New Lignans and Iridoid Glycosides from Dipsacus asper Wall
Abstract
:1. Introduction
2. Results and Discussion
NO. | 1 (CD3OD) | 3 (CDCl3) | 4 (CDCl3) | 5 (CDCl3) | ||||
---|---|---|---|---|---|---|---|---|
δH (J) | δC | δH (J) | δC | δH (J) | δC | δH (J) | δC | |
1 | — | 129.6 | — | 128.6 | — | 129.3 | — | 129.3 |
2 | 6.75 (s) | 103.9 | 6.92 (d, 1.8) | 109.2 | 6.97 (d, 1.8) | 112.3 | 6.93 (d, 1.8) | 109.9 |
3 | — | 149.3 | — | 147.2 | — | 146.9 | — | 147.1 |
4 | — | 136.2 | — | 145.7 | — | 145.7 | — | 145.7 |
5 | — | 149.3 | 6.76 (dd, 7.8, 1.8) | 115.2 | 6.69 (dd, 7.8, 1.8) | 114.7 | 6.77 (dd, 7.8, 1.8) | 115.1 |
6 | 6.75 (s) | 103.9 | 6.81 (d, 7.8) | 117.5 | 6.77 (d, 7.8) | 120.2 | 6.80 (d, 7.8) | 118.1 |
7 | 4,65 (s) | 87.4 | 4.53 (s) | 85.3 | 4.53 (s) | 85.4 | 4.66 (s) | 84.6 |
8 | — | 94.4 | — | 88.2 | — | 88.2 | — | 84.7 |
9α | 3.42 (d, 9.0) | 77.4 | 3.51 (d,9.0) | 74.3 | 3.54 (d, 9.0) | 74.5 | 3.39 (d,9.0) | 72.9 |
9β | 3.65 (d, 9.0) | 3.19 (d,9.0) | 3.20 (d, 9.0) | 3.68 (d,9.0) | ||||
1' | — | 133.5 | — | 127.7 | — | 128.4 | — | 128.4 |
2' | 7.07 (d, 1.8) | 111.3 | 6.97 (d, 1.8) | 112.2 | 6.93 (d, 1.8) | 102.5 | 6.64 (d, 1.8) | 103.2 |
3' | — | 149.5 | — | 146.8 | — | 147.8 | — | 147.7 |
4' | — | 148.0 | — | 145.9 | — | 134.7 | — | 134.7 |
5' | 6.77 (d, 7.8) | 116.2 | — | 115.2 | — | 147.8 | — | 147.7 |
6' | 6.85 (dd, 7.8, 1.8) | 120.8 | 6.78 (d, 1.8) | 120.2 | 6.93 (d, 1.8) | 102.5 | 6.64 d, 1.8) | 103.2 |
7' | 4.43 (d, 7.8) | 90.7 | 4.30 (s) | 88.9 | 4.30 (s) | 88.9 | 4.66 (s) | 84.5 |
8' | 2.64 (dd, 7.8, 6.6) | 64.1 | — | 85.3 | — | 85.4 | — | 84.7 |
9'α | 4.01 (dd, 9.0, 1.2) | 70.7 | 4.18 (d,9.0) | 75.5 | 4.18 (d, 9.0) | 74.5 | 3.68 (d, 9.0) | 73.0 |
9'β | 4.07 (dd, 9.0, 1.2) | 3.43 (d,9.0) | 3.44 (d, 9.0) | 3.39 (d, 9.0) | ||||
3-OMe | 3.85 (s) | 56.9 | 3.76 (s) | 55.6 | 3.76 (s) | 55.6 | 3.76 (s) | 55.5 |
5-OMe | 3.85 (s) | 56.9 | — | — | — | — | — | — |
3'-OMe | 3.87 (s) | 56.6 | 3.76 (s) | 55.6 | 3.76 (s) | 56.0 | 3.76 (s) | 55.9 |
5'-OMe | — | — | — | — | 3.76 (s) | 56.0 | 3.76 (s) | 55.9 |
NO. | 7 | 8 | ||
---|---|---|---|---|
δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | |
1a | 5.54 (d, 6.0) | 98.0 | 5.55 (d, 6.0) | 98.0 |
3a | 7.44 (s) | 153.5 | 7.44 (s) | 153.6 |
4a | — | 113.6 | — | 113.6 |
5a | 3.02 (br q, 6.0) | 30.2 | 3.01 (br q, 6.0) | 30.1 |
6a | 1.73–1.80 (m) 2.02 (ddd, 6.0, 6.0, 14.0) | 35.9 | 1.73–1.82 (m) 1.99 (ddd, 6.0, 6.0, 14.0) | 36.0 |
7a | 5.13 (dd, 4.2, 6.0) | 103.4 | 5.13 (dd, 4.2, 6.0) | 103.3 |
8a | 5.75 (ddd, 8.4, 10.2, 18.0) | 136.0 | 5.75 (ddd, 8.4, 10.2, 18.0) | 136.0 |
9a | 2.75 (ddd,5.4, 6.0, 8.4) | 45.5 | 2.75 (ddd, 5.4, 6.0, 8.4) | 45.6 |
10a | 5.29 (d, 18.0) 5.26 (d, 10.2) | 120.0 | 5.29 (d, 18.0) 5.25 (d, 10.2) | 120.0 |
11a | — | 168.6 | — | 168.6 |
12a | 3.56 (d,6.0) | 61.4 | 3.56 (d, 3.5) | 81.2 |
13a | 3.56 (d,6.0) | 79.4 | 3.56 (d, 3.5) | 79.6 |
14a | 1.19 (d,6.0) | 17.5 | 1.20 (d, 6.0) | 17.6 |
15a | 1.25 (d,6.0) | 17.6 | 1.25 (d, 6.0) | 17.7 |
1'a | 4.69 (d,7.8) | 100.4 | 4.69 (d, 7.8) | 100.4 |
2'a | 3.20 (dd,7.8,9.0) | 75.0 | 3.20 (dd, 7.8, 9.0) | 75.0 |
3'a | 3.25–3.39 (m) | 78.2 | 3.25–3.39 (m) | 78.2 |
4'a | 3.25–3.39 (m) | 71.9 | 3.25–3.39 (m) | 71.9 |
5'a | 3.25–3.39 (m) | 78.6 | 3.25–3.39 (m) | 78.6 |
6'a | 3.66 (dd, 6.0, 12.0) 3.88–3.92 (m) | 63.0 | 3.67 (dd, 6.0, 12.0) 3.91 (br d, 12.0) | 63.0 |
1b | 5.27 (d, 4.2) | 97.7 | 5.27 (d, 4.2) | 97.6 |
3b | 7.42 (s) | 152.6 | 7.42 (s) | 152.6 |
4b | — | 112.2 | — | 112.2 |
5b | 3.13 (br q, 7.8) | 32.8 | 3.12 (br q, 7.8) | 32.7 |
6b | 1.73–1.80 (m) 2.32 (br dd, 7.8, 14.4) | 40.6 | 1.74–1.82 (m) 2.32 (br dd, 7.8, 14.4) | 40.5 |
7b | 5.20 (dd, 4.2, 7.8) | 78.6 | 5.19 (dd, 4.2, 7.8) | 78.6 |
8b | 2.09–2.16 (m) | 41.2 | 2.10–2.16 (m) | 41.1 |
9b | 2.09–2.16 (m) | 47.4 | 2.10–2.16 (m) | 47.4 |
10b | 1.07 (d, 6.5) | 14.0 | 1.07 (d, 6.0) | 13.9 |
11b | — | 169.5 | — | 169.5 |
12b | 3.69 (s) | 51.9 | 3.69 (s) | 51.9 |
1'b | 4.67 (d, 7.8) | 100.3 | 4.67 (d, 7.8) | 100.3 |
2'b | 3.20 (dd, 7.8, 9.0) | 74.9 | 3.20 (dd, 7.8, 9.0) | 74.9 |
3'b | 3.25–3.39 (m) | 78.2 | 3.25–3.39 (m) | 78.2 |
4'b | 3.25–3.39 (m) | 71.8 | 3.25–3.39 (m) | 71.8 |
5'b | 3.25–3.39 (m) | 78.6 | 3.25–3.39 (m) | 78.6 |
6'b | 3.66 (dd, 6.0, 12.0) 3.88–3.92 (m) | 63.0 | 3.66 (dd,6.0,12.0) 3.89 (br d,12.0) | 63.0 |
3. Experimental Section
3.1. General
3.2. Plant Material
3.3. Extration and Isolation
3.4. Spectroscopic Data
3.5. Acid Hydrolysis of Compounds 8 and 9
3.6. HIV-1 Integrase Strand Transfer Inhibition Assays
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sun, X.; Ma, G.; Zhang, D.; Huang, W.; Ding, G.; Hu, H.; Tu, G.; Guo, B. New Lignans and Iridoid Glycosides from Dipsacus asper Wall. Molecules 2015, 20, 2165-2175. https://doi.org/10.3390/molecules20022165
Sun X, Ma G, Zhang D, Huang W, Ding G, Hu H, Tu G, Guo B. New Lignans and Iridoid Glycosides from Dipsacus asper Wall. Molecules. 2015; 20(2):2165-2175. https://doi.org/10.3390/molecules20022165
Chicago/Turabian StyleSun, Xinguang, Guoxu Ma, Dawei Zhang, Wenhua Huang, Gang Ding, Huagang Hu, Guangzhong Tu, and Baolin Guo. 2015. "New Lignans and Iridoid Glycosides from Dipsacus asper Wall" Molecules 20, no. 2: 2165-2175. https://doi.org/10.3390/molecules20022165