Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Materials
3.3. Extraction and Isolation
3.4. Structural Elucidation
3.5. Hepatoprotection Bioassays (In Vitro)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No | 1 a | 2 b | ||
---|---|---|---|---|
δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | |
1 | 206.2, C | 82.3, C | ||
2 | 78.8, C | 193.0, C | ||
3 | 58.2, C | 116.6, C | ||
4 | 1.98, brs | 39.3, CH | 173.0, C | |
5 | 2.45, m; 1.25, m | 36.3, CH2 | 59.7, C | |
6 | 67.1, C | 2.03, m; 1.49, m | 38.6, CH2 | |
7 | 202.5, C | 1.49, m | 42.5, CH | |
8 | 113.1, C | 46.6, C | ||
9 | 204.7, C | |||
10 | 218.7, C | 208.7, C | ||
11 | 2.90, m | 43.4, CH | 1.72, m | 48.9, CH |
12 | 1.07, d (6.4) | 20.5, CH3 | 1.08, d (6.4) | 16.7, CH3 |
13 | 1.41, d (6.4) | 23.8, CH3 | 1.27, m; 1.63, m | 27.6, CH2 |
14 | 0.88, s | 18.6, CH3 | 0.77, t (7.4) | 11.7, CH3 |
15 | 1.89, m; 1.34, m | 35.4, CH2 | 3.16, dd (14.4, 7.4) 3.02, dd (14.4, 7.4) | 22.3, CH2 |
16 | 2.10, m; 1.80, m | 27.5, CH2 | 5.06, t (7.4) | 121.3, CH |
17 | 3.04, brs | 54.7, CH | 132.6, C | |
18 | 85.4, C | 1.65, s | 25.8, CH3 | |
19 | 0.89, s | 23.8, CH3 | 1.71, s | 18.0, CH3 |
20 | 1.15, s | 26.5, CH3 | 1.77, dd (13.0, 5.6) 2.67, dd (13.0, 11.0) | 30.4, CH2 |
21 | 2.08, m; 1.70, m | 30.9, CH2 | 4.55, dd (11.0, 5.6) | 90.2, CH |
22 | 5.31, brs | 124.7, CH | 71.0, C | |
23 | 133.4, C | 1.39, s | 27.1, CH3 | |
24 | 1.62, s | 18.1, CH3 | 1.22, s | 24.2, CH3 |
25 | 1.78, s | 26.1, CH3 | 1.52, m; 2.16, m | 26.7, CH2 |
26 | 2.37, m | 44.5, CH2 | 4.94, t (7.0) | 122.4, CH |
27 | 4.00, t (6.4) | 76.1, CH | 133.6, C | |
28 | 90.1, C | 1.56, s | 18.1, CH3 | |
29 | 1.22, s | 22.9, CH3 | 1.69, s | 26.1, CH3 |
30 | 1.33, s | 28.0, CH3 | 1.05, s | 16.2, CH3 |
31 | 3.20, dd (14.4, 5.6) | 36.9, CH | 1.27, s | 22.9, CH3 |
32 | 4.87, brs | 120.4, CH | ||
33 | 136.0, C | |||
34 | 1.60, s | 18.4, CH3 | ||
35 | 1.68, s | 26.2, CH3 | ||
31-OH | 2.66, brs |
Compound | OD Value | Cell Viability (% of Control) | Inhibition (% of Control) |
---|---|---|---|
Normal | 1.717 ± 0.099 | 100.0 | |
Control | 1.001 ± 0.041 *** | 58.3 | |
GSH b | 1.328 ± 0.020 ## | 77.3 | 45.7 |
1 | 1.091 ± 0.017 # | 63.6 | 12.6 |
2 | 0.982 ± 0.030 | 57.2 | −2.7 |
3 | 1.028 ± 0.009 | 59.9 | 3.8 |
4 | 1.104 ± 0.053 | 64.3 | 14.4 |
5 | 1.033 ± 0.009 | 60.1 | 4.5 |
6 | 0.964 ± 0.010 | 56.1 | −5.2 |
7 | 0.971 ± 0.002 | 56.6 | −4.2 |
8 | 0.908 ± 0.037 # | 52.9 | −13.0 |
9 | 0.935 ± 0.015 | 54.5 | −9.2 |
10 | 0.817 ± 0.027 ## | 47.6 | −25.7 |
11 | 0.945 ± 0.016 | 55.1 | −7.8 |
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Ma, Y.; Liu, X.; Liu, B.; Li, P.; Suo, X.; Zhu, T.; Ji, T.; Li, J.; Li, X. Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum. Molecules 2022, 27, 5932. https://doi.org/10.3390/molecules27185932
Ma Y, Liu X, Liu B, Li P, Suo X, Zhu T, Ji T, Li J, Li X. Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum. Molecules. 2022; 27(18):5932. https://doi.org/10.3390/molecules27185932
Chicago/Turabian StyleMa, Yonghui, Xiaoyu Liu, Bo Liu, Pingping Li, Xinyue Suo, Tingting Zhu, Tengfei Ji, Jin Li, and Xiaoxiu Li. 2022. "Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum" Molecules 27, no. 18: 5932. https://doi.org/10.3390/molecules27185932