Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis littoralis
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation
2.2. Anti-SARS-CoV-2 Activity and Cytotoxicity
3. Materials and Methods
3.1. General Experimental Procedure
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Computational Details
3.5. Anti-SARS-CoV-2 Assay
3.5.1. Cells and Virus
3.5.2. Antiviral Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Experimental | Calculated | |||
---|---|---|---|---|
Position | δC, Type | δH (J in Hz) | δC | δH |
1 | 24.4, CH2 | 1.67 m | 25.1 | 1.53 |
1 | 24.4, CH2 | 1.85 * | 25.1 | 2.11 |
2 | 26.9, CH2 | 1.81 * | 26.9 | 2.23 |
2 | 26.9, CH2 | 1.45 m | 26.9 | 1.15 |
3 | 64.7, CH | 4.09 m | 64.2 | 3.91 |
4 | 31.2, CH2 | 2.00 * | 29.2 | 2.08 |
4 | 31.2, CH2 | 2.32 m | 29.2 | 2.33 |
4a | 88.9, CH | 4.31 t (3.2) | 90.2 | 4.50 |
6 | 52.7, CH2 | 3.83 d (15.0) | 50.3 | 3.71 |
6 | 52.7, CH2 | 3.97 d (15.0) | 50.3 | 3.95 |
6a | 128.9, C | - | 135.1 | - |
7 | 120.6, CH | 6.51 d (8.0) | 120.0 | 6.52 |
8 | 114.9, CH | 6.55 d (8.0) | 112.2 | 6.57 |
9 | 141.1, C | - | 140.5 | - |
10 | 146.0, C | - | 144.5 | - |
10a | 135.5, C | - | 134.5 | - |
10b | 47.2, C | - | 49.2 | - |
11 | 36.5, CH2 | 1.75 * | 39.7 | 1.71 |
11 | 36.5, CH2 | 1.98 * | 39.7 | 1.83 |
12 | 46.5, CH2 | 3.26 m | 44.4 | 3.20 |
12 | 46.5, CH2 | 3.19 m | 44.4 | 3.19 |
CMAE | 1.8 | 0.13 | ||
Max. outlier | 6.2 | 0.42 |
Compound 1 | Compounds 2 and 3 | |||
---|---|---|---|---|
Diastereomer | Probability (%) | Diastereomer | Probability (%) | JH-4a/H-10b |
SRR | 26.78 | SRRR | 0 | 10.69 |
SRS | 0 | SRRS | 61.05 | 5.52 |
SSR | 73.22 | SRSR | 0 | 7.36 |
SSS | 0 | SRSS | 0 | 10.56 |
SSRR | 0 | 10.25 | ||
SSRS | 10.15 | 5.78 | ||
SSSR | 0 | 7.99 | ||
SSSS | 28.80 | 10.85 |
Compound 1 | Compounds 2 and 3 | |||
---|---|---|---|---|
Experimental | −63.6 | −8.0 | ||
B3LYP/6-31++G(d,p)// 6-311++G(3df,2dp) | SSR RRS | −48.8 48.7 | SRSS RSRR | −230.4 230.6 |
B3LYP/6-31++G(d,p)// aug-cc-pVTZ | SSR RRS | −46.8 46.6 | SRSS RSRR | −227.7 227.9 |
In CD3OD | In (CD3)2SO | |||||
---|---|---|---|---|---|---|
Experimental | Calculated | Experimental | ||||
Position | Δc, Type | δH (J in Hz) | δC | δH | δC | δH |
1 | 71.6, CH | 4.49 s | 75.1 | 3.94 | 70.8, CH | 4.21 s |
2 | 72.9, CH | 4.19 * | 71.2 | 4.31 | 72.2, CH | 3.96 s |
3 | 119.9, CH | 5.59 s | 126.7 | 5.62 | 118.9, CH | 5.35 s |
4 | n.o. | - | - | 142.4, C | - | |
4a | 62.6, CH | 3.06 d (11.0) | 59.9 | 2.96 | 61.4, CH | 2.58 d (10.6) |
6α | 57.0, CH2 | 4.19 * | 56.4 | 4.03 | 57.0, CH2 | 3.99 d (13.8) |
6β | 57.0, CH2 | 3.71 d (14.1) | 56.4 | 3.57 | 57.0, CH2 | 3.30 d (13.8) |
6a | 127.2, C | - | 129.3 | - | 127.5, C | - |
7 | 111.7, CH | 6.76 s | 107.8 | 6.73 | 111.6, CH | 6.63 s |
8 | 147.8, C | - | 145.2 | - | 146.1, C | - |
9 | 146.8, C | - | 145.4 | - | 145.2, C | - |
10 | 112.7, CH | 6.88 s | 114.2 | 7.07 | 112.4, CH | 6.70 s |
10a | 128.8, C | - | 128.5 | - | 129.1, C | - |
10b | 40.5, CH | 2.76 d (11.1) | 41.6 | 3.05 | 40.2, CH | 2.49 * |
11 | 29.3, CH2 | 2.68 * (2H) | 31.3 | 2.70 | 28.5, CH2 | 2.46 * (2H) |
12α | 54.8, CH2 | 3.40 * | 53.1 | 3.38 | 53.9, CH2 | 3.20 t (8.2) |
12β | 54.8, CH2 | 2.67 * | 53.1 | 2.61 | 53.9, CH2 | 2.19 q (8.4) |
8-OMe | 56.5, CH3 | 3.84 s | 54.5 | 3.97 | 56.2, CH3 | 3.71 s |
CMAE | 2.3 | 0.13 | ||||
Max. outlier | 6.8 | 0.55 |
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Le, N.-T.-H.; De Jonghe, S.; Erven, K.; Vermeyen, T.; Baldé, A.M.; Herrebout, W.A.; Neyts, J.; Pannecouque, C.; Pieters, L.; Tuenter, E. Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis littoralis. Molecules 2023, 28, 3222. https://doi.org/10.3390/molecules28073222
Le N-T-H, De Jonghe S, Erven K, Vermeyen T, Baldé AM, Herrebout WA, Neyts J, Pannecouque C, Pieters L, Tuenter E. Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis littoralis. Molecules. 2023; 28(7):3222. https://doi.org/10.3390/molecules28073222
Chicago/Turabian StyleLe, Ngoc-Thao-Hien, Steven De Jonghe, Kristien Erven, Tom Vermeyen, Aliou M. Baldé, Wouter A. Herrebout, Johan Neyts, Christophe Pannecouque, Luc Pieters, and Emmy Tuenter. 2023. "Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis littoralis" Molecules 28, no. 7: 3222. https://doi.org/10.3390/molecules28073222