Monks Terrence J, Jones Douglas C
Center for Molecular and Cellular Toxicology, Division of Pharmacology and Toxicology, College of Pharmacy, University of Texas at Austin, Austin, TX 78712-1074, USA.
Curr Drug Metab. 2002 Aug;3(4):425-38. doi: 10.2174/1389200023337388.
Quinones are ubiquitous in nature and constitute an important class of naturally occurring compounds found in plants, fungi and bacteria. Human exposure to quinones therefore occurs via the diet, but also clinically or via airborne pollutants. For example, the quinones of polycyclic aromatic hydrocarbons are prevalent as environmental contaminants and provide a major source of current human exposure to quinones. The inevitable human exposure to quinones, and the inherent reactivity of quinones, has stimulated substantial research on the chemistry and toxicology of these compounds. From a toxicological perspective, quinones possess two principal chemical properties that confer their reactivity in biological systems. Quinones are oxidants and electrophiles, and the relative contribution of these properties to quinone toxicity is influenced by chemical structure, in particular substituent effects. Modification to the quinone nucleus also influences quinone metabolism. This review will therefore focus on the differences in structure and metabolism of quinones, and how such differences influence quinone toxicology. Specific examples will be discussed to illustrate the diverse manner by which quinones interact with biological systems to initiate and propagate a toxic response.
醌类在自然界中广泛存在，是一类存在于植物、真菌和细菌中的重要天然化合物。因此，人类通过饮食接触醌类，但也会在临床环境中或通过空气污染物接触到醌类。例如，多环芳烃醌类作为环境污染物普遍存在，是当前人类接触醌类的主要来源。人类不可避免地会接触醌类，且醌类具有固有的反应活性，这激发了对这些化合物化学和毒理学的大量研究。从毒理学角度来看，醌类具有两种主要化学性质，使其在生物系统中具有反应活性。醌类是氧化剂和亲电试剂，这些性质对醌类毒性的相对贡献受化学结构影响，特别是取代基效应。对醌核的修饰也会影响醌类代谢。因此，本综述将重点关注醌类在结构和代谢方面的差异，以及这些差异如何影响醌类毒理学。将讨论具体实例，以说明醌类与生物系统相互作用引发和传播毒性反应的多种方式。
