College of Food Science and Engineering, Shandong Agricultural University, Tai'an 271018, People's Republic of China.
J Agric Food Chem. 2012 Sep 12;60(36):9364-70. doi: 10.1021/jf302528e. Epub 2012 Aug 31.
The ozonolysis of aflatoxin B(1) (400 μg/mL) in acetonitrile solution was conducted with an ozone concentration of 6.28 mg/L at the flow rate of 60 mL/min for different times. The results showed that ozone was an effective detoxification agent because of its powerful oxidative role. Thin-layer chromatography and liquid chromatography-quadrupole time-of-flight mass spectra were applied to confirm and identify the ozonolysis products of aflatoxin B(1). A total of 13 products were identified, and 6 of them were main products. The structural identification of these products provided effective information for understanding the ozonolysis pathway of aflatoxin B(1). Two ozonolysis pathways were proposed on the basis of the accurate mass and molecular formulas of these product ions. Nine ozonolysis products came from the first oxidative pathway based on the Criegee mechanism, and the other four products were produced from the second pathway based on the oxidative and electrophilic reactions of ozone. According to the toxicity mechanism of aflatoxin B(1) to animals, the toxicity of aflatoxin B(1) was significantly reduced because of the disappearance of the double bond on the terminal furan ring or the lactone moiety on the benzene ring.
在流速为 60 毫升/分钟的条件下，用浓度为 6.28 毫克/升的臭氧对浓度为 400 μg/mL 的黄曲霉毒素 B(1)在乙腈溶液中进行臭氧化反应，反应时间不同。结果表明，臭氧是一种有效的解毒剂，因为它具有很强的氧化作用。采用薄层色谱和液相色谱-四极杆飞行时间质谱联用技术对黄曲霉毒素 B(1)的臭氧化产物进行了确证和鉴定。共鉴定出 13 种产物，其中 6 种为主要产物。这些产物的结构鉴定为了解黄曲霉毒素 B(1)的臭氧化途径提供了有效信息。基于这些产物离子的精确质量和分子式，提出了两种臭氧化途径。9 种臭氧化产物来自基于 Criegee 机理的第一个氧化途径，而另外 4 种产物则来自基于臭氧的氧化和亲电反应的第二个途径。根据黄曲霉毒素 B(1)对动物的毒性机制，由于末端呋喃环上的双键或苯环上的内酯部分的消失，黄曲霉毒素 B(1)的毒性显著降低。
