Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Determination of Trichilianone A (1)
2.2. Structure Determination of Trichilianone B (2)
2.3. Structure Determination of Trichilianone C (3)
2.4. Structure Determination of Trichilianone D (4)
3. Materials and Methods
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Compounds Isolated
3.5. In Vitro Leishmanicidal Activity
3.6. Cytotoxicity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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H | 1 | 2 | 3 | 4 |
---|---|---|---|---|
1 | - | 4.42 (dd, 12.3, 3.9) | 4.42 (dd, 12.1, 4.1) | - |
2a | 5.50 (s) | 3.33 (dd, 14.1, 12.3) | 3.27 (dd, 14.0, 12.1) | 5.50 (s) |
2b | - | 2.87 (dd, 14.1, 3.9) | 2.91 (dd, 14.0, 4.1) | - |
5 | 2.62 (dd, 11.7, 1.5) | 3.01 (dd, 12.9, 2.3) | 3.09 (dd, 12.6, 2.3) | 2.60 (dd, 11.6, 1.6) |
6a | 3.79 (dd, 16.8, 1.5) | 3.07 (dd, 15.0, 2.3) | 2.93 (dd, 14.2, 2.3) | 3.82 (dd, 18.6, 1.6) |
6b | 2.72 (dd, 16.8, 11.7) | 2.69 (dd, 15.0, 12.9) | 2.66 (dd, 14.2, 12.6) | 2.78 (dd, 18.6, 11.6) |
11 | 4.34 (dd, 2.6, 1.9) | 4.33 (dd, 2.3, 1.6) | 5.49 (d, 1.7) | 4.34 (dd, 2.2, 2.2) |
12 | 4.91 (d, 1.9) | 4.92 (d, 1.6) | 5.36 (d, 1.7) | 5.62 (d, 2.2) |
16a | 3.06 (dd, 18.8, 7.9) | 3.02 (dd, 18.5, 6.6) | 3.02 (dd, 18.5, 7.5) | 3.11 (dd, 18.5, 7.9) |
16b | 2.69 (dd, 12.5, 18.8) | 2.72 (dd, 18.5, 12.4) | 2.73 (dd, 18.5, 13.0) | 2.76 (dd, 18.5, 12.1) |
17 | 3.37 (dd, 12.5, 7.9) | 3.35 (dd, 12.4, 6.6) | 3.30 (dd, 13.0, 7.5) | 3.36 (dd, 12.1, 7.9) |
18 | 0.95 (s) | 0.90 (s) | 0.77 (s) | 0.97 (s) |
19 | 1.67 (s) | 1.55 (s) | 1.31 (s) | 1.69 (s) |
21 | 7.33 (dd, 1.6, 0.9) | 7.34 (dd, 1.7, 0.9) | 7.32 (dd, 1.7, 1.0) | 7.32 (dd, 1.7, 1.7) |
22 | 6.30 (dd, 1.8, 0.9) | 6.30 (dd, 1.7, 0.9) | 6.43 (dd, 1.7, 1.0) | 4.93 (t, 1.7) |
23 | 7.46 (dd, 1.6, 1.8) | 7.45 (dd, 1.7, 1.7) | 7.43 (dd, 1.7, 1.7) | - |
24 | 1.47 (s) | 1.34 (s) | 1.37 (s) | 1.46 (s) |
25 | 1.38 (s) | 1.49 (s) | 1.46 (s) | 1.40 (s) |
26 | 1.78 (s) | 1.67 (s) | 1.84 (s) | 1.78 (s) |
2′ | 2.13 (s) | 2.11 (s) | 2.07 (s) | 2.14 (s) |
MeO | 3.67 (s) | 3.68 (s) | 3.73 (s) | 3.69 (s) |
2” | - | - | 2.66 (dd, 7.1, 6.9) | - |
3” | - | - | 1.26 (d, 6.9) | - |
4” | - | - | 1.32 (d, 7.1) | - |
OH | 3.66 (d, 2.6) | not observed | - | 3.76 (d, 2.0) |
C | 1 | 2 | 3 | 4 |
---|---|---|---|---|
1 | 180.2, s | 90.8, d | 90.6, d | 180.4, s |
2 | 94.2, d | 37.3, t | 37.2, t | 94.4, d |
3 | 168.7, s | 170.9, s | 170.3, s | 168.6, s |
4 | 83.1, s | 84.9, s | 84.4, s | 83.1, s |
5 | 49.7, d | 43.2, d | 42.8, d | 49.8, d |
6 | 35.0, t | 37.7, t | 37.5, t | 35.2, t |
7 | 174.4, s | 173.8, s | 172.9, s | 174.7, s |
8 | 77.5, s | 75.5, s | 75.9, s | 77.6, s |
9 | 57.8, s | 62.8, s | 60.9, s | 58.0, s |
10 | 56.1, s | 57.2, s | 56.8, s | 56.2, s |
11 | 82.8, d | 83.6, d | 83.1, d | 82.6, d |
12 | 91.3, d | 91.2, d | 85.2, d | 91.6, d |
13 | 54.3, s | 54.2, s | 55.1, s | 53.7, s |
14 | 59.2, s | 62.8, s | 63.1, s | 58.9, s |
15 | 209.6, s | 211.8, s | 211.0, s | 208.5, s |
16 | 44.2, t | 44.8, t | 44.5, t | 43.3, t |
17 | 41.8, d | 42.2, d | 41.8, d | 42.3, d |
18 | 12.8, q | 13.1, q | 12.7, q | 13.4, q |
19 | 19.5, q | 22.6, q | 21.9, q | 19.3, q |
20 | 120.6, s | 121.2, s | 121.0, s | 132.0, s |
21 | 140.3, d | 140.2, d | 140.4, d | 173.3, s |
22 | 109.9, d | 109.9, d | 110.1, d | 148.7, d |
23 | 143.7, d | 143.7, d | 143.7, d | 70.6, t |
24 | 31.0, q | 30.9, q | 30.9, q | 31.2, q |
25 | 28.6, q | 27.0, q | 27.0, q | 28.6, q |
26 | 14.4, q | 15.2, q | 15.2, q | 14.6, q |
1′ | 172.0, s | 171.9, s | 168.5, s | 171.9, s |
2′ | 20.9, q | 20.9, q | 20.7, q | 20.8, q |
OMe | 51.9, q | 51.9, q | 52.2, q | 52.0, q |
1” | - | - | 175.0, s | - |
2” | - | - | 34.2, d | - |
3” | - | - | 18.3, q | - |
4” | - | - | 19.3, q | - |
Compound | L.a. | L.b | Raw |
---|---|---|---|
1 | >100 | >100 | 64 ± 23 |
2 | >100 | >100 | 75 ±18 |
3 | >100 | >100 | 70 ± 27 |
4 | >100 | >100 | 76 ± 23 |
Miltefosine | 5.0 ± 0.2 | 4.1 ± 0.5 | 21 ± 2.0 |
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Limachi, I.; Gonzalez-Ramirez, M.; Manner, S.; Ticona, J.C.; Salamanca, E.; Gimenez, A.; Sterner, O. Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi. Molecules 2021, 26, 1019. https://doi.org/10.3390/molecules26041019
Limachi I, Gonzalez-Ramirez M, Manner S, Ticona JC, Salamanca E, Gimenez A, Sterner O. Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi. Molecules. 2021; 26(4):1019. https://doi.org/10.3390/molecules26041019
Chicago/Turabian StyleLimachi, Ivan, Mariela Gonzalez-Ramirez, Sophie Manner, Juan C. Ticona, Efrain Salamanca, Alberto Gimenez, and Olov Sterner. 2021. "Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi" Molecules 26, no. 4: 1019. https://doi.org/10.3390/molecules26041019