Insect Antifeedant Components of Senecio fistulosus var. fistulosus—Hualtata
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General
3.2. Extraction and Isolation
3.2.1. α-Angeloyloxy-6β-acetoxy-10β-hydroxy-9-oxo-furanoeremophilane (1)
3.2.2. α-hydroxy-3α-angeloyloxy-10αH-9-oxo-furanoeremophilane (2)
3.2.3. β,10β-epoxy-6β-acetoxy-8α-hydroxy-eremophil-7(11)-en-8β,12-olide (3)
3.2.4. (+)-1(14)-en-maaliol (4)
3.2.5. 9-O-angelylpetasinecine (hectorine) (5)
3.2.6. Rosmarinine (6)
3.2.7. Crystal Structure Analysis
3.3. Insect Bioassays
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Position | 1 | 2 | ||
---|---|---|---|---|
δH in ppm, Multiplicity, J (in Hz) | δC in ppm | δH in ppm, Multiplicity, J (in Hz) | δC in ppm | |
1β | 4.84 br s | 74.5 d | 4.25 ddd (4.8, 9.7, 11.7) | 65.5 d |
2α | 2.30 m | 20.7 t | 1.50 q (11.8) | 39.1 t |
2β | 1.64 m | 2.47 m | ||
3α | 1.40 m | 23.9 t | - | 71.4 d |
3β | 2.32 m | 4.90 dt (4.6, 11.5) | ||
4α | 1.65 m | 32.3 d | 1.84 m | 46.9 d |
5 | - | 50.2 s | - | 43.9 s |
6α | 7.03 s | 68.6 d | 2.52 d (16.6) | 35.9 t |
6β | - | 2.71 d (16.6) | ||
7 | - | 139.4 s | - | 138.1 s |
8 | - | 145.9 s | - | 146.5 s |
9 | - | 186.9 s | - | 188.7 s |
10β | - | 79.8 s | 2.42 d (9.8) | 60.6 d |
11 | - | 121.8 s | - | 121.7 s |
12 | 7.41 br s | 146.9 d | 7.41 s | 145.8 d |
13 | 1.91 d (1.1) | 8.3 q | 1.99 d (1.0) | 7.8 q |
14 | 0.98 s | 15.5 q | 0.88 s | 14.3 q |
15 | 1.17 d (7.5) | 16.0 q | 0.98 d (6.7) | 10.5 q |
1’ | - | 165.7 s | - | 167.6 s |
2’ | - | 126.6 s | - | 128.1 s |
3’ | 5.92 qq (1.5, 7.2) | 140.5 d | 6.05 qq (1.4, 7.2) | 137.8 d |
4’ | 1.88 dq (1.6, 7.4) | 15.8 q | 1.97 dq (1.5, 7.2) | 15.8 q |
5’ | 1.55 quint. (1.5) | 19.9 q | 1.88 quint. (1.5) | 20.6 q |
OCOCH3 | 2.19 s | 20.9 q | - | - |
OCOCH3 | - | 170.9 s | - | - |
OH-10 | 3.98 br s | - | - | - |
Position | 3 | 7 * | ||
---|---|---|---|---|
δH in ppm, Multiplicity, J (in Hz) | δC in ppm | δH in ppm, Multiplicity, J (in Hz) | δC in ppm | |
1β | 3.18 d (4.6) | 62.7 d | 3.14 d (4.3) | 63.0 d |
2α | 1.96 dd (6.8, 10.8) | 20.3 t | 2.04 m | 21.0 t |
2β | 2.04 dd (5.9, 10.5) | 2.21 m | ||
3α | 1.36 dc (3.5, 9.4) | 23.9 t | 1.38 m | 24.2 t |
3β | 1.63 m | 1.61 m | ||
4α | 1.62 m | 32.5 d | 1.62 m | 33.0 d |
5 | - | 43.4 s | - | 43.5 s |
6α | 5.92 c (1.8) | 73.8 d | 5.69 t (1.7) | 74.3 d |
7 | - | 155.0 s | - | 153.9 s |
8 | - | 101.3 s | - | 104.4 s |
9α | 1.79 d (13.6) | 43.4 t | 1.80 d (13.6) | 43.6 t |
9β | 2.31 d (13.6) | 2.27 d (13.6) | ||
10 | - | 60.9 s | - | 61.0 s |
11 | - | 124.6 s | - | 126.8 s |
12 | - | 170.8 s | - | 170.9 s |
13 | 1.87 d (1.8) | 8.2 q | 1.92 d (1.2) | 8.6 q |
14 | 1.09 s | 14.5 q | 1.09 s | 14.5 q |
15 | 1.04 d (7.2) | 16.1 q | 1.03 d (7.0) | 16.5 q |
OMe-8 | - | - | 3.23 s | 50.9 q |
OCOCH3 | 2.20 s | 20.9 q | 2.21 s | 21.0 q |
OCOCH3 | - | 170.6 s | - | 170.3 s |
Position | δH in ppm, Multiplicity, J (in Hz) | δC in ppm | HMBC |
---|---|---|---|
1 | - | 153.6 s | - |
2a | 2.42 ddd (1.3, 6.3, 13.3) | 39.1 t | C-1, C-4, C-10, C-14 |
2b | 2.05 m | ||
3a | 1.77 m | 41.9 t | C-2, C-4 |
3b | 1.56 d | ||
4 | - | 81.1 s | - |
5α | 1.32 m | 54.6 d | C-1, C-4, C-6, C-10, C-11 |
6β | 0.47 dd (9.6, 11.4) | 30.1 d | C-4, C-8, C-11, C-13 |
7β | 0.71 ddd (6.1, 9.5, 11.4) | 27.7 d | C-5, C-11, C-13 |
8a | 1.98 m | 24.9 t | - |
8b | 1.01 m | ||
9a | 1.90 m | 26.9 t | C-5, C-10 |
9b | 1.63 m | ||
10β | 2.20 m | 53.6 d | C-1, C-2, C-5, C-6, C-14 |
11 | - | 20.4 s | - |
12 | 1.06 s | 28.8 q | C-7, C-6, C-11, C-13 |
13 | 1.04 s | 16.5 q | C-7, C-6, C-11, C-12 |
14a | 4.69 t (1.6) | 106.4 t | C-2, C-10 |
14b | 4.63 q (1.7) | ||
15 | 1.28 s | 26.2 q | C-3, C-4, C-5 |
Compound | S. littoralis | EC50 (μg/cm2) b | M. persicae | EC50 (μg/cm2) b |
---|---|---|---|---|
%FI (50 μg/cm2) a | %SI b (50 μg/cm2) a | |||
1 | 65 ± 6 * | 52 ± 7 | ||
2 | 83 ± 6 * | 0.64 (0.36-1.16) | 52 ± 7 | |
4 | 64 ± 7 * | 90 ± 3 * | 0.97 (0.71–1.32) |
Compound | Substituent | S. littoralis | M. persicae | |||
---|---|---|---|---|---|---|
C-1 | C-3 | C-6 | C-10 | %FI c (EC50) d | %SI c (EC50) d | |
1 | α-OAng | H2 | β-OAc | β-OH | 65.0 | 52.0 |
2 | α-OH | α-OAng | H2 | α-H | 83.0 (0.64) | 52.0 |
8 a | Δ1 | H2 | β-OAng | Δ10 | 32.0 | 67.0 |
9 a | Δ1 | H2 | β-OH | Δ10 | 62.0 | 71.0 |
10 a | Δ1 | H2 | β-OCOCH2CH3 | Δ10 | 45.0 | 75.0 |
11 b | H2 | H2 | β-OAc | α-H | 51.0 | 74.0 (21.9) |
12 b | H2 | H2 | β-OTigl | α-H | 65.0 | 74.0 (12.2) |
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Ruiz-Vásquez, L.; Reina, M.; Fajardo, V.; López, M.; González-Coloma, A. Insect Antifeedant Components of Senecio fistulosus var. fistulosus—Hualtata. Plants 2019, 8, 176. https://doi.org/10.3390/plants8060176
Ruiz-Vásquez L, Reina M, Fajardo V, López M, González-Coloma A. Insect Antifeedant Components of Senecio fistulosus var. fistulosus—Hualtata. Plants. 2019; 8(6):176. https://doi.org/10.3390/plants8060176
Chicago/Turabian StyleRuiz-Vásquez, Liliana, Matías Reina, Víctor Fajardo, Matías López, and Azucena González-Coloma. 2019. "Insect Antifeedant Components of Senecio fistulosus var. fistulosus—Hualtata" Plants 8, no. 6: 176. https://doi.org/10.3390/plants8060176