hydroxyl groups
• Online Access: https://www.mdpi.com/2218-273X/9/7/268

Stilbenes, particularly resveratrol and resveratrol dimers, could effectively quench singlet oxygen (¹O₂). It was reported that both resorcinol and carbon-carbon double bond quenching ¹O₂ can participate in the mechanism. However, it is still not clear which structure plays a dominant role in quenching ¹O₂. To investigate the characteristic structure in the mechanism of quenching ¹O₂, the resveratrol, pterostilbene and piceatannol quenching ¹O₂ abilities were compared by UHPLC-QTOF-MS² and UHPLC-QQQ-MS². Results showed that catechol, carbon-carbon double bond and resorcinol participated in the quenching of ¹O₂. Catechol ring plays a leading role in the mechanism, and the contribution of the structures in quenching ¹O₂ activity are as follows: catechol ring > carbon-carbon double bond > resorcinol ring, which is supported by the calculation of energy. Our findings will contribute to the future screening of stilbenes with higher activity, and those stilbenes may have great therapeutic potential in ¹O₂-mediated diseases.