Four New Cyclohexylideneacetonitrile Derivatives from the Hypocotyl of Mangrove (Bruguiera gymnorrhiza)
Abstract
:1. Introduction
2. Results and Discussion
No. | δC, Mult | 1 a | 2 a | 3 a | 4 b | |||
---|---|---|---|---|---|---|---|---|
δH (J in Hz) | δC, Mult | δH (J in Hz) | δC, Mult | δH (J in Hz) | δC, Mult | δH (J in Hz) | ||
1 | 117.9, C | 117.1, C | 118.7, C | 116.8, C | ||||
2 | 97.2, CH | 5.66 (d, 1.8) | 94.7, CH | 5.53 (d, 1.5) | 94.3, CH | 5.51 (d, 1.8) | 89.4, CH | 5.6 (s) |
3 | 152.2, C | 166.0, C | 166.5, C | 170.5, C | ||||
4a | 125.4, CH | 6.20 (d, 10.0) | 29.7, CH2 | 2.46 (d, 11.9) | 29.6, CH2 | 2.45 (d, 11.0) | 25.2, CH2 | 2.79 (d, 11.0) |
4b | 2.25 (dd, 11.9, 7.8) | 2.11 (dd, 11.0, 7.8) | 2.59 (dd, 11.0, 7.8) | |||||
5a | 144.3, CH | 6.18 (dd, 10, 2.5) | 36.4, CH2 | 1.86–1.92 (m) | 36.3, CH2 | 1.69–1.74 (m) | 33.5, CH2 | 1.87–1.93 (m) |
5b | 1.19–1.24 (m) | 1.36–1.42 (m) | 1.61–1.67 (m) | |||||
6 | 62.8, CH | 4.45 (ddd, 9.0, 5.5, 2.5) | 63.9, CH | 3.92–3.87 (m) | 67.2, CH | 3.75–3.70 (m) | 67.7, CH | 4.48–4.54 (m) |
7a | 37.1, CH2 | 2.39 (ddd, 12.5, 5.5, 3.5) | 36.1, CH2 | 1.87 (ddd, 11.5, 5.2, 3.5) | 41.1, CH2 | 2.09 (ddd, 11.3, 5.0, 3.8) | 42.9, CH2 | 2.18 (ddd, 10.1, 5.0, 3.3) |
7b | 1.62 (ddd, 12.5, 10.2, 9.0) | 1.17 (ddd, 11.5, 9.7, 8.8) | 1.55 (ddd, 11.3, 9.4, 8.5) | 1.56 (ddd, 10.1, 9.3, 8.5) | ||||
8 | 73.2, CH | 4.72 (dd, 10.2, 3.5) | 73.9, CH | 3.08 (dd, 9.7, 3.5) | 74.8, CH | 3.10 (dd, 9.4, 3.8) | 65.7, CH | 4.17 (dd, 9.3, 3.3) |
1′ | 102.3, CH | 4.38 (d, 7.8) | 102.8, CH | 4.15 (d, 7.3) | 102.6, CH | 4.27 (d, 7.6) | ||
2′ | 73.8, CH | 3.16 (ddd, 8.7, 7.8, 4.5) | 75.9, CH | 2.95 (ddd, 8.5, 7.3, 4.3) | 75.8, CH | 3.09 (ddd, 8.4, 7.6, 4.3) | ||
3′ | 77.4, CH | 3.39 (ddd, 8.7, 8.7 4.2) | 77.6, CH | 3.10 (ddd, 8.7, 8.5, 4.5) | 78.8, CH | 3.11 (ddd, 8.4, 8.3, 4.5) | ||
4′ | 70.6, CH | 3.01 (ddd, 8.7, 8.7, 5.4) | 70.4, CH | 3.04 (ddd, 8.7, 8.7, 5.2) | 71.9, CH | 3.01 (ddd, 8.3, 7.8, 5.2) | ||
5′ | 77.3, CH | 3.11 (ddd, 8.7, 6.8, 6.2) | 77.5, CH | 2.94 (ddd, 8.7, 6.4, 2.4) | 78.6, CH | 3.05 (ddd, 7.8, 6.4, 2.2) | ||
6′a | 61.8, CH2 | 3.45 (ddd, 11.8, 6.2, 5.2) | 61.4, CH2 | 3.39 (ddd, 11.3, 6.2, 5.1) | 63.0, CH2 | 3.39 (ddd, 11.0, 6.2, 5.1) | ||
6′b | 3.98 (ddd, 11.8, 6.8, 2.3) | 3.65 (ddd, 11.3, 6.8, 2.2) | 3.65 (ddd, 11.0, 6.5, 2.2) | |||||
6-OMe | 49.2, CH3 | 49.2, CH3 | ||||||
6-OH | 4.79 (d, 3.5) | |||||||
2′-OH | 4.97 (d, 4.5) | 5.09 (d, 4.3) | 5.02 (d, 4.3) | |||||
3′-OH | 4.94 (d, 4.2) | 5.04 (d, 4.5) | 5.01 (d, 4.5) | |||||
4′-OH | 4.93 (d, 5.4) | 5.02 (d, 5.2) | 4.99 (d, 5.2) | |||||
6′-OH | 4.17 (d, 5.2) | 4.15 (d, 5.1) | 4.13 (d, 5.1) |
Compounds | EC50 (μg/mL) | CC50 (μg/mL) | SI (CC50/EC50) |
---|---|---|---|
1 | 23.8 ± 0.5 | 178.2 ± 13.3 | 7.5 |
2 | 30.7 ± 1.0 | 164.9 ± 10.4 | 5.4 |
3 | 19.4 ± 0.3 | 182.0 ± 6.8 | 9.4 |
4 | 8.7 ± 1.1 | 72.3 ± 4.1 | 8.3 |
5 | 5.1 ± 0.2 | 57.8 ± 3.9 | 11.3 |
6 | 7.6 ± 0.5 | 83.9 ± 2.3 | 11.0 |
7 | 80.7 ± 5.8 | 214.8 ± 14.7 | 2.7 |
Lamivudine | 0.1 ± 0.03 | / | / |
3. Experimental Section
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Acid Hydrolysis of 1–3
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Yi, X.-X.; Deng, J.-G.; Gao, C.-H.; Hou, X.-T.; Li, F.; Wang, Z.-P.; Hao, E.-W.; Xie, Y.; Du, Z.-C.; Huang, H.-X.; et al. Four New Cyclohexylideneacetonitrile Derivatives from the Hypocotyl of Mangrove (Bruguiera gymnorrhiza). Molecules 2015, 20, 14565-14575. https://doi.org/10.3390/molecules200814565
Yi X-X, Deng J-G, Gao C-H, Hou X-T, Li F, Wang Z-P, Hao E-W, Xie Y, Du Z-C, Huang H-X, et al. Four New Cyclohexylideneacetonitrile Derivatives from the Hypocotyl of Mangrove (Bruguiera gymnorrhiza). Molecules. 2015; 20(8):14565-14575. https://doi.org/10.3390/molecules200814565
Chicago/Turabian StyleYi, Xiang-Xi, Jia-Gang Deng, Cheng-Hai Gao, Xiao-Tao Hou, Fei Li, Zhi-Ping Wang, Er-Wei Hao, Yan Xie, Zheng-Cai Du, Hui-Xue Huang, and et al. 2015. "Four New Cyclohexylideneacetonitrile Derivatives from the Hypocotyl of Mangrove (Bruguiera gymnorrhiza)" Molecules 20, no. 8: 14565-14575. https://doi.org/10.3390/molecules200814565