Heliotrine

Manufactured by Phytolab

Sourced in Germany

Heliotrine is a laboratory instrument designed for the analysis and characterization of plant-based compounds. It utilizes advanced spectroscopic techniques to provide detailed information about the chemical composition and structure of samples.

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Lab products found in correlation

Echimidine, by Phytolab (9 mentions) Lasiocarpine, by Phytolab (5 mentions) Echimidine n oxide, by Phytolab (5 mentions) Heliotrine n oxide, by Phytolab (5 mentions) Senecionine, by Phytolab (5 mentions) Senkirkine, by Phytolab (4 mentions) Lycopsamine, by Phytolab (4 mentions) Europine, by Phytolab (3 mentions) Indicine, by Phytolab (3 mentions) Intermedine, by Phytolab (3 mentions) Retrorsine, by Phytolab (3 mentions) Erucifoline n oxide, by Phytolab (3 mentions) Lycopsamine n oxide, by Phytolab (3 mentions) Seneciphylline, by Phytolab (3 mentions) Monocrotaline, by Phytolab (3 mentions) Erucifoline, by Phytolab (3 mentions) Jacobine, by Phytolab (3 mentions) Formic acid, by Merck Group (3 mentions) Caffeine, by Merck Group (3 mentions) Senecivernine, by Phytolab (2 mentions)

9 protocols using heliotrine

Comprehensive Analytical Standards for Pyrrolizidine Alkaloids

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Analytical standards of all pyrrolizidine alkaloids and their N-oxide were purchased from Phytolab (Vestenbergsgreuth, Germany): Echimidine (Em), Echimidine-N-oxide (EmNO), Echinatine (En), Echinatine-N-oxide (EnNO), Erucifoline-N-oxide (ErNO), Europine (Eu), Europine-N-oxide (EuNO), Heliosupine (Hs), Heliosupine-N-oxide (HsNO), Heliotrine (Ht), Heliotrine-N-oxide (HtNO), Indicine (Id), Indicine-N-oxide (IdNO), Integerrimine (Ir), Integerrimine-N-oxide (IrNO), Intermedine (Im), Intermedine-N-oxide (ImNO), Lasiocarpine (Lc), Lycopsamine (Ly), Lycopsamine-N-oxide (LyNO), Retrorsine (Rt), Retrorsine-N-oxide (RtNO), Rinderine (Rn), Rinderine-N-oxide (RnNO), Senecionine (Sn), Senecionine-N-oxide (SnNO), Seneciphylline (Sp), Seneciphylline-N-oxide (SpNO), Senecivernine (Sv), Senecivernine-N-oxide (SvNO), Senkirkine (Sk), Spartioidine (St), Spartioidine-N-oxide (StNO), Usaramine (Us) and Usaramine-N-oxide (UsNO). Methanol (LC-MS grade) was from VWR Chemicals (Rosny-sous-Bois-cedex, France), sulphuric acid (96%) and acetonitrile (LC-MS grade) were from Carlo Erba Reagents (Val de Reuil Cedex, France), formic acid was from Carlo Erba Reagents (Milan, Italy) and ammonium formate (analytical grade) was from Sigma-Aldrich (St. Louis, MO, USA). Ultrapure water used throughout the experiments was produced by an EvoQua Water Technologies system (Diessechem, Milan, Italy).

Roncada P., Isani G., Peloso M., Dalmonte T., Bonan S, & Caprai E. (2023). Pyrrolizidine Alkaloids from Monofloral and Multifloral Italian Honey. International Journal of Environmental Research and Public Health, 20(7), 5410.

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Pyrrolizidine Alkaloids: Preparation and Handling

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The investigated PAs (indicine, heliotrine, lycopsamine, europine, echimidine, lasiocarpine, riddelliine, retrorsine, monocrotaline, senecionine, seneciphylline) were of highest purity and obtained from Phytolab (Vestenbergsgreuth, Germany). Stock solutions of PAs were prepared in suitable solvents (50–150 mM) and stored at −20 °C. heliotrine, lycopsamine, echimidine, lasiocarpine, riddelliine, monocrotaline were dissolved in DMSO, whereas senecionine and seneciphylline were dissolved in a 1:1 mixture (v:v) of DMSO and acetonitrile. retrorsine was dissolved in ethanol. Stock solutions were diluted in cell culture medium to reach final concentrations in the cell experiments.

Haas M., Wirachowski K., Thibol L., Küpper J.H., Schrenk D, & Fahrer J. (2023). Potency ranking of pyrrolizidine alkaloids in metabolically competent human liver cancer cells and primary human hepatocytes using a genotoxicity test battery. Archives of Toxicology, 97(5), 1413-1428.

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Structural Diversity of Pyrrolizidine Alkaloids

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The structurally different PAs echimidine (94% purity), heliotrine (91% purity), lasiocarpine (98% purity), senecionine (99% purity), and senkirkine (98% purity) were purchased from PhytoLab (Verstenbergsgreuth, Germany). Platyphylline (95% purity) was purchased from BOC Sciences (New York, USA). PAs were dissolved in 0.15 M NaCl. Due to the poorer solubility, senecionine was first dissolved in 0.2 M hydrochloric acid, then the pH was adjusted to 6–7 and afterwards NaCl was added to a final concentration of 0.15 M.

Buchmueller J., Sprenger H., Ebmeyer J., Rasinger J.D., Creutzenberg O., Schaudien D., Hengstler J.G., Guenther G., Braeuning A, & Hessel-Pras S. (2021). Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Archives of Toxicology, 95(8), 2785-2796.

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PA and PANO Reference Substances

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Reference substances for 25 PA and PANO were purchased from Phytolab, Vestenbergsgreuth, Germany (echimidine, echimidine N-oxide, europine, europine N-oxide, erucifoline, erucifoline N-oxide, heliotrine, heliotrine N-oxide, intermedine, intermedine N-oxide, jacobine, jacobine N-oxide, lasiocarpine, lasiocarpine N-oxide, lycopsamine, lycopsamine N-oxide, monocrotaline, monocrotaline N-oxide, retrorsine, retrorsine N-oxide, senecionine, senecionine N-oxide, seneciphylline, seneciphylline N-oxide, and senkirkine). Stock solutions (c = 1.0 mg/mL) of each PA/PANO were prepared either with acetonitrile or acetonitrile/water (50/50, v/v), depending on the solubility, and stored at 4 °C in the dark. A PA/PANO mix solution (c = 1.0 µg/mL of each analyte) was used to prepare calibration standards and for the validation experiments. Water, acetonitrile and methanol were used in LC–MS grade (Th. Geyer, Renningen, Germany). Ammonia solution (32%) was purchased from Th. Geyer as well. Formic acid and ammonium formate used as eluent additive (LC–MS/MS grade) were from Sigma Aldrich (Deisenhofen, Germany).

Gottschalk C., Kaltner F., Zimmermann M., Korten R., Morris O., Schwaiger K, & Gareis M. (2020). Spread of Jacobaea vulgaris and Occurrence of Pyrrolizidine Alkaloids in Regionally Produced Honeys from Northern Germany: Inter- and Intra-Site Variations and Risk Assessment for Special Consumer Groups. Toxins, 12(7), 441.

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Comprehensive Pyrrolizidine Alkaloid Standard Analysis

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In total, 30 pyrrolizidine alkaloid standards were utilized in a high resolution accurate mass (HRAM) LC-MS/MS screen. Echimidine, erucifoline, europine, heliotrine, indicine, intermedine, jacobine, lasiocarpine lycopsamine, monocrotaline, retrorsine senecionine, seneciphylline, senecivernine, and their respective N-oxides, were purchased together with senkirkine and trichodesmine from Phytolab GmbH & Co. KG (Vestenbergsgreuth, Germany) and had a purity >89%. All other chemicals and solvents were of analytical reagent or HPLC grade purity. Water used for sample preparation and HPLC was Milli-Q purified (Merck Millipore, Darmstadt, Germany).

Hungerford N.L., Carter S.J., Anuj S.R., Tan B.L., Hnatko D., Martin C.L., Sharma E., Yin M., Nguyen T.T., Melksham K.J, & Fletcher M.T. (2019). Analysis of Pyrrolizidine Alkaloids in Queensland Honey: Using Low Temperature Chromatography to Resolve Stereoisomers and Identify Botanical Sources by UHPLC-MS/MS. Toxins, 11(12), 726.

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Extraction and Preparation of Pyrrolizidine Alkaloids

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Echimidine (94% purity), heliotrine (91% purity), lasiocarpine (98% purity), senecionine (99% purity) and senkirkine (98% purity) were purchased from PhytoLab (Verstenbergsgreuth, Germany). Platyphylline (95% purity) was purchased from BOC Sciences (New York, New York, USA). senecionine was dissolved in 0.2-M hydrochloric acid. Afterwards, pH was adjusted to 6–7 using 0.2-M sodium hydroxide solution. Sodium chloride (NaCl) was added to obtain a solution containing 0.15-M NaCl. All other PA were dissolved in 0.15-M aqueous NaCl solution.

Ebmeyer J., Rasinger J.D., Hengstler J.G., Schaudien D., Creutzenberg O., Lampen A., Braeuning A, & Hessel-Pras S. (2020). Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Archives of Toxicology, 94(5), 1739-1751.

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Quantification of Pyrrolizidine Alkaloids

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Analytical standards were obtained from different suppliers as follows: echimidine (purity 97%), echimidine N-oxide (purity 97%), heliotrine (purity 91%), heliotrine N-oxide (purity 91%), lycopsamine (purity 80%) and lycopsamine N-oxide (purity 80%) from PhytoLab GmbH & Co. KG (Vestenbergsgreuth, Germany); senecionine (purity 99%), senecionine N-oxide (purity 99%), seneciphylline (purity 94%) and seneciphylline N-oxide (purity 94%) from Carl Roth & Co. KG (Karlsruhe, Germany); indicine-N-oxide (purity 99%), intermedine (purity 99%), jacobine (purity 98%), jacobine N-oxide (purity 98%), retrorsine (purity 90%), retrorsine N-oxide (purity 96.0%) and senkirkine (purity 98%) from Phytoplan (Heidelberg, Germany); caffeine (purity 98%), used as an internal standard, was from Sigma-Aldrich (Steinheim, Germany).
Methanol (LC-MS grade) and sulphuric acid (98% purity, analytical grade) were from Carlo Erba reagents (Milan, Italy). Ammonia (28% purity, analytical grade) was from VWR Chemicals. Formic acid (98% purity, LC-MS grade) was from Sigma-Aldrich. Ultra-pure water was obtained from a water purification system (Purelab Classic, ELGA Lab Water, High Wycombe, UK).

Inacio L.D.J., Lanza I., Merlanti R., Contiero B., Lucatello L., Serva L., Bisutti V., Mirisola M., Tenti S., Segato S., & Capolongo F. (2020). Discriminant analysis of pyrrolizidine alkaloid contamination in bee pollen based on near-infrared data from lab-stationary and portable spectrometers. European Food Research and Technology, 246(12), 2471-2483.

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Quantification of Pyrrolizidine Alkaloids

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De Jesus Inacio L., Lanza I., Merlanti R., Contiero B., Lucatello L., Serva L., Bisutti V., Mirisola M., Tenti S., Segato S, & Capolongo F. (2021). Discriminant analysis of pyrrolizidine alkaloid contamination in bee pollen based on near-infrared data from lab-stationary and portable spectrometers. Eur Food Res Technol., 246(12).

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Quantitative Analysis of Pyrrolizidine Alkaloids

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Methanol (MeOH) (MS grade), acetonitrile (MeCN) (MS grade), formic acid (FA) (MS grade), ammonium formate (MS grade), acetone (HPLC grade), sulfuric acid, hydrochloric acid (Analytical reagent grade) and caffeine (internal standard, for spiking experiments and method validation) were purchased from Sigma-Aldrich (Steinheim, Germany). Glass fibre (SiO₂, particle size 0.2–0.8 mm) was purchased from Merck (Darmstadt, Germany). Certified reference materials of heliotrine, monocrotaline, monocrotaline N-oxide, senecionine, senecionine N-oxide, erucifoline, erucifoline-N-oxide, retrorsine, jacobine, jacobine N-oxide senkirkine, heliotrine N-oxide, echimidine, echimidine N-oxide, purchased from Phytolab (Vestenbergsgreuth, Germany), also lindelofine, lindelofine N-oxide purchased from AKos Consulting & Solutions (Steinen, Germany). Oasis MCX 6 cc, 150 mg Sorbent, 30 μm particle size purchased from Waters (Milford, USA). MilliQ water (resistivity 18.2 Mohm × cm, TOC less than 1 μg L⁻¹) was produced in-house with a type I ultrapure water purification system from ELGA-Veolia LabWater (High Wycombe, UK).

Hama J.R, & Strobel B.W. (2019). Pyrrolizidine alkaloids quantified in soil and water using UPLC-MS/MS. RSC Advances, 9(52), 30350-30357.

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