Hill R H, Schurz H H, Posada de la Paz M, Abaitua Borda I, Philen R M, Kilbourne E M, Head S L, Bailey S L, Driskell W J, Barr J R
National Center for Environmental Health, Centers for Disease Control and Prevention (CDC), Atlanta, Georgia 30341-3724.
Arch Environ Contam Toxicol. 1995 Feb;28(2):259-64. doi: 10.1007/BF00217625.
The etiologic agent(s) that was responsible for the 1981 toxic oil syndrome [TOS] epidemic in Spain has not been identified. Liquid chromatography combined with atmospheric pressure ionization tandem mass spectrometry was used for the analysis of oils associated with TOS. Analyses focused on measuring 3-(N-phenylamino)-1,2-propanediol [PAP], the 3-oleyl ester of PAP [MEPAP], and the 1,2-di-oleyl ester of PAP [DEPAP]. DEPAP and MEPAP were found more frequently and at higher concentrations in TOS case-associated oils than in control oils with odds ratios of 13.7 (95% CI 5.0-38) and 21.9 (95% 6.1-78), respectively. Other fatty acid esters of PAP are also likely to be present in the TOS case-associated oils. More significantly, DEPAP and MEPAP were found in aniline-denatured rapeseed oil refined at ITH, the oil refining company with the clearest link to TOS cases, yet these PAP esters were not detected in unrefined aniline-denatured samples of rapeseed oil delivered to ITH. These results show that the esters of PAP were products of the ITH refining process and were not formed spontaneously during storage. PAP esters were not detected in samples of other aniline-denatured rapeseed oils that were refined elsewhere, and which were not associated with illness. These findings provide strong support for the hypothesis that one or more of the fatty acid esters of PAP were the etiologic agents for TOS.
导致1981年西班牙有毒食用油综合征（TOS）疫情的病原体尚未确定。采用液相色谱结合大气压电离串联质谱法对与TOS相关的油进行分析。分析重点是测量3-（N-苯基氨基）-1,2-丙二醇[PAP]、PAP的3-油酰酯[MEPAP]和PAP的1,2-二油酰酯[DEPAP]。与对照油相比，在与TOS病例相关的油中更频繁地发现DEPAP和MEPAP，且浓度更高，优势比分别为13.7（95%置信区间5.0-38）和21.9（95%置信区间6.1-78）。PAP的其他脂肪酸酯也可能存在于与TOS病例相关的油中。更重要的是，在ITH精炼的苯胺变性菜籽油中发现了DEPAP和MEPAP，ITH是与TOS病例联系最紧密的炼油公司，但在交付给ITH的未精炼苯胺变性菜籽油样品中未检测到这些PAP酯。这些结果表明，PAP酯是ITH精炼过程的产物，并非在储存过程中自发形成。在其他地方精炼且与疾病无关的其他苯胺变性菜籽油样品中未检测到PAP酯。这些发现为PAP的一种或多种脂肪酸酯是TOS病原体这一假说提供了有力支持。
