Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Methods
2.2. Plant Material
2.3. Extraction and Isolation
2.3.1. Hypersine A
2.3.2. Hypersine B
2.3.3. Hypersine C
2.4. Quantum Chemical Calculation of 13C NMR
2.5. Quantum Chemical Calculation of ECD Spectra
2.6. Single-Crystal X-ray Diffraction Analysis of 2b
2.7. Cell Culture
2.8. MTT Assay
2.9. Western Blotting
2.10. Cell Cycle Analysis
2.11. Statistical Analysis
3. Results
3.1. Isolation of Compounds 1–3
3.2. Structural Elucidation of Compounds 1−3
3.3. Plausible Biosynthetic Pathway to 1–3
3.4. Biological Activity Evaluation of the Isolated Compounds
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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No. | 1a/1b | 2a/2b | 3a/3b | |||
---|---|---|---|---|---|---|
δH (mult, J, Hz) | δC | δH (mult, J, Hz) | δC | δH (mult, J, Hz) | δC | |
1 | 105.6 | 105.5 | 104.9 | |||
2 | 189.4 | 189.3 | 189.3 | |||
3 | 105.0 | 105.0 | 104.8 | |||
4 | 172.7 | 172.7 | 172.8 | |||
5 | 48.8 | 48.8 | 48.7 | |||
6 | 197.3 | 197.3 | 197.2 | |||
7 | 2.90 d (9.6) | 34.8 | 2.90 d (9.6) | 34.8 | 2.90 d (9.6) | 34.8 |
8 | 2.55 dd (9.6, 7.2) | 37.6 | 2.55 t (7.8) | 37.6 | 2.55 t (7.2) | 37.5 |
9 | 86.7 | 86.7 | 86.7 | |||
10 | 1.40 s | 27.4 | 1.40 s | 27.4 | 1.40 s | 27.4 |
11 | α 1.77 m | 40.4 | α 1.76 m | 40.4 | α 1.76 m | 40.3 |
β 1.88 m | β 1.88 m | β 1.88 m | ||||
12 | α 1.61 m | 26.2 | α 1.61 m | 26.2 | α 1.61 m | 26.1 |
β 1.70 m | β 1.70 m | β 1.68 m | ||||
13 | 2.42 t (7.8) | 47.1 | 2.42 t (7.2) | 47.1 | 2.43 t (7.8) | 47.0 |
14 | 38.8 | 38.8 | 38.8 | |||
15 | 1.34 s | 33.5 | 1.35 s | 33.5 | 1.34 s | 33.5 |
16 | 0.80 s | 18.1 | 0.80 s | 18.0 | 0.80 s | 18.0 |
17 | 1.32 s | 24.5 | 1.32 s | 24.1 | 1.32 s | 24.3 |
18 | 1.36 s | 25.2 | 1.36 s | 25.6 | 1.36 s | 25.5 |
1’ | 207.9 | 208.0 | 208.6 | |||
2’ | 3.84 m | 42.1 | 3.83 m | 42.2 | 3.97 m | 35.9 |
3’ | 1.14 d (7.2) | 16.7 | 1.12 d (7.2) | 16.7 | 1.13 d (7.2) | 19.1 |
4’ | α 1.40 overlap | 26.9 | α 1.41 overlap | 26.8 | 1.15 d (7.2) | 19.2 |
β 1.73 m | β 1.74 m | |||||
5’ | 0.90 t (7.2) | 11.9 | 0.93 t (7.2) | 12.0 |
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Liu, X.-Z.; Zhou, M.; Du, C.-C.; Zhu, H.-H.; Lu, X.; He, S.-L.; Wang, G.-H.; Lin, T.; Tian, W.-J.; Chen, H.-F. Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response. Biomedicines 2021, 9, 1473. https://doi.org/10.3390/biomedicines9101473
Liu X-Z, Zhou M, Du C-C, Zhu H-H, Lu X, He S-L, Wang G-H, Lin T, Tian W-J, Chen H-F. Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response. Biomedicines. 2021; 9(10):1473. https://doi.org/10.3390/biomedicines9101473
Chicago/Turabian StyleLiu, Xiang-Zhong, Mi Zhou, Chun-Chun Du, Hong-Hong Zhu, Xi Lu, Shou-Lun He, Guang-Hui Wang, Ting Lin, Wen-Jing Tian, and Hai-Feng Chen. 2021. "Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response" Biomedicines 9, no. 10: 1473. https://doi.org/10.3390/biomedicines9101473