[Establishment of Rapid Simultaneous Analysis Method for Plant Toxins by LC-TOF-MS].

Assuming food poisoning caused by toxic plants, an LC-TOF-MS-based method for the rapid and simultaneous analysis of 16 plant toxins was established. After adding water-methanol (1 : 9) and n-hexane, the samples were homogenized and extracted, and then subjected to centrifugal separation. Without any purification procedures, LC-TOF-MS measurements were performed, and qualitative and quantitative analyses using monoisotopic ion [M+H]+ (m/z) were conducted. The addition-recovery test using curry showed that qualitative analysis was possible under a setting with a retention time of ±0.2 minutes or less and mass accuracy of 5 ppm or lower and that quantitative analysis was possible with a recovery rate of 68-142% and a repeatability of 1.4-10.1%. Furthermore, measurements of the amount of plant toxins in the boiled plants and broths of cooked toxic plants demonstrated the transfer of plant toxins to broths. These suggest that in the event of food poisoning, broths may be used as an analysis sample, even when plants are not available.

Reductive SN 2' Reaction of Epoxydienoate with Borane and its Application to the Synthesis and Structural Revision of an Antitumor Active Torrubiellutin Analogue.

A reductive SN 2' reaction of epoxydienoates and epoxyenoates with borane was developed to afford skipped dienoates and unconjugated enoates with trisubstituted Z-alkene linked to asymmetric centers on one side or both sides. This reaction was successfully applied to the alternative synthesis of an antitumor active artificial analogue of torrubiellutin C. A geometric isomer for α,ß-unsaturated amide of the artificial analogue was also synthesized. These syntheses clarified the true structure of the antitumor active artificial analogue of torrubiellutin C.