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Metformin, an Anthropogenic Contaminant of Seidlitzia

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Metformin, an Anthropogenic Contaminant of Seidlitzia Metformin, an Anthropogenic Contaminant of Seidlitzia rosmarinus Collected in a Desert Region Near the Gulf of Aqaba, Sinai Peninsula Ahmed R. Hassan,†, ║ Salah M. El-kousy,‡ Sayed A. El-Toumy,§ Karla † † ┴ *,† Frydenvang, Truong Thanh Tung, Jesper Olsen, John Nielsen, and Søren Brøgger Christensen*,† †Department of Drug Design and Pharmacology, University of Copenhagen, DK-2100 Copenhagen Ø, Denmark ‡Chemistry of Tannins Department, National Research Centre, Dokki 12622, Cairo, Egypt §Chemistry Department, Menoufia University, Shebin El-Kom 32861, EL- Menoufia, Egypt ┴ Department of Physics and Astronomy, Aarhus University, DK-8000, Aarhus C, Denmark ║Medicinal and Aromatic Plants Department, Desert Research Center, El-Matariya 11753, Cairo, Egypt Supplementary Information List of contents: Page Data for Metformin Acetate (4) S 3 Data for 2-Chloro-N-Z-feruloyltyramine (6Z) and 2-Chloro-N-E-feruloyltyramine (6E) S 6 Crystal Data, Data Collection and Refinement Data for Metformin Acetate S 9 S 1 Seidlitzia rosmarinus S 11 References S 11 S 2 Metformin Acetate: 1 1 Colorless crystals, m.p. 218.9-221.7°C (ref. 219 °C ). H NMR (600 MHz, D2O) 13 metformin moiety: δ 3.06 (6H, s, 2CH3); acetate moiety: δ 1.92 (3H, s, CH3). C NMR (150 MHz, D2O) metformin moiety: δ 37.4 (2CH3), 160.1 (C-2), 158.4 (C-4); acetate + + moiety: δ 23.3 (CH3), 181.4 (C=O). HRMS m/z 259.2102 [2M+H] (calcd for C8H23N10 259.2102). 1 Figure S1. H NMR spectrum (600 MHz, D2O) of Metformin acetate 13 Figure S2. C NMR spectrum (150 MHz, D2O) of Metformin acetate S 3 Figure S3. HSQC spectrum (D2O) of Metformin acetate Figure S4. DEPT135 spectrum (D2O) of Metformin acetate Figure S5. HMBC spectrum (D2O) of Metformin acetate S 4 Figure S6. HRMS of Metformin 1 1 Figure S7. A) H-NMR of crude extract in CD3OD; B) H-NMR of crude extract added 0.1 mg of isolated metformin. The intensity of the peak at 3.04 (singlet) is increased without creating any new signals in the spectrum. C) 1H-NMR of isolated metformin S 5 2-Chloro-N-Z-feruloyltyramine (6Z) and 2-Chloro-N-E-feruloyltyramine (6E) 1 Figure S8. H NMR spectrum (600 MHz, CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2-chloro-N-E-feruloyltyramine (6E) 13 Figure S9. C NMR spectrum (150 MHz, CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2-chloro-N-E-feruloyltyramine (6E) S 6 Figure S10. COSY spectrum (CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2- chloro-N-E-feruloyltyramine (6E) Figure S11. HSQC spectrum (CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2- chloro-N-E-feruloyltyramine (6E) Figure S12. HMBC spectrum (CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2- chloro-N-E-feruloyltyramine (6E) S 7 Figure S13. ROESY spectrum (CD3OD) of 2-chloro-N-Z-feruloyltyramine (6Z) and 2- chloro-N-E-feruloyltyramine (6E) Figure S14. HRMS of 2-chloro-N-Z-feruloyltyramine (6Z) Figure S15. HRMS of 2-chloro-N-E-feruloyltyramine (6E) S 8 X-ray Crystallographic Analysis of the Acetate of Metformin (4). Single crystals suitable for X-ray diffraction studies were grown from a solution in methanol. A single crystal was mounted and immersed in a stream of nitrogen gas [T = 123(1) K]. Data were collected, using graphite-monochromated MoK radiation ( = 0.71073 Å) on a Bruker D8 Venture diffractometer. Data collection and cell refinement were performed using the Bruker Apex2 Suite software.2 Data reduction using SAINT3 and multi-scan correction for absorption using SADABS-2012/14 were performed within the Apex2 Suite. The crystal data, data collection and the refinement data are given in Table S1. Structure Solution and Refinement. Positions of all non-hydrogen atoms were found by direct methods (SHELXS97).5 Full- matrix least-squares refinements (SHELXL97)5 were performed on F2, minimizing 2 2 2 w(Fo – kFc ) , with anisotropic displacement parameters of the non-hydrogen atoms. The position of hydrogen atoms were located in subsequent difference electron density maps. Hydrogen atoms on the methyl groups were included in calculated position with fixed isotropic displacement parameters (Uiso = 1.5Ueq). The rest of the hydrogen atoms were refined with fixed isotropic displacement parameters (Uiso = 1.2Ueq). Refinement (139 parameters, 3164 unique reflections) 2 -1 converged at RF = 0.0491, wRF = 0.1082 [2312 reflections with Fo > 4(Fo); w = 2 2 2 2 2 ( (Fo ) + (0.0529P) + 0.3475P), where P = (Fo + 2Fc )/3; S = 1.018]. The residual electron density varied between -0.33 and 0.29 e Å-3. Complex scattering factors for neutral atoms were taken from International Tables for Crystallography as incorporated in SHELXL97.5-6 Fractional atomic coordinates, a list of anisotropic displacement parameters, and a complete list of geometrical data have been deposited in the Cambridge Crystallographic Data Centre (CCDC 1525740. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures). S 9 Table S1 Crystal data, data collection and refinement data for the acetate of Metformin (4) Formula C6H15N5O2 M (g/mol) 189.23 Temperature, K 123(1) Crystal class monoclinic Space group P21/n Crystal size 0.23 x 0.17 x 0.11 mm Z 4 Cell parameters a = 9.8260(6) b = 8.8711(7) Å c = 10.6841(7) Å β = 90.834(3)° 3 V (Å ) 931.21(11) F(000) 408 dcalc (g/cm3) 1.350 θmax (°) 2.80 < θ < 33.70 Reflections measured 10196 Independent reflections 3164 Rmerge 0.0467 Number of parameters/restraints 139/0 Reflections (I > 2 σ(I)) 2312 R1/wR2 (I > 2 σ(I)) 0.0491/0.1082 R1/wR2 (all reflections) 0.0799/0.1208 2 Goodness-of-fit on F 1.018 -3 ρmax / ρmin (eÅ ) 0.29 / -0.33 S 10 Figure S16: The aerial part of Seidlitzia rosmarinus Bunge ex Boiss. Photographed and collected at the Nuweiba – Taba road, approximately 12 km from Nuweiba, Red Sea coast, South Sinai at Gulf of Aqaba in November 2012. References (1) Nishigaki, S.; Yoneda, F.; Matsumoto, H.; Morinaga, K. J. Med. Chem. 1969, 12, 39- 42. (2) Bruker Bruker AXS, Madison, Wisconsin, USA: 2011. (3) Bruker Bruker AXS Inc.: Madsion, Wisconsin, USA, 2013. (4) Bruker Bruker AXS Inc.: Madison, Wisconsin, USA, 2012. (5) Sheldrick, G. M. Acta Crystallographica, Section A: Foundations of Crystallography 2008, 64, 112-122. (6) Wilson, A. J. C. International Tables for Crystallography. Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; Vol. C. S 11 S 12 .
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