A New Languidulane Diterpenoid from Salvia mexicana var. mexicana
Abstract
:1. Introduction
2. Results and Discussion
H | 1 (δ ppm) b | 1 (δ ppm) c | 1 NOESY | 2 (δ ppm) c | 2 NOESY |
1 | 4.18 (1H) | 3.97 (1H) | H-2α, H-11α, | 3.33 (1H) | 2α, H-19 pro-S |
dd, J = 9.3, 1.8 | dd, J = 9.9, 2.7 | H-11β | dd, J = 12.3, 5.7 | ||
2αeq | 2.97 (1H) | 2.93 (1H) | H-1, H-2β, H-3 | 2.71 (1H) | H-1α, H-2β, |
ddd J = 21.0, 9.6, 4.2 | ddd, J = 21.0, 9.9, 4.8 | dt, J = 20.7, 5.7 | H-3 | ||
2βax | 3.28 (1H) | 3.42 (1H) | H-2α, H-3 | 2.38 (1H) | H-2α, H-3 |
ddd, J = 21.0, 3.6, 2.1 | dt, J = 21.0, 3.0 | ddd, J = 20.7, 12.3, 3.0 | |||
3 | 6.93 (1H) dd, J = 4.2, | 7.09 (1H) | H-2α, H-2β | 7.18 (1H) | H-2α, H-2β |
3.6 | t, J = 3.6 | dd, J = 5.7, 3.0 | |||
6αeq | 1.97 (1H) | 2.08 (1H) | H-6β, H-7, | 1.86 (1H) | H-6β, H-7 |
m | dd, J = 15.6, 3.0 | H-19 pro-R | dd, J = 15.6, 2.4 | ||
6βax | 1.06 (1H) | 1.10 (1H) | H-6α, H-7, H-8 | 1.79 (1H) | H-6α, H-7, H-8 |
ddd,J = 15.6, 3.6, 2.1 | dt, J = 15.6, 3.0, 2.1 | ddd, J = 15. 6, 4.5, 1.5 | |||
7 | 4.83 (1H) | 4.9 (1H) | H-6α, H-6β, | 5.12 (1H) | H-6α, H-6β, |
q, J = 3.9 | dt, J = 6.5, 3.3 | H-8, Me-17 | td, J = 4.2, 2.4 | H-8, Me-17 | |
8 | 1.97 (1H)m | 1.95 (1H)qd, J = 7.0, 4.2 | H-6β, H-7, Me-17 | 1.96 (1H)qd, J = 7.2, 4.2 | H-6β, H-7,Me-17 |
11α | 2.48 (1H) | 2.62 (1H) | H-1α, H-11β, | 2.48 (1H) | H-11β, Me-17, |
d, J = 17.1 | d, J = 17.7 | Me-17, Me-20 | d, J = 15.6 | Me-20 | |
11β | 3.43 (1H) | 3.3 (1H) | H-1α, H-11α, | 3.52 (1H) | H-11α |
d, J = 17.1 | d, J = 17.7 | d, J = 15.6 | |||
14 | 6.63 (1H) | 6.72 (1H) | H-15 | 6.71 (1H) | H-15 |
d, J = 1.4 | d, J = 1.8 | d, J = 2.0 | |||
15 | 7.57 (1H) | 7.35 (1H) | H-14 | 7.29 (1H) | H-14 |
d, J = 1.4 | d, J = 1.8 | d, J = 2.0 | |||
17 | 0.81 (1H) | 0.83 (3H) | H-7, H-8, | 0.95 (3H) | H-7, H-8, |
d, J = 6.9 | d, J = 7.0 | H-11α, Μe-20 | d, J = 7.2 | H-11α, Μe-20 | |
19 pro-R | 4.93 (1H) | 5.0 (1H) | H-6α, H-19 pro-S, | 4.7 (1H) | H-19 pro-S, |
d, J = 8.1 | d, J = 8.7 | Me-20 | d, J = 8.4 | Me-20 | |
19 pro-S | 4.50 (1H) | 4.47, (1H) | H-19 pro-R, | 4.52, (1H) | H-1, H-19 pro-R |
dd, J = 8.1, 2.1 | dd, J = 8.7, 2.1 | Me-20 | dd, J = 8.4, 1.5 | ||
20 | 1.15 (3H) | 1.15 (3H) | H-11α, Me-17, H-19 | 1.23 (3H) | H-11α, Me-17, |
s | s | pro-S and pro-R | s | H-19 pro-R | |
CH3COO | 2.10 (3H) | 2.10 (3H) | |||
s | s | ||||
-OH | 2.2 | 3.38 |
C | 1 (δ ppm) | 2 (δ ppm) |
1 | 42.7 d | 39.4 d |
2 | 23.6 t | 22.4 t |
3 | 133. 6d | 136.1 d |
4 | 130.8 s | 132.5 s |
5 | 46.1 s | 48.6 s |
6 | 34.7 t | 29.4 t |
7 | 70.9 d | 72.0 d |
8 | 37.2 d | 37.3 d |
9 | 45.3 s | 46.4 s |
10 | 77.6 s | 77.8 s |
11 | 52.0 t | 52.2 t |
12 | 194.6 s | 194.2 s |
13 | 125.7 s | 122.1 s |
14 | 109.1 d | 110.1 d |
15 | 142.4 d | 142.4 d |
16 | 159.8 s | 154.6 s |
17 | 13.0 q | 11.6 q |
18 | 169.7 s | 175.7 s |
19 | 72.5 t | 73.2 t |
20 | 20.0 q | 21.4 q |
CH3COO | 21.2 t | 21.2 q |
CH3COO | 169.0 s | 169.9 s |
3. Experimental
3.1. General
3.1. Extraction and Isolation
4. Conclusions
Supplementary Materials
Supplementary Materials
Supplementary File 1Acknowledgments
Conflict of Interest
References and Notes
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Frontana-Uribe, B.A.; Escárcega-Bobadilla, M.V.; Estrada-Reyes, R.; Morales-Serna, J.A.; Salmón, M.; Cárdenas, J. A New Languidulane Diterpenoid from Salvia mexicana var. mexicana. Molecules 2011, 16, 8866-8873. https://doi.org/10.3390/molecules16108866
Frontana-Uribe BA, Escárcega-Bobadilla MV, Estrada-Reyes R, Morales-Serna JA, Salmón M, Cárdenas J. A New Languidulane Diterpenoid from Salvia mexicana var. mexicana. Molecules. 2011; 16(10):8866-8873. https://doi.org/10.3390/molecules16108866
Chicago/Turabian StyleFrontana-Uribe, Bernardo Antonio, Martha Verónica Escárcega-Bobadilla, Rosa Estrada-Reyes, José Antonio Morales-Serna, Manuel Salmón, and Jorge Cárdenas. 2011. "A New Languidulane Diterpenoid from Salvia mexicana var. mexicana" Molecules 16, no. 10: 8866-8873. https://doi.org/10.3390/molecules16108866
APA StyleFrontana-Uribe, B. A., Escárcega-Bobadilla, M. V., Estrada-Reyes, R., Morales-Serna, J. A., Salmón, M., & Cárdenas, J. (2011). A New Languidulane Diterpenoid from Salvia mexicana var. mexicana. Molecules, 16(10), 8866-8873. https://doi.org/10.3390/molecules16108866