Detection of new fumonisin mycotoxins and fumonisin-like compounds by reversed-phase high-performance liquid chromatography/electrospray ionization ion trap mass spectrometry

Detection of new fumonisin mycotoxins and fumonisin-like compounds by reversed-phase high-performance liquid chromatography/electrospray ionization ion trap mass spectrometry
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DOI:
10.1002/rcm.2607
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发表时间:
2006-01-01
影响因子:
2
通讯作者:
Bartok, Mihaly
Bartok, Mihaly
中科院分区:
化学3区
文献类型:
--
作者:
Bartok, Tibor;Szecsi, Arpad;Bartok, Mihaly

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伏马菌素产生于感染轮枝镰刀菌的水稻培养物中。为了降低伪影形成的可能性,在提取培养材料后立即通过反相高效液相色谱-电喷雾离子阱串联质谱法(RP-HPLC/ESI-IT-MS 2)分析伏马菌素,无需任何样品净化。除了已知的伏马菌素外,还检测到许多新的伏马菌素真菌毒素和伏马菌素样化合物。基于IT-MS 2数据,提出了不同系列伏马菌素的详细裂解途径,包括新的裂解机制。新化合物的保留时间、质子化分子和包括主链在内的产物离子的质量以及质子化分子的特征中性质量损失表明了它们的结构(应用众所周知的名称):iso-FA(1a,B)、iso-FB 1a-d、iso-FB 2,3a-e、PHFB 2a-c、PHFB 4a-d、FB 5/iso-FB 5a-d、FBK 1 2TCA、FBK 4 2TCA、FC 2、iso-FC 2,3、PHFC 4、FD和FBX系列。样品提取物中发现的伏马菌素和伏马菌素样化合物的相对量表示为FB 1的百分比(0.02-100%)。表示为FD的化合物的主链含有比具有C19或C20主链的公知伏马菌素更少的碳原子,并且很可能是较长化合物的前体。对于表示为FBX的化合物(12种化合物),连接到伏马菌素主链上的一个或两个OH基团被丙三羧酸以外的羧酸酯化,例如顺乌头酸、草酰琥珀酸和草酰富马酸。版权所有(c)2006约翰威利父子有限公司。
Fumonisins were produced in a rice culture infected with Fusarium verticillioides. To decrease the possibility of the formation of artifacts, the fumonisins were analyzed by reversed-phase high-performance liquid chromatography with electrospray ionization ion trap tandem mass spectrometry (RP-HPLC/ESI-IT-MS2) immediately after the extraction of the culture material without any sample clean-up. In addition to already known fumonisins, numerous new fumonisin mycotoxins and fumonisin-like compounds were detected. On the basis of the IT-MS2 data, detailed fragmentation pathways including new mechanisms were proposed for the different series of fumonisins. The retention times, the masses of the protonated molecules and of the product ions including the backbones and the characteristic neutral mass losses from the protonated molecules of the new compounds suggested their structures (applying the well-known designation): iso-FA(1a,b), iso-FB1a-d, iso-FB2,3a-e, PHFB2a-c, PHFB4a-d, FB5/iso-FB5a-d, FBK1 2TCA, FBK4 2TCA, FC2, iso-FC2,3, PHFC4, FD and FBX series. The relative quantities of fumonisins and fumonisin-like compounds found in the sample extract were expressed as percentages of FB1 (0.02-100%). The backbone of the compound denoted FD contained fewer carbon atoms than the well-known fumonisins with the C19 or C20 backbone and may well be a precursor of the longer compounds. For the compounds denoted FBX (12 compounds), one or two OH groups attached to the fumonisin backbone were esterified by carboxylic acids other than tricarballylic acid, such as cis-aconitic acid, oxalylsuccinic acid and oxalylfumaric acid. Copyright (c) 2006 John Wiley & Sons, Ltd.