One New and Nine Known Flavonoids from Choerospondias axillaries and Their in Vitro Antitumor, Anti-Hypoxia and Antibacterial Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of 1 and Identification of 2–10
Position | 1 ( in CD3OD) | 3 ( in DMSO- d6) | ||
---|---|---|---|---|
δH | δC | δH | δC | |
narigenin | ||||
2 | 5.31 (1H, dd, J = 12.8, 2.8 Hz) | 79.7 | 5.53 (1H, dd, J = 12.4, 3.0 Hz) | 78.6 |
3 | 3.07 (1H, dd, J = 16.8, 12.8 Hz)2.66 (1H, dd, J = 16.8, 2.8 Hz) | 43.3 | Overlapped 2.74 (1H, dd, J = 17.2, 3.0 Hz) | 42.5 |
4 | 197.3 | 196.7 | ||
4a | 102.9 | 102.3 | ||
5 | 164.9 | 163.3 | ||
6 | 5.90 (1H, d, J = 2.0 Hz) | 96.6 | 5.90 (1H, d, J = 2.4 Hz) | 96.4 |
7 | 167.6 | 167.2 | ||
8 | 5.88 (1H, d, J = 2.0 Hz) | 95.8 | 5.89 (1H, d, J = 2.4 Hz) | 95.5 |
8a | 164.3 | 164.0 | ||
1′ | 133.5 | 132.4 | ||
2′ | 7.29 (1H, d, J = 8.4 Hz) | 128.4 | 7.44 (2H, d, J = 8.6 Hz) | 128.6 |
3′ | 7.06 (1H, d, J = 8.4 Hz) | 117.1 | 7.07 (2H, d, J = 8.6 Hz) | 116.7 |
4′ | 158.5 | 158.1 | ||
5′ | 7.06 (1H, d, J = 8.4 Hz) | 117.1 | 7.07 (2H, d, J = 8.6 Hz) | 116.7 |
6′ | 7.29 (1H, d, J = 8.4 Hz) | 128.4 | 7.44 (2H, d, J = 8.6 Hz) | 128.6 |
5-OH | 12.13 (1H, s) | |||
7-OH | 10.82 (1H, s) | |||
glucosyl | ||||
1″ | 4.91 (1H, d, J = 7.6 Hz) | 101.5 | 4.89 (1H, d, J = 7.6 Hz) | 100.8 |
2″ | 3.49–3.54 (1H, m) | 74.3 | 3.13–3.49 (1H, m) | 73.7 |
3″ | 3.49–3.54 (1H, m) | 77.5 | 3.13–3.49 (1H, m) | 77.6 |
4″ | 3.42 (1H, m) | 71.5 | 3.13–3.49 (1H, m) | 70.2 |
5″ | 3.78 (1H, m) | 75.1 | 3.13–3.49 (1H, m) | 77.1 |
6″ | 4.38 (1H, dd, J = 12.0, 8.4 Hz)4.61 (1H, dd, J = 12.0, 2.0 Hz) | 64.4 | 3.13–3.49 (1H, m) 3.70 (1H, dd, J = 10.6, 4.0 Hz) | 61.2 |
galloyl | ||||
1‴ | 120.8 | |||
2‴ | 7.10 (1H, s) | 109.8 | ||
3‴ | 146.0 | |||
4‴ | 139.4 | |||
5‴ | 146.0 | |||
6‴ | 7.10 (1H, s) | 109.8 | ||
7‴ (C=O) | 167.9 |
Position | δH | 1H-1H COSY | δC | HMBC (H→C) | NOESY | ||
---|---|---|---|---|---|---|---|
2(u) | 3.96 (1H, m) | 78.1 | C-3(u), 4(u), 6′(u) | 4(u)-Hb | |||
3(u) | 3.96 (1H, m) | 4(u)-H | 65.5 | C-2(u), 4(u), 1′(u) | 4(u)-Ha, 2′(u)-Ha | ||
4(u) | Ha:2.52 (1H, dd,
J = 9.0,14.4 Hz) Hb:2.92 (1H, dd, J = 5.8,14.4 Hz) | 3(u)-H 3(u)-H | 27.0 | C-2(u), 3(u), 4a(u), 5(u) | 3(u), 4(u)-Hb 2(u), 4(u)-Ha | ||
4a(u) | 99.1 | ||||||
5(u) | 155.0 c | ||||||
6(u) | 5.52 (1H, d, J = 2.6 Hz) b | 8(u) | 94.4 d | C-4a(u), 5(u),7(u), 8(u) | |||
7(u) | 156.4 c | ||||||
8(u) | 5.89 (1H, d, J = 2.6 Hz) b | 6(u) | 95.7 d | C-4a(u), 6(u), 7(u), 8a(u) | |||
8a(u) | 156.7 c | ||||||
1′(u) | 88.5 | ||||||
2′(u) | Ha:2.67 (1H, d,
J = 11.6 Hz) Hb:2.48 (1H, d, J = 11.6 Hz) | 44.3 | C-2(u),1′(u),3′(u),6′(u) | 3(u), 2′(u)-Hb 2′(u)-Ha | |||
3′(u) | 94.0 | ||||||
4′(u) | 192.8 | ||||||
5′(u) | 6.41 (1H, s) | 111.5 | C-2′(u),1′(u),3′(u),6′(u) | ||||
6′(u) | 162.8 | ||||||
2(t) | 4.92 (1H, d, J = 7.5Hz) | 3(t)-H | 82.1 | C-3(t), 4(t), 1′(t), 2′(t),6′(t),8a(t) | 4(t)-Ha | ||
3(t) | 4.11 (1H, td, J = 7.5,5.2 Hz) | 2(t)-H, 4(t)-H | 66.5 | C-4a(t) | 4(t)-Hb | ||
4(t) | Ha:2.59 (1H, dd, J = 7.5,16.4 Hz) Hb:2.85 (1H, dd, J = 5.2,16.4 Hz) | 3(t)-H 3(t)-H | 26.5 | C-2(t), 3(t), 4a(t), 5(t), 8a(t) | 2(t), 4(t)-Hb 3(t), 4(t)-Ha | ||
4a(t) | 102.6 | ||||||
5(t) | 164.9 | ||||||
6(t) | 6.11 (1H, s) | 89.6 | C-5(t), 8(t) | ||||
7(t) | 166.7 | ||||||
8(t) | 104.3 | ||||||
8a(t) | 153.8 | ||||||
1′(t) | 129.9 | ||||||
2′(t) | 6.84 (1H, d, J = 2.2 Hz) | 5′(t) | 113.5 | C-2(t), 4′(t), 6′(t) | 2(t), 3(t) | ||
3′(t) | 145.0 e | ||||||
4′(t) | 145.2 e | ||||||
5′(t) | 6.78 (1H, d, J = 8.0 Hz) | 2′(t), 6′(t) | 115.0 | C-1′(t), 3′(t) | |||
6′(t) | 6.73 (1H, dd, J =2.2,8.0 Hz) | 5′(t) | 118.4 | C-2(t), 2′(t), 4′(t) | 2(t), 3(t) |
2.2. Biological Activities of 1–10
2.2.1. Antitumor Activity
2.2.2. Anti-Hypoxia Effects
Samples | Tested Cells | Cell Viabilities (mean value ± SD%, n = 10) | |
---|---|---|---|
Control Group | Test Group | ||
1 | PC12 | 90.0 ± 6.1 | 131.4 ± 15.3 ** |
2 | ECV304 | 22.6 ± 0.1 | 17.1 ± 1.2 |
3 | ECV304 | 22.6 ± 0.1 | 27.8 ± 1.5 |
4 | ECV304 | 36.1 ± 1.7 | 46.4 ± 1.0 * |
5 | ECV304 | 36.1 ± 1.7 | 51.9 ± 0.9 *** |
6 | PC12 | 82.8 ± 5.3 | 108.1 ± 6.5 ** |
7 | PC12 | 85.9 ± 4.0 | 174.0 ± 8.7 ** |
8 | PC12 | 85.9 ± 4.0 | 155.6 ± 14.4 ** |
9 | PC12 | 90.0 ± 6.1 | 120.8 ± 9.8 ** |
10 | PC12 | 90.0 ± 6.1 | 122.7 ± 7.1 ** |
2.2.3. Anti-Bacterial Activity
2.3. Discussion
3. Experimental Section
3.1. General Experiment Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Physicochemical Properties and Spectra Data
3.5. Bioassays
3.5.1. Cell Line and Cell Culture
3.5.2. Cell Proliferation Assay
3.5.3. Anti-Hypoxia Assay
3.5.4. Antibacterial Effect Test
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Li, C.-W.; Cui, C.-B. One New and Nine Known Flavonoids from Choerospondias axillaries and Their in Vitro Antitumor, Anti-Hypoxia and Antibacterial Activities. Molecules 2014, 19, 21363-21377. https://doi.org/10.3390/molecules191221363
Li C-W, Cui C-B. One New and Nine Known Flavonoids from Choerospondias axillaries and Their in Vitro Antitumor, Anti-Hypoxia and Antibacterial Activities. Molecules. 2014; 19(12):21363-21377. https://doi.org/10.3390/molecules191221363
Chicago/Turabian StyleLi, Chang-Wei, and Cheng-Bin Cui. 2014. "One New and Nine Known Flavonoids from Choerospondias axillaries and Their in Vitro Antitumor, Anti-Hypoxia and Antibacterial Activities" Molecules 19, no. 12: 21363-21377. https://doi.org/10.3390/molecules191221363