Published October 31, 2018
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Table 2 1 H, 13 C in Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance
Authors/Creators
- 1. Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia
- 2. Natural History Museum, Njegoševa 51, 11000 Belgrade, Serbia
- 3. Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA
- 4. Department of Organic Chemistry, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia
Description
Table 2 1 H, 13 C, DEPT, HMBC, and NOESY/ROESY data of compounds 1, 2 and 3 in D O.
| Pos. | 1 a | Pos. | 2 b | 3 a | |||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δ H | δ C | HMBC | NOESY | δ H | δ C | HMBC | ROESY | δ H | δ C | HMBC | ROESY | ||||
| 1 | 5.71 dd (9.8, 2.0) | 140.41 | 3, 14 | 2 | 1 | 3.04 d (4.0) | 43.95 | 2 α / β, 5, 9 β | 2.97 q (8.2) | 43.90 | 2 α, 3, 7, 9 β, 14a/b | 1, 2 β, 14b | |||
| 2 | 5.59 dd (9.6, 2.5) | 125.61 | 1 | 2 | α | 1.71 m | 36.98 | 1.84 td (14.2, 7.2) | 36.48 | 1 | 9 α | ||||
| β | 2.35 m | 6, 9 β | 2.31 td (13.2, 8.1) | 3 | |||||||||||
| 3 | 4.89 s | 78.05 | 1, 5, 15a, 1′ | 1, 5, 1′ | 3 | 4.63 t (8.2) | 72.25 | 2 α, 15a/b | 2 β, 5 | 4.62 t (6.7) | 80.93 | 1, 2 α / β, 15a/b, 1′ | 5, 15b, 1′ | ||
| 4 | – | 141.26 | 5 | 4 | – | 152.39c | 2 β, 3, 5, 15b | – | 148.81 | 3, 6, 7, 15a/b | |||||
| 5 | 2.57 d (11.1) | 50.39 | 14,15a | 3, 9 α | 5 | 3.01 d (11.6) | 49.26 | 1, 2 α | 7, 9 α, 15b | 2.30 t (9.3) | 53.20 | 1, 3, 7, 11 | |||
| 6 | 4.52 t (11.0) | 77.52 | 5 | 8, 11, 14, 15a | 6 | 4.37 t (9.6) | 80.14 | 1, 5, 7 | 2 β, 8, 9 β, 11 | 4.33 t (10.1) | 80.29 | 9 β | 15a, 5″b | ||
| 7 | 2.16 q (11.5) | 55.82 | 1, 13 β, 14 | 7 | 2.49 d (9.5) | 52.65 | 9 α / β, 13 β | 13 α | 2.89 t (9.8) | 49.67 | 1, 5, 6, 9 β, 15a/b | 5, 15b | |||
| 8 | 4.10 dd (12.1, 4.4) | 66.54 | 9 β | 6, 14 | 8 | 4.09 m | 70.93 | 6, 9 α / β | 6, 9 β, 11, 13 α | 4.01 dd (9.7, 4.0) | 70.35 | 9 β | |||
| 9 | α | 1.41 t (11.7) | 45.05 | 14 | 5, 8, 9 β, 11 | 9 | α | 2.33 dd (14.6, 7.6) | 42.87 | 14a/b | 2.21 dd (13.9, 4.9) | 42.80 | |||
| β | 2.01 dd (12.6, 4.5) | 9 α, 14 | β | 2.79 dd (13.1, 4.8) | 2 β, 6, 8 | 2.69 dd (14.0, 4.8) | 14a, 6′ β | ||||||||
| 10 | – | 39.41 | 1, 2, 5, 9 β | 10 | – | 143.08 | 1, 2 β, 5, 9 β | – | 143.25 | 1, 2 α, 9 α / β, 14b | |||||
| 11 | 3.26 d (9.3) | 42.34 | 13 β | 5, 9 | 11 | 3.34 t (7.7) | 43.03 | 13 β | 3.24 t (8.4) | 43.18 | 13 α | 7, 9 β | |||
| 12 | – | 173.88 | 13 α | 12 | – | 177.75c | 6, 11 | – | 177.61 | 11 | |||||
| 13 | α | 3.47 t (10.1) | 55.03 | 5″b | 13 β | 13 | α | 3.72 q (7.7) | 55.20 | 7, 11 | 3.23 dd (11.2, 2.3) | 55.33 | |||
| β | 3.68 t (8.9) | 13 α | β | 3.58 q (6.7) | 3.84 dd (8.4, 1.8) | ||||||||||
| 14 | 0.87 s | 20.86 | 5 | 1, 6, 8 | 14 | a | 5.10 brs | 115.34 | 9 α | 4.98 s | 116.33 | 1, 9 α / β | 9 β, 3″a | ||
| b | 5.10 brs | 5.06 s | 1, 2 α, 3 | ||||||||||||
| 15 | a | 4.95 s | 107.85 | 3, 5 | 6, 15b | 15 | a | 5.30 s | 110.59 | 5.37 s | 114.64 | 3 | 6 | ||
| b | 5.48 s | 15a, 1′ | b | 5.34 s | 5.40 s | 3, 5, 1′ | |||||||||
| 1′ | 4.58 d (7.9) | 103.25 | 2′ | 3, 15b, 3′, 5′ | 1′ | 4.53 d (7.9) | 100.99 | 3, 3′, 4′ | 1, 15b, 3′, 5′ | ||||||
| 2′ | 3.29 t (7.9) | 73.57 | 2′ | 3.34 d (9.4) | 75.87 | 1′, 3′, 4′, 6′ α | |||||||||
| 3′ | 3.43 d (1.8) | 75.98 | 2′ | 1′, 5′ | 3′ | 3.88 | 73.18 | 1′, 4′ | 1′ | ||||||
| 4′ | 3.35 d (1.8) | 69.63 | 2′, 3′, 6′ β | 4′ | 3.40 t (8.9) | 70.44 | |||||||||
| 5′ | 3.37 d (1.9) | 75.90 | 3′, 6′ β | 1′, 3′ | 5′ | 3.28 t (9.2) | 73.23 | ||||||||
| 6′ | α | 3.64 dd (12.6, 2.20) | 60.72 | 6′ | α | 3.63 t (5.2) | 60.87 | 4′ | |||||||
| β | 3.85 dd (12.4, 1.9) | β | 3.89 dd (13.6, 1.3) | 6, 9 β | |||||||||||
| 1″ | – | 177.32 | 1″ | – | 174.59c | 2″ | – | 175.21 | |||||||
| 2″ | 4.05 d (9.5) | 70.48 | 13 α | 3″b, 4″b | 2″ | 4.15 m | 70.15 | 3.36 dd (6.9, 1.8) | 69.75 | 13 β, 5″a/b | |||||
| 3″ | a | 2.16 m | 29.08 | 3″b | 3″ | a | 2.26 q (8.0) | 28.50 | 2″ | 2.20 m | 28.90 | 4″a/b | |||
| b | 2.43 m | 2″, 3″a | b | 2.45 d (9.9) | 2.47 m | 4″b | |||||||||
| 4″ | a | 1.91 m | 23.55 | 4″b | 4″ | a | 2.01 m | 23.31 | 3″a | 3″a | 1.98 m | 23.53 | |||
| b | 2.14 m | 2″, 4″a, 5″b | b | 2.22 m | 2.16 m | 3″b | |||||||||
| 5″ | a | 3.82 d (6.0) | 56.04 | 5″ | a | 3.32 m | 55.01 | 13 α | 3.49 dd (12.7, 6.5) | 55.51 | |||||
| b | 3.23 d (5.8) | b | 3.93 m | 3.64 dd (11.3, 6.2) |
a 1 H (400 MHz), 13 C (101 MHz), at 298 K. b 1 H (500 MHz), 13 C (125 MHz), at 292–295 K. c Resolved in HMBC.
Notes
Published as part of Milutinović, Violeta, Niketić, Marjan, Krunić, Aleksej, Nikolić, Dejan, Petković, Miloš, Ušjak, Ljuboš & Petrović, Silvana, 2018, Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance, pp. 22 in Phytochemistry 154 on page 22, DOI: 10.1016/j.phytochem.2018.06.008, http://zenodo.org/record/10484041
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