4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General Experimental Procedures
3.2. Plant Materials
3.3. Extraction and Isolation of the Chemical Constituents
4. Conclusions
Supplementary Materials
Acknowledgments
References
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Sample Availability: Samples of the compounds 1–3 are available from the authors. |
Position | δC, type a | δH (J in Hz) b | gHMBC c |
---|---|---|---|
1α | 53.8, CH | 2.84, ddd (9.5, 4.5, 2.5) | 14 |
2a | 24.2, CH2 | 1.41, dddd (14.5, 8.5, 6.0, 4.5) | |
2b | 1.13, m | ||
3a | 41.7, CH2 | 2.37, ddd (17.0, 8.5, 6.0) | |
3b | 2.19, ddd (17.0, 9.0, 8.5) | ||
4 | 208.8, C | 3a, 3b, 15 | |
5 | 213.4, C | 6β | |
6 α | 47.0, CH2 | 2.52, ddd (17.5, 4.5, 1.7) | |
6β | 2.13, dd (17.5, 12.0) | ||
7 | 46.4, CH | 1.84, dddd (12.0, 10.0, 4.5, 1.5) | 12, 13 |
8α | 25.1, CH2 | 1.75, m | |
8β | 1.10, m | ||
9α | 37.0, CH2 | 1.73, m | 8β, 14 |
9β | 2.04, m | ||
10 | 34.9, CH | 1.93, m | 14, 2b and/or 8β |
11 | 73.0, C | 12, 13 and/or 8β | |
12 | 26.6, CH3 | 1.13, s | 13 |
13 | 26.5, CH3 | 1.10, s | 12 |
14 | 14.0, CH3 | 0.70, d (7.5) | |
15 | 29.8, CH3 | 2.04, s |
H/C | δC, type a | δH (J in Hz) b, c | gHMBC d |
---|---|---|---|
1α | 30.9, CH2 | 2.06, dddd c (14.5, 9.8, 9.3, 6.5) | 14 |
1β | 1.51, dddd c (14.5, 8.5, 2.5, 1.5) | ||
2α | 34.6, CH2 | 2.22, ddd c (15.0, 6.5, 1.5) | |
2β | 2.19, ddd c (15.0, 9.8, 8.5) | ||
3 | 171.0, C | ||
4 | 208.0, C | 5a, 5b, 15 | |
5a, 5b | 42.2, CH2 | 2.51 br, t (7.5) | 15 |
6a | 23.8, CH2 | 1.57, ddt (14.0, 2.0, 7.5) | 8β |
6b | 1.23, ddt (14.0, 11.5, 7.0) | ||
7 | 49.2, CH | 2.26, ddt (11.5, 11.0, 2.0) | 5a, 5b, 8α, 12, 13 |
8α | 43.0, CH2 | 1.96, dd (12.5, 2.0) | |
8β | 2.53, dd (12.5, 11.0) | ||
9 | 215.4, C | 8α, 14 | |
10 | 47.7, CH | 2.71, ddq (9.3, 2.5, 7.0) | 14 |
11 | 85.0, C | 8α, 13, 12 and/or 6a | |
12 | 25.7, CH3 | 1.57, s | 13 |
13 | 20.3, CH3 | 1.26, s | 12 |
14 | 18.8, CH3 | 0.97, d (7.0) | |
15 | 30.2, CH3 | 2.10, s |
H/C | δC, type a | δH (J in Hz) b | gHMBC c |
---|---|---|---|
1 | 40.9, C | 11, 12 | |
2 | 49.4, CH2 | 2.05, d (16.0) | 11, 12 |
2 | 2.39, d (16.0) | ||
3 | 197.4, C | ||
4 | 125.5, CH | 5.77, q (2.5) | 13 |
5 | 164.0, C | 13 | |
6 | 79.1, C | 11, 12, 13, 4, 7, OH | |
7 | 129.9, CH | 5.75, d (17.0) | |
8 | 131.8, CH | 5.69, dd (17.0, 5.0) | |
9 | 71.6, CH | 4.00, m | 7 |
10 | 72.2, CH2 | 3.30–3.40, m | 1' |
11 | 23.0, CH3 | 0.93, s | 12 |
12 | 23.9, CH3 | 0.91, s | 11 |
13 | 19.0, CH3 | 1.82, d (1.5) | 4 |
1' | 66.1, CH2 | 3.30–3.40, m | |
2' | 60.2, CH2 | 3.30–3.40, m | 1' |
7-membered ring | |||||
Spatial Interaction | 71 | 72 | 73 | 74 | |
····–C1–H1…. H2a–C2–····· | 0.79 | 1.52 | 1.17 | 0.68 | |
····–C1–H1… H6α–C6–····· | 1.00 | 0.09 | ---- | 0.19 | |
····–C1–H1…. H7–C7–····· | ---- | ---- | 0.04 | 0.59 | |
····–C1–H1…. H9α–C9–····· | 0.65 | ---- | 0.67 | 0.43 | |
····–C1–H1..... H10–C10–···· | 1.81 | 1.74 | 2.07 | 0.99 | |
····–C2–H2b… CH3(14)–···· | 0.99 | ---- | 0.89 | 0.72 | |
····–C8–H8β… H6β–C6–···· | ---- | ---- | 0.63 | 0.27 | |
····–C8–H8β.... CH3(14)–···· | 1.39 | ---- | 0.78 | 0.54 | |
····–C8–H8β… O=C5–···· | ---- | 0.65 | ---- | 0.15 | |
····–C8–H8β….O-H···· | 2.10 | ---- | ---- | 0.12 | |
····–C9–H9β... .CH3(14)–···· | 0.30 | 0.76 | 0.40 | 0.75 | |
9-membered ring | |||||
91 | 92 | 93 | 94 | ||
····–C1–H1α… O=C9–····· | 1.21 | ---- | 0.02 | 0.01 | |
···–C7–H7…. O=C9–····· | 0.59 | ---- | ---- | 0.03 | |
····–C8–H8β….H10–C10–····· | 0.97 | 0.02 | ---- | 0.57 | |
····–C8–H8β….CH3(13)– ····· | 0.62 | 0.17 | 0.55 | 1.91 | |
····–CH3(12)….O=C4–····· | 11.04 | 9.24 | ---- | 8.18 | |
····–CH3(12)….O=C3–O–····· | 1.49 | 1.32 | 0.59 | 0.93 |
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Pereira, M.D.P.; Da Silva, T.; Lopes, L.M.X.; Krettli, A.U.; Madureira, L.S.; Zukerman-Schpector, J. 4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis. Molecules 2012, 17, 14046-14057. https://doi.org/10.3390/molecules171214046
Pereira MDP, Da Silva T, Lopes LMX, Krettli AU, Madureira LS, Zukerman-Schpector J. 4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis. Molecules. 2012; 17(12):14046-14057. https://doi.org/10.3390/molecules171214046
Chicago/Turabian StylePereira, Marcos D. P., Tito Da Silva, Lucia M. X. Lopes, Antoniana U. Krettli, Lucas S. Madureira, and Julio Zukerman-Schpector. 2012. "4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis" Molecules 17, no. 12: 14046-14057. https://doi.org/10.3390/molecules171214046