Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification
Abstract
1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Procedures
3.2. Collection and Identification of Biological Materials
3.3. Extraction and Isolation
3.4. 13C-NMR and OR Calculations
3.5. Bioactive Assay of Gypmacrophin A
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Position | δH-exp a | δC-exp b | δC-cal c |
---|---|---|---|
1β | 1.41 (overlapped, 1H) | 40.9 | 40.1 |
1α | 1.13 (d, J = 14.1 Hz, 1H) | -- | -- |
2 | 1.99 (overlapped, 1H) | 49.7 | 49.8 |
3 | 2.28 (m, 1H) | 37.7 | 39.9 |
4β | 1.29 (m, 1H) | 32.4 | 33.2 |
4α | 1.94 (m, 1H) | -- | -- |
5β | 2.12 (m, 1H) | 38.8 | 40.4 |
5α | 1.53 (dd, J = 13.0, 5.7 Hz, 1H) | -- | -- |
6 | -- | 83.3 | 84.7 |
7 | -- | 24.2 | 27.4 |
8β | 0.24 (dd, J = 8.5, 4.1 Hz, 1H) | 16.4 | 16.7 |
8α | 1.02 (overlapped, 1H) | -- | -- |
9 | 0.54 (ddd, J = 11.4, 8.5, 5.5 Hz, 1H) | 24.8 | 26.3 |
10 | 1.76 (t, J = 11.4 Hz, 1H) | 38.8 | 40.2 |
11 | -- | 39.7 | 42.6 |
12β | 1.18 (dd, J = 12.7, 4.9 Hz, 1H) | 39.4 | 38.9 |
12α | 1.60 (overlapped, 1H) | -- | -- |
13 | 4.91 (dd, J = 11.7, 4.9 Hz, 1H) | 77.3 | 77.4 |
14 | -- | 49.4 | 51.9 |
15 | 1.60 (m, 1H) | 44.6 | 45.3 |
16 | 2.02 (overlapped, 1H) | 42.2 | 42.9 |
17β | 1.92 (overlapped, 1H) | 28.7 | 30.1 |
17α | 1.42 (m, 1H) | -- | -- |
18 | 4.65 (t, J = 9.0 Hz, 1H) | 81.1 | 81.9 |
19 | 0.83 (d, J = 7.4, 3H) | 15.9 | 16.2 |
20 | 1.07 (s, 3H) | 25.8 | 25.6 |
21 | 1.03 (s, 3H) | 22.8 | 22.8 |
22 | 0.92 (s, 3H) | 8.7 | 10.7 |
23 | 2.31 (m, 1H) | 28.4 | 30.6 |
24 | 0.85 (d, J = 7.3, 3H) | 23.2 | 23.2 |
25 | 0.86 (d, J = 7.3, 3H) | 15.5 | 15.4 |
AcO-13 | -- | 170.4 | 166.9 |
-- | 1.93 (s, 3H) | 21.2 | 22.1 |
AcO-18 | -- | 170.2 | 166.8 |
-- | 1.90 (s, 3H) | 20.9 | 21.8 |
HO-6 | 2.96 (s, 1H) | -- | -- |
Position | δH (2) a | δC (2) b | δH (3) a | δC (3) b | δH (4) a | δC (4) b |
---|---|---|---|---|---|---|
1 | -- | 105.1 | -- | 123.1 | -- | 121.5 |
2 | -- | 161.8 | -- | 162.3 | -- | 159.8 |
3 | -- | 109.3 | -- | 109.8 | -- | 117.1 |
4 | -- | 159.8 | -- | 161.0 | -- | 155.4 |
5 | -- | 117.3 | -- | 117.2 | -- | 125.7 |
6 | -- | 138.4 | -- | 138.6 | -- | 136. 0 |
7 | -- | 171.5 | -- | 171.0 | -- | 167.1 |
8 | 2.66 (s, 3H) | 19.5 | 2.64 (s, 3H) | 19.3 | 2.14 (s, 3H) | 17.3 |
9 | 2.23 (s, 3H) | 12.4 | 2.23 (s, 3H) | 12.6 | 2.17 (s, 3H) | 12.5 |
10 | 2.16 (s, 3H) | 8.7 | 2.16 (s, 3H) | 9.3 | 2.31 (s, 3H) | 9.8 |
1′ | 6.79 (s, 1H) | 110.8 | 6.80 (s, 1H) | 111.0 | 6.77 (s, 1H) | 110.7 |
2′ | -- | 156.8 | -- | 156.6 | -- | 156.8 |
3′ | -- | 116.6 | -- | 116.5 | -- | 122.9 |
4′ | -- | 149.2 | -- | 149.2 | -- | 149.6 |
5′ | -- | 136.1 | -- | 136.2 | -- | 127.1 |
6′ | -- | 121.0 | -- | 121.0 | -- | 133.9 |
7′ | 2.31 (s, 3H) | 20.2 | 2.31 (s, 3H) | 20.2 | 2.23 (s, 3H) | 20.3 |
8′ | 2.02 (s, 3H) | 12.6 | 2.02 (s, 3H) | 12.7 | 2.27 (s, 3H) | 12.7 |
9′ | 1.99 (s, 3H) | 9.7 | 1.99 (s, 3H) | 9.8 | 2.34 (s, 3H) | 9.9 |
CH3O-2′ | 3.85 (s, 3H) | 56.0 | 3.80 (s, 3H) | 56.1 | 3.74 (s, 3H) | 56.0 |
R2O-2 | 11.56 (s, 1H) | 11.02 (s, 1H) | 3.84 (s, 3H) | 62.1 | ||
R1O-4 | 8.18 (s, 1H) | 3.74 (s, 3H) | 60.3 | 3.81 (s, 3H) | 60.3 |
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Zhou, Y.-F.; Shi, H.-X.; Hu, K.; Tang, J.-W.; Li, X.-R.; Du, X.; Sun, H.-D.; Wang, L.-S.; Pu, J.-X. Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification. Molecules 2017, 22, 1675. https://doi.org/10.3390/molecules22101675
Zhou Y-F, Shi H-X, Hu K, Tang J-W, Li X-R, Du X, Sun H-D, Wang L-S, Pu J-X. Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification. Molecules. 2017; 22(10):1675. https://doi.org/10.3390/molecules22101675
Chicago/Turabian StyleZhou, Yuan-Fei, Hai-Xia Shi, Kun Hu, Jian-Wei Tang, Xing-Ren Li, Xue Du, Han-Dong Sun, Li-Song Wang, and Jian-Xin Pu. 2017. "Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification" Molecules 22, no. 10: 1675. https://doi.org/10.3390/molecules22101675
APA StyleZhou, Y.-F., Shi, H.-X., Hu, K., Tang, J.-W., Li, X.-R., Du, X., Sun, H.-D., Wang, L.-S., & Pu, J.-X. (2017). Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification. Molecules, 22(10), 1675. https://doi.org/10.3390/molecules22101675