Clinical Toxicology. Biomass Component Extraction: The uneaten cooked plant specimen was prepared for

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1 Clinical Toxicology Page of 0 Materials and Methods Biomass Component Extraction: The uneaten cooked plant specimen was prepared for chemical analysis as follows. The sample was frozen, diced, pulverized and lyophilized. Ten milliliters of % ethanol was added to g dried biomass and vortexed. The resulting slurry was sonicated for one hour followed by overnight shaking. The extract was purified by solid phase extraction (SPE) C column conditioned with methanol and water. Plant components were eluted with ethanol, and dried under a stream of nitrogen. The solid extract was re-dissolved in ethanol for chemical characterization. Sample Preparation: ml aliquots of patient samples were diluted with ml deionized water and passed through supported liquid extraction (SLE) columns (SLE+ columns, Isolute ) using -0. bar of applied pressure for - seconds. Following a five-minute absorption period, ml of chloroform was added and allowed to flow for minutes under gravity. The elution was completed by applied vacuum of -0. bar for 0 seconds. The solvent was evaporated under a stream of nitrogen and samples were dissolved in 00 µl of ethanol. LC-MS Analysis: Chromatographic separation of samples was carried out using a Dionex Ultimate 00 HPLC system with a mobile phase gradient of 0.% formic acid and % acetonitrile in aqueous solvent (solvent A) and 0.% formic acid in acetonitrile (solvent B) with a Thermo Acclaim 0 C column (. mm, µm). Solvent A was initially 0%, and Solvent B increased to % over a min linear gradient, with a min total run time and a flow rate of 00 µl/min. The injection volume was µl

2 Page of Clinical Toxicology 0 for all samples except µl for the plant extract. Analysis of samples was performed using high resolution Bruker Daltonics maxis Quadrupole Time-of-Flight (Q-TOF) mass spectrometer operated with an electrospray ionization (ESI) source under the following conditions: positive mode; nebulizer pressure:. Bar; flow rate of drying gas (N ): L/min; drying gas temperature: 00 C; voltage between HV capillary and HV end-plate offset: 00 V to 0 V; mass range was set from 0 to 00 m/z; and the quadrupole ion energy was.0 ev. Sodium formate was used to calibrate the system in the mass range. Results All samples were subjected to LC-MS analysis, and extracted ion chromatograms (EIC) were generated and used to characterize the constituents (Fig. ). From the plant extract, two out of of the most prominent chromatogram peaks were identified as the Veratrum alkaloids verazine and veratramine. Four alkaloids previously isolated from Veratrum species were identified from the extracted biomass of V. parviflorum: the mass spectrometry data in support of verazine (m/z.), veratramine (m/z 0.), cyclopamine (m/z.), and veratridine (m/z.) is shown in Figure. Additional EIC signals correlating to ions with the following m/z:.,.,., 0., and.0 amu, are consistent with jervine derivatives. The molecular formulas determined for these ions correlate to the following molecular formulas: C H NO, C H NO, C H NO, C H NO, and C H NO, respectively. These alkaloids eluted between and minutes in the HPLC gradient, and this region and the peaks of interest are shown in Figure. Additional prominent ions observed in the plant biomass included

3 Clinical Toxicology Page of 0 m/z = 0.,., and 00. amu. The molecular formulas predicted for these ions were C H NO, C H NO, and C H NO, respectively. The analyzed biomass had been cooked in water: the heating process did not destroy the isolated alkaloids and the alkaloids were still present in the plant material. In summary, the ions with identical m/z and retention times observed in the extracted biomass and patient samples constituted.% ( of ),.% ( of ), and.% ( of ) for Patient plasma, Patient serum, and Patient plasma, respectively.

4 Page of Clinical Toxicology 0 Figure : Total ion chromatograms for a) Patient Plasma, b) Patient Serum, c) Patient Plasma, d) AB Serum Standard, e) Spiked Serum, and f) V. parviflorum extract. xmm ( x DPI)

5 Clinical Toxicology Page of 0 Figure : EIC and corresponding MS for Veratrum alkaloids identified from the extracted biomass of V. parviflorum, including: verazine, a-b, (m/z.); veratramine, c-d, (m/z 0.); cyclopamine, e-f, (m/z.); and veratridine, g-h, (m/z.). xmm ( x DPI)

6 Page of Clinical Toxicology 0 Figure : The alkaloid region of the chromatogram of the Veratrum parviflorum extract is shown, with the m/z of peaks of interest labeled. xmm ( x DPI)

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