Pyrrolizidine Alkaloids from Onosma kaheirei Teppner (Boraginaceae)
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1 Supporting Information Rec. Nat. Prod. 10:2 (2016) Pyrrolizidine Alkaloids from nosma kaheirei Teppner (Boraginaceae) Ioanna-Maria rfanou 1, Harilaos Damianakos 1, Ioannis Bazos 2, Konstantia Graikou1 and Ioanna Chinou1* 1 Department of Pharmacy, Division of Pharmacognosy and Natural Product Chemistry, University of Athens, University Campus of Zographou, Athens, Greece 2 Department of Biology, Division of Ecology and Systematics, University of Athens, University Campus of Zographou, Athens, Greece Table of Contents Page S1: ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 3 S2: Expansion of ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N- oxide) 4 S3: HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 5 S4: Expansion of HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) S5: Expansion of HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) S6: 1 H-NMR Spectrum (400 MHz, MeH-d 4 ) of Compound 7 ((-)-3 -acetylechinatine N-oxide) S7: Expansion of 1 H-NMR Spectrum of Compound 7 ((-)-3 --acetylechinatine N- oxide) (from 0.00 to 3.40 ppm) S8: Expansion of 1 H-NMR Spectrum of Compound 7 ((-)-3 --acetylechinatine N- 10 1
2 oxide) (from 3.40 to 6.00 ppm) S9: 13 C-NMR Spectrum (50 MHz, MeH-d 4 ) of Compound 7 ((-)-3 -acetylechinatine N-oxide) S10: CSY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N- oxide) S11: Expansion of CSY Spectrum (400 MHz) of Compound 7 ((-)-3 -acetylechinatine N-oxide) (from 0.00 to 4.00 ppm) S12: Expansion of CSY Spectrum (400 MHz) of Compound 7 ((-)-3 -acetylechinatine N-oxide) (from 4.00 to 6.00 ppm) S13: HSQC-DEPT Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N-oxide) S14: HMBC Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N- oxide) S15: NESY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N- oxide) 17 2
3 S1: ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 3
4 S2: Expansion of ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 4
5 Relative Abundance KM_30013B_H20_MeH_FTMS_2_ESI(+) #2-29 RT: AV: 28 NL: 4.37E7 F: FTMS + c ESI Full ms [ ] m/z m/z Intensity Relative Delta RDB Composition Abundance (ppm) equiv C14 H C14 H12 2 N Na C15 H26 5 N C16 H22 4 Na C16 H23 4 Na C15 H26 6 N C15 H27 6 N C15 H28 6 N C15 H28 6 N C15 H25 6 N Na C15 H26 6 N Na C15 H27 6 N Na C15 H20 7 N Na C16 H35 7 N C15 H25 7 N Na C15 H25 7 N Na C16 H33 7 N Na S3: HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 5
6 Relative Abundance KM_30013B_H20_MeH_FTMS_2_ESI(+) #2-29 RT: AV: 28 NL: 4.96E4 F: FTMS + c ESI Full ms [ ] m/z m/z Intensity Relative Delta RDB equiv. Composition Abundance (ppm) C16 H16 7 N Na C17 H28 7 N S4: Expansion of HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 6
7 Relative Abundance KM_30013B_H20_MeH_FTMS_2_ESI(+) #2-29 RT: AV: 28 NL: 9.94E4 F: FTMS + c ESI Full ms [ ] m/z m/z Intensity Relative Delta (ppm) RDB Composition Abundance equiv C17 H25 7 N Na C18 H37 7 N C17 H27 7 N Na S5: Expansion of HR-ESI-MS Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) 7
8 ' 7' H 3 C H 2' 3' 5' 6' CH3 4' CH H 7 8 H N H 3 C S6: 1 H-NMR Spectrum (400 MHz, MeH-d 4 ) of Compound 7 ((-)-3 --acetylechinatine N- oxide) (-)-3 --acetylechinatine N-oxide (7): Pale yellow gum. 1 H-NMR (MeH-d 4, 400 MHz), δ: 0.91 (3H, d, H-7 ), 0.97 (3H, d, H-6 ), 1.29 (3H, d, H-4 ), 2.04 (3H, s, CCH 3 ), 2.08 (1H, m, H-6β), 2.17 (1H, sept, H-5 ), 2.60 (1H, m, H-6α), 3.68 (1H, m, H-5β), 3.83 (1H, m, H-5α), 4.33 (1H, d, H-3β), 4.63 (1H, d, H-3α), 4.67 (1H, brs, H-8), 4.73 (1H, m, H-7), 4.85 (2H, brs, H-9), 5.18 (1H, q, H-3 ), 5.92 (1H, brs, H-2). 13 C-NMR (MeH-d 4, 50 MHz), δ: 16.6 (C-4 ), 17.5 (C-6 ), 18.3 (C-7 ), 18.5 (CCH 3 ), 33.9 (C-5 ), 35.7 (C-6), 62.4 (C-9), 70.2 (C-5), 70.8 (C-7), 71.9 (C-3 ), 79.1 (C-3), 82.0 (C-2 ), 97.2 (C-8), (C-2), (C-1), (C-1 ), (CCH 3 ). ESI-MS: m/z = [M+Na] + for formula C 17 H 27 N 7 Na. 8
9 ' 7' H 3 C H 2' 3' 5' 6' CH3 4' CH 3 H-4 H-6 H H 7 8 H N H 3 C H-6β + CCH3 200 H-6α H S7: Expansion of 1 H-NMR Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) (from 0.00 to 3.40 ppm) 9
10 ' 7' H 3 C H 2' 3' 5' 6' CH3 4' CH H 7 8 H N + 5 H H 3 C H-3 H-7 H-8 H-3α H-3β H-5α H-5β S8: Expansion of 1 H-NMR Spectrum of Compound 7 ((-)-3 --acetylechinatine N-oxide) (from 3.40 to 6.00 ppm) 10
11 ' 7' H 3 C H 2' 3' 5' 6' CH3 4' CH H 7 8 H 9 1 δc 172.0, CCH3 δc 170.6, C N + - C-1 3 C-2 2 H 3 C C-8 C-3 C-3 C-7 C-5 C-9 C-6 C-5 C-7, CH3C C-6 C S9: 13 C-NMR Spectrum (50 MHz, MeH-d 4 ) of Compound 7 ((-)-3 --acetylechinatine N- oxide) 11
12 ppm (f2) S10: CSY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N-oxide) 12
13 ppm (f2) S11: Expansion of CSY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N- oxide) (from 0.00 to 4.00 ppm) 13
14 ppm (f2) S12: Expansion of CSY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N- oxide) (from 4.00 to 6.00 ppm) 14
15 Η-4 /C-4 Η-6 /C-6 Η-7 /C-7 50 Η-9/C-9 Η-7/C-7 Η-3 /C-3 Η-5α/C-5 Η-5β/C-5 Η-3α/C-3 Η-3β/C-3 Η-8/C-8 Η-2/C ppm (f2) S13: HSQC-DEPT Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N-oxide) 15
16 ppm (f2) S14: HMBC Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N-oxide) 16
17 5.0 ppm (f2) 5.0 S15: NESY Spectrum (400 MHz) of Compound 7 ((-)-3 --acetylechinatine N-oxide) 17
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