Fraction name
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Compound Identified
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FTIR peaks obtained
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NMR peaks obtained
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2A
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Vasicoline
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1700-1650 – C=N
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1H NMR: δ 2.15 (1H, ddt, J = 13.4, 8.0, 6.7 Hz), 2.37 (1H, dddd, J = 13.4, 7.5, 6.8, 1.7 Hz), 2.75 (6H, s), 3.42-3.61 (2H, 3.50 (ddd, J = 14.4, 6.7, 1.7 Hz), 3.53 (ddd, J = 14.4, 8.0, 6.8 Hz)), 4.18 (1H, dd, J = 7.5, 6.8 Hz), 4.61-4.83 (2H, 4.68 (d, J = 14.2 Hz), 4.76 (d, J = 14.2 Hz)), 6.52-6.70 (2H, 6.59 (ddd, J = 7.9, 7.6, 1.2 Hz), 6.64 (ddd, J = 8.1, 1.2, 0.5 Hz)), 6.78-6.93 (2H, 6.84 (ddd, J = 7.9, 1.3, 0.5 Hz), 6.86 (ddd, J = 7.9, 7.5, 1.3 Hz)), 6.95-7.19 (2H, 7.03 (ddd, J = 8.1, 7.6, 1.3 Hz), 7.13 (ddd, J = 8.1, 1.3, 0.5 Hz)), 7.20-7.34 (2H, 7.27 (ddd, J = 8.1, 7.5, 1.3 Hz), 7.28 (ddd, J = 7.9, 1.3, 0.5 Hz)).
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2B
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Vasicolinone
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1750 – C=O, 1700-1650 – C=N
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1H NMR: δ 2.16-2.45 (2H, 2.24 (dtd, J = 13.5, 8.1, 6.5 Hz), 2.37 (dtd, J = 13.5, 6.7, 1.6 Hz)), 2.75 (6H, s), 3.78-3.97 (2H, 3.86 (ddd, J = 16.3, 6.5, 1.6 Hz), 3.88 (ddd, J = 16.3, 8.1, 6.7 Hz)), 4.30 (1H, dd, J = 8.0, 6.8 Hz), 6.52-6.70 (2H, 6.59 (ddd, J = 7.9, 7.6, 1.2 Hz), 6.64 (ddd, J = 8.1, 1.2, 0.5 Hz)), 6.84 (1H, ddd, J = 7.9, 1.3, 0.5 Hz), 7.03 (1H, ddd, J = 8.1, 7.6, 1.3 Hz), 7.22-7.53 (3H, 7.29 (ddd, J = 8.0, 7.4, 1.5 Hz), 7.39 (ddd, J = 7.8, 7.4, 1.4 Hz), 7.47 (ddd, J = 7.8, 1.5, 0.5 Hz)), 8.12 (1H, ddd, J = 8.0, 1.4, 0.5 Hz).
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3A
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Adhatodine
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1700-1650 – C=N, 1200-1000 – C-N, 3050 -OH, 1755-1700 – C=O
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1H NMR: δ 2.05-2.36 (2H, 2.14 (ddt, J = 13.2, 8.0, 6.7 Hz), 2.28 (dddd, J = 13.2, 7.5, 6.8, 1.7 Hz)), 2.56 (3H, s), 3.42-3.61 (2H, 3.50 (ddd, J = 14.5, 6.7, 1.7 Hz), 3.52 (ddd, J = 14.5, 8.0, 6.8 Hz)), 3.81 (3H, s), 4.12 (1H, dd, J = 7.5, 6.8 Hz), 4.61-4.82 (2H, 4.68 (d, J = 14.2 Hz), 4.75 (d, J = 14.2 Hz)), 6.65 (1H, dd, J = 7.9, 2.6 Hz), 6.79-6.95 (2H, 6.86 (ddd, J = 7.9, 7.5, 1.3 Hz), 6.89 (dd, J = 7.9, 0.5 Hz)), 7.13 (1H, ddd, J = 8.1, 1.3, 0.5 Hz), 7.20-7.34 (2H, 7.27 (ddd, J = 8.1, 7.5, 1.3 Hz), 7.28 (ddd, J = 7.9, 1.3, 0.5 Hz)), 7.45 (1H, dd, J = 2.6, 0.5 Hz).
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3B
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Adhavasine
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1700-1650 – C=N, 3500-3150 – OH (intramolecular), 1259- Ar-O-CH3
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1H NMR: δ 2.10-2.36 (2H, 2.17 (dddd, J = 11.7, 6.8, 2.2, 1.7 Hz), 2.27 (dddd, J = 11.7, 7.9, 7.4, 6.8 Hz)), 2.57 (1H, ddd, J = 13.6, 6.8, 1.7 Hz), 2.81 (1H, ddd, J = 13.6, 7.9, 6.8 Hz), 3.81 (3H, s), 4.51-4.72 (2H, 4.58 (d, J = 13.2 Hz), 4.65 (d, J = 13.2 Hz)), 5.82 (1H, dd, J = 7.4, 2.2 Hz), 6.46-6.60 (2H, 6.52 (dd, J = 7.6, 1.5 Hz), 6.54 (dd, J = 7.9, 1.5 Hz)), 7.34 (1H, dd, J = 7.9, 7.6 Hz).
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5A
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Aniflorine
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1754 – C=O, 1700-1650 – C=N, 3500-3150 – OH (intramolecular), 1259- Ar-O-CH3
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1H NMR: δ 2.02 (1H, ddd, J = 13.9, 6.7, 1.6 Hz), 2.24 (1H, ddd, J = 13.9, 8.1, 6.5 Hz), 2.81 (6H, s), 3.73-4.00 (5H, 3.81 (ddd, J = 15.7, 6.5, 1.6 Hz), 3.91 (ddd, J = 15.7, 8.1, 6.7 Hz), 3.88 (s)), 6.61-6.82 (2H, 6.67 (ddd, J = 8.1, 1.2, 0.5 Hz), 6.75 (ddd, J = 7.8, 7.6, 1.2 Hz)), 6.88-7.10 (3H, 6.94 (dd, J = 8.5, 1.4 Hz), 7.01 (dd, J = 8.5, 7.8 Hz), 7.03 (ddd, J = 8.1, 7.6, 1.4 Hz)), 7.22 (1H, dd, J = 7.8, 1.4 Hz), 7.35 (1H, ddd, J = 7.8, 1.4, 0.5 Hz).
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5B
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Vasicinone
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1700-1650 – C=N, 3500-3150 – OH, ), 1754 – C=O
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1H NMR: δ 2.15 (1H, dtd, J = 12.1, 8.1, 6.5 Hz), 2.33 (1H, dtd, J = 12.1, 6.7, 1.6 Hz), 3.71-3.89 (2H, 3.79 (ddd, J = 15.8, 6.5, 1.6 Hz), 3.81 (ddd, J = 15.8, 8.1, 6.7 Hz)), 5.27 (1H, dd, J = 8.0, 6.8 Hz), 7.22-7.54 (3H, 7.29 (ddd, J = 8.0, 7.4, 1.5 Hz), 7.39 (ddd, J = 7.8, 7.4, 1.4 Hz), 7.47 (ddd, J = 7.8, 1.5, 0.5 Hz)), 8.12 (1H, ddd, J = 8.0, 1.4, 0.5 Hz).
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BA
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Vasicine
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3300-3000 – NH, 2000-1650 – CH (aromatic ring), 1700-1650 – C=N, 3500-3150 – OH
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1H NMR: δ 2.02-2.19 (2H, 2.11 (ddt, J = 14.0, 7.4, 6.8 Hz), 2.11 (dddd, J = 14.0, 7.5, 2.2, 1.7 Hz)), 3.26-3.55 (2H, 3.34 (ddd, J = 14.0, 7.4, 2.2 Hz), 3.47 (ddd, J = 14.0, 7.5, 6.7 Hz)), 4.68-4.85 (2H, 4.75 (d, J = 14.0 Hz), 4.78 (d, J = 14.0 Hz)), 4.98 (1H, dd, J = 6.8, 1.7 Hz), 6.87 (1H, ddd, J = 7.9, 7.5, 1.3 Hz), 7.07-7.31 (3H, 7.13 (ddd, J = 8.2, 1.3, 0.6 Hz), 7.24 (ddd, J = 8.2, 7.5, 1.3 Hz), 7.24 (ddd, J = 7.9, 1.3, 0.6 Hz)).
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