Introduction
Materials and methods
Chemicals and reagents
Samples and extraction
Instrumentation
Attenuated total reflectance Fourier transform infrared spectroscopy analysis
Gas chromatography–mass spectrometry analysis
Liquid chromatography coupled to tandem mass spectrometry analysis
Nuclear magnetic ressonance spectroscopy analysis
Results
ATR-FTIR analysis
GC–MS analysis
Formula | Proposed ion | Ion (m/z) | |||
---|---|---|---|---|---|
–R | |||||
–\(\hbox {CH}_2\hbox {CH}_3\) | –\(\hbox {Cl}\) | –\(\hbox {Br}\) | –\(\hbox {I}\) | ||
(25E-NBOH) | (25C-NBOH) | (25B-NBOH) | (25I-NBOH) | ||
\(\hbox {C}_{10}\hbox {H}_{14}\hbox {NO}_2\hbox {R}^{+.}\) | 180 + R | 209 | 215 | 259 | 307 |
\(\hbox {C}_9\hbox {H}_{11}\hbox {O}_2\hbox {R}^{+.}\) | 151 + R | 180 | 186 | 230 | 278 |
\(\hbox {C}_8\hbox {H}_8\hbox {O}_2\hbox {R}^{+}\) | 136 + R | 165 | 171 | 215 | 263 |
\(\hbox {C}_8\hbox {H}_8\hbox {OR}^{+}\) | 120 + R | 149 | 155 | 199 | 247 |
LC–MS/MS analysis
Formula | Proposed ion | Ion (m/z) | |||
---|---|---|---|---|---|
–R | |||||
–\(\hbox {CH}_2\hbox {CH}_3\) | –\(\hbox {Cl}\) | –\(\hbox {Br}\) | –\(\hbox {I}\) | ||
(25E-NBOH) | (25C-NBOH) | (25B-NBOH) | (25I-NBOH) | ||
\(\hbox {C}_{17}\hbox {H}_{21}\hbox {NO}_3\hbox {R}^{+}\) | 287 + R | 316 | 322 | 368 | 414 |
\(\hbox {C}_{10}\hbox {H}_{15}\hbox {NO}_{2}\hbox {R}^+\) | 181 + R | 210 | 216 | 260 | 308 |
\(\hbox {C}_{10}\hbox {H}_{12}\hbox {O}_2\hbox {R}^+\) | 164 + R | 193 | 199 | 243 | 291 |
\(\hbox {C}_9\hbox {H}_9\hbox {O}_2\hbox {R}^{+.}\) | 149 + R | 178 | 184 | 228 | 276 |
\(\hbox {C}_{10}\hbox {H}_{12}\hbox {O}_{2}^{+.}\) | 164 | 164 | 164 | 164 | 164 |
\(\hbox {C}_7\hbox {H}_7\hbox {O}^+\) | 107 | 107 | 107 | 107 | 107 |
NMR analysis
Position | \(^{1}\)H [\(\delta\) (ppm), M, J (Hz), Integral] | \(^{13}\)C [\(\delta\) (ppm)] | DEPT 135 | HMBC | |
---|---|---|---|---|---|
\(^{2}\)J | \(^{3}\)J | ||||
1 | – | 122.0 | C | – | – |
2 | – | 151.3 | C | – | – |
3 | 6.79, s, 1H | 112.1 | CH | – | C1, C12 |
4 | – | 132.6 | C | – | – |
5 | – | 151.4 | C | – | – |
6 | 6.78, s, 1H | 113.1 | CH | – | C4, C7, |
7 | 2.99, t, J = 7.5, 2H | 27.0 | \(\hbox {CH}_2\) | C1, C8 | C2, C6 |
8 | 3.21, t, J = 7.5, 2H | 47.0 | \(\hbox {CH}_2\) | C7 | C1, C9 |
9 | 4.21, s, 2H | 46.9 | \(\hbox {CH}_2\) | C1\(^\prime\) | C8, C2\(^\prime\), C6\(^\prime\) |
10 / 11 | 3.77, s, 3H; 3.88, s, 3H | 55.0; 55.1 | \(\hbox {CH}_3\) | – | C2 ; C5 |
12 | 2.60, q, J = 7.5, 2H | 23.0 | \(\hbox {CH}_2\) | C4, C13 | C3, C5 |
13 | 1.15, t, J = 7.5, 3H | 13,5 | \(\hbox {CH}_3\) | C12 | C4 |
1\(^\prime\) | – | 117.4 | C | – | – |
2\(^\prime\) | 7.31–7.26, m, 1H | 131.2 | CH | – | C9, C4\(^\prime\), C6\(^\prime\) |
3\(^\prime\) | 6.92–6.87, m, 1H | 119.3 | CH | – | C2\(^\prime\), C5\(^\prime\) |
4\(^\prime\) | 7.31–7.26, m, 1H | 131.0 | CH | – | C6\(^\prime\) |
5\(^\prime\) | 6.92–6.87, m, 1H | 115.0 | CH | – | C3\(^\prime\) |
6\(^\prime\) | – | 156.1 | C | – | – |
Position | \(^{1}\)H [ \(\delta\) (ppm), M, J (Hz), Integral ] | \(^{13}\)C [ \(\delta\) (ppm) ] | DEPT 135 | HMBC | |
---|---|---|---|---|---|
\(^{2}\)J | \(^{3}\)J | ||||
1 | – | 123.9 | C | – | – |
2 | – | 151.6 | C | – | – |
3 | 7.03–7.00, br, 1H | 113.0 | CH | C2, C4 | C1, C5 |
4 | – | 121.5 | C | – | – |
5 | – | 149.3 | C | – | – |
6 | 6.99–6.96, brs, 1H | 115.2 | CH | C5 | C2, C4, C7 |
7 | 3.02, t, J = 7.7, 2H | 26.8 | \(\hbox {CH}_2\) | C1, C8 | C2, C6 |
8 | 3.21, t, J = 7.7, 2H | 46.5 | \(\hbox {CH}_2\) | C7 | C1, C9 |
9 | 4.23, s, 2H | 46.7 | \(\hbox {CH}_2\) | C1\(^\prime\) | C8, C2\(^\prime\), C6\(^\prime\) |
10 | 3.78, s, 3H | 55.2 | \(\hbox {CH}_3\) | – | C2 |
11 | 3.83, s, 3H | 56.0 | \(\hbox {CH}_3\) | – | C5 |
1\(^\prime\) | – | 117.3 | C | – | – |
2\(^\prime\) | 7.34–7.25, m, 1H | 131.2 | CH | C9, C4\(^\prime\) | C6\(^\prime\) |
3\(^\prime\) | 6.93–6.87, m, 1H | 119.6 | CH | C2\(^\prime\), C4\(^\prime\) | C1\(^\prime\), C5\(^\prime\) |
4\(^\prime\) | 7.34–7.25, m, 1H | 131.0 | CH | – | C2\(^\prime\), C6\(^\prime\) |
5\(^\prime\) | 6.93–6.87, m, 1H | 114.9 | CH | C6\(^\prime\) | C3\(^\prime\) |
6\(^\prime\) | – | 156.1 | C | – | – |
Position | \(^{1}\)H [ \(\delta\) (ppm), M, J (Hz), Integral ] | \(^{13}\)C [ \(\delta\) (ppm)] | HMBC | |
---|---|---|---|---|
\(^{2}\)J | \(^{3}\)J | |||
1 | – | 124.8 | – | – |
2 | – | 151.9 | – | – |
3 | 7.16, s, 1H | 115.8 | C4 | C1, C5 |
4 | – | 110.0 | – | – |
5 | – | 150.0 | – | – |
6 | 6.96, s, 1H | 114.7 | – | C2, C4, C7 |
7 | 3.01, t, J = 7.6, 2H | 27.0 | C1, C8 | C2, C6 |
8 | 3.22, t, J = 7.6, 2H | 46.5 | C7 | C1, C9 |
9 | 4.23, s, 2H | 47.0 | C1\(^\prime\) | C8, C2\(^\prime\), C6\(^\prime\) |
10 | 3.79, s, 3H | 55.3 | – | C2 |
11 | 3.83, s, 3H | 55.9 | – | C5 |
1\(^\prime\) | – | 117.3 | – | – |
2\(^\prime\) | 7.33–7.25, m, 1H | 131.4 | – | C9, C4\(^\prime\), C6\(^\prime\) |
3\(^\prime\) | 6.93–6.87, m, 1H | 120.0 | – | C5\(^\prime\) |
4\(^\prime\) | 7.33–7.25, m, 1H | 131.0 | – | C2\(^\prime\), C6\(^\prime\) |
5\(^\prime\) | 6.93–6.87, m, 1H | 114.6 | – | C3\(^\prime\) |
6\(^\prime\) | – | 156.1 | – | – |