Cytotoxic Tirucallane Triterpenoids from Melia azedarach Fruits
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Compound | Yield mg/kga (w/w) |
---|---|
Melianone | 130 |
21-β-Acetoxymelianone | 16 |
Methyl kulonate | 35 |
3-α-Tigloylmelianol | 78 |
Position | 1 | 2 | |||
---|---|---|---|---|---|
δH | δC | δH | δC | ||
1a | 1.39 (m) | 32.1 | 38.5 | ||
1b | 167 (m) | ||||
2 | 1.49 (m) | 27.5 | 2.24 ddd (14.3, 14, 6.4) | 35.1 | |
1.85 (m) | 2.75 ddd (14.3, 3.6, 3.4) | ||||
3 | 4.68 (s br) | 78.3 | 216.8; 216.7 | ||
4 | 36.9 | 47.9 | |||
5 | 1.79 (m) | 46.1 | 1.82 (m) | 52.5; 52.4 | |
6 | 1.73 (m) | 22.9 | 1.70 (m) | 23.3 | |
7 | 5.23 (d, 2.4) | 118.2; 118.1 | 5.28 br | 118.2; 118.1 | |
8 | 146.0; 145.9 | 145.8; 145.6 | |||
9 | 2.30 (t, 7.6); 2.2 (t, 7.6) | 49.7; 48.8 | 49.6; 48.4 | ||
10 | 34.9 | 34.9 | |||
11 | 1.54 (m) | 17.4 | 17.8 | ||
12a | 1.53 (m) | 35.3 | 35.2 | ||
12b | 1.98 (m) | ||||
13 | 43.8; 43.6 | 43.8; 43.6 | |||
4 | 50.9; 50.4 | 50.8; 50.5 | |||
15 | 1.55 (m) | 34.2 | 34.3 | ||
16 | 1.61 (m) | 27.5; 27.1 | 27.5; 27.3 | ||
17 | 2.01 (m); 2.04 (m) | 47.1; 45.2 | 2.03 (m); 2.06 (m) | 47.1; 45.2 | |
18 | 0.90 (s) | 23.9 | 0.80 (s); 085 (s) | 24.6 | |
19 | 0.76 (s) | 13.0 | 12.8 | ||
20 | 1.71 (m) | 33.8; 31.7 | 33.8; 31.7 | ||
21 | 5.33 (d, 2.8); 5.29 (d,2.8) | 101.8; 97.8 | 101.8; 97.8 | ||
22 | 1.98 (m) | 31.5; 31.3 | 31.5; 31.3 | ||
23 | 3.89 (m); 3.83 (m) | 78.5; 77.0 | 3.88 (m); 3.84 (m) | 78.5; 77.1 | |
24 | 2.82 (d, 7.6); 2.67(d,7.6) | 67.8; 65.3 | 2.81 (d, 7.6); 2.67 (d, 7.6) | 67.8; 65.4 | |
25 | 58.0; 57.2 | 58.0; 57.2 | |||
26a) | 1.29 (s); 1.28 (s) | 25.0; 24.9 | 1.29(s); 1.28 (s) | 25.0; 24.9 | |
27a) | 1.27 (s) | 19.4; 19.2 | 1.26 (s) | 19.5; 19.2 | |
28 | 0.81 (s) | 27.6 | 0.97 (s) | 24.4 | |
29 | 0.95 (s) | 21.4 | 0.98 (s) | 21.6 | |
30 | 0.98 (s); 0.96 (s) | 22.6; 22.3 | 1.00 (s); 1.07 (s) | 22.6 | |
1′ | 167.5 | ||||
2′ | 129.2 | ||||
3′ | 6.80 (qq, 6.8, 1.6) | 136.6 | |||
4′ | 1.75 (d, 6.8) | 14.4 | |||
5′ | 1.81 (s) | 12.2 |
2.2. Cytotoxic and antiproliferative activities
2.3. Nematicidal activity
3. Experimental
3.1. General
3.2. Plant material
3.3. Extraction and isolation
3.4. Spectroscopic data
3.5. Test for in vitro cytotoxic activity
3.6. Test for in vitro antiproliferative activity
3.7. Second stage juveniles (J2) paralysis bioassays
3.8. Statistical analysis
4. Conclusions
Acknowledgements
References
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Ntalli, N.G.; Cottiglia, F.; Bueno, C.A.; Alché, L.E.; Leonti, M.; Vargiu, S.; Bifulco, E.; Menkissoglu-Spiroudi, U.; Caboni, P. Cytotoxic Tirucallane Triterpenoids from Melia azedarach Fruits. Molecules 2010, 15, 5866-5877. https://doi.org/10.3390/molecules15095866
Ntalli NG, Cottiglia F, Bueno CA, Alché LE, Leonti M, Vargiu S, Bifulco E, Menkissoglu-Spiroudi U, Caboni P. Cytotoxic Tirucallane Triterpenoids from Melia azedarach Fruits. Molecules. 2010; 15(9):5866-5877. https://doi.org/10.3390/molecules15095866
Chicago/Turabian StyleNtalli, Nikoletta G., Filippo Cottiglia, Carlos A. Bueno, Laura E. Alché, Marco Leonti, Simona Vargiu, Ersilia Bifulco, Urania Menkissoglu-Spiroudi, and Pierluigi Caboni. 2010. "Cytotoxic Tirucallane Triterpenoids from Melia azedarach Fruits" Molecules 15, no. 9: 5866-5877. https://doi.org/10.3390/molecules15095866