Recent Advances on Biological Activities and Structural Modifications of Dehydroabietic Acid
Abstract
:1. Introduction
2. Bioactivities of Dehydroabietic Acid and Its Derivatives
2.1. Antitumor Activity
2.2. Anti-Inflammatory Activity
2.3. Antibacterial and Antifungal Activities
2.4. Insecticidal Activity
2.5. Antiprotozoal Activity
2.6. Other Activities
3. Structural Modification of Dehydroabietic Acid and Its Derivatives
3.1. Structural Modification at C-18 of Dehydroabietic Acid
3.2. Structural Modification at B Ring of Dehydroabietic Acid
3.3. Structural Modification at C Ring of Dehydroabietic Acid
3.4. Biotransformation of Dehydroabietic Acid
4. Total Synthesis of Dehydroabietic Acid
5. Structure-Activity Relationships of Dehydroabietic Acid and Its Derivatives
6. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
AP-1 | Activating protein-1 |
5-Fu | 5-Fluorouracil |
G6Pase | Glucose-6-Phosphatase |
GS | Glycogen Synthase |
IC50 | Half-inhibitory concentration |
MCP-1 | Monocyte chemoattractant protein-1 |
MIC | Minimum inhibitory concentration |
NF-κB | Nuclear factor-κB |
Nrf2 | Nuclear factor erythroid 2-related factor 2 |
NO | Nitric oxide |
PARP | Poly (ADP-ribose) polymerase |
PPA | Polyphosphoric acid |
PPAR | Peroxisome proliferator-activated receptors |
ROS | Reactive oxygen species |
TAK1 | Transforming growth factor β-activated kinase 1 |
TNF-α | Tumor necrosis factor-α |
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Compound | Bacteria | MIC Value |
---|---|---|
5 | B. subtilis | 4 μg/mL [36] |
5 | S. aureus | 2 μg/mL [36] |
7 | methicillin resistant S. aureus | 32 μg/mL [39] |
8 | LA-MRSA LGA251(ST425-XI) | 3.9 μg/mL [40] |
9 | S. aureus Newman | 0.39–0.78 μg/mL [41] |
10 | NRS-70 | 1.25–1.56 μg/mL [41] |
11 | S. aureus Newman, NRS-1, NRS-70, NRS-100, NRS-108, and NRS-271 | 1.56–3.13 μg/mL [41] |
12 | S. aureus Newman, NRS-70, NRS-108, and NRS-271 | 1.56–3.13 μg/mL [41] |
Compound | Cancer Cell Line | IC50 Value |
---|---|---|
22f | HeLa | 7.76 ± 0.98 μM [64] |
28e | SK-OV-3 | 1.79 ± 0.43 μM [65] |
30n | HeLa | 6.58 ± 1.11 μM [66] |
36w | HeLa | 2.21 ± 0.04 μM [69] |
36w | BEL-7402 | 14.46 ± 0.22 μM [69] |
39j | MGC-803 | 3.82 ± 0.18 μM [70] |
41c | HepG2 | 5.90 ± 0.41 μM [71] |
41k | HepG2 | 6.25 ± 0.37μM [71] |
43b | MCF-7 | 7.00 ± 0.96 μM [72] |
47n | BEL-7402 | 11.23 ± 0.21 μM [73] |
47j | CNE-2 | 8.36 ± 0.14 μM [73] |
63r | HepG2 | 24.41 ± 0.26 μM [81] |
63s | HepG2 | 22.92 ± 0.24 μM [81] |
67g | SMMC-7721 | 1.39 ± 0.13 μM [82] |
67g | HepG2 | 0.51 ± 0.09 μM [82] |
67g | Hep3B | 0.73 ± 0.08 μM [82] |
69p | MDA-MB-231 | 0.7 ± 0.1 μM [84] |
74b | SMMC-7721 | 0.36 ± 0.13 μM [86] |
74e | HepG2 | 0.12 ± 0.03 μM [86] |
77b | SMMC-7721 | 0.72 ± 0.09 μM [87] |
79h | MCF-7 | 0.87 ± 0.18 μM [88] |
80j | SMMC-7721 | 0.08 ± 0.01 μM [89] |
84a | HCT-116 | 1.18 ± 0.52 μM [90] |
Compound | Bacteria | MIC Value |
---|---|---|
33e | B. subtilis | 1.9 μg/mL [68] |
57j | S. aureus NRS-70, NRS-100, NRS-108 and NRS-271 | 1.56–2.5 μg/mL [78] |
69o | S. aureus, E. coli and P. fluorescens | 1.6 μg/mL [83] |
Compound | Human Normal Cell Line | IC50 Value |
---|---|---|
22f | HL-7702 | 53.78 ± 1.4 μM [64] |
36w | HL-7702 | 66.08 ± 1.84 μM [69] |
39j | LO2 | >100 μM [70] |
41c, 41k | HL-7702 | >100 μM [71] |
47j | HL-7702, NP69 | >100 μM [73] |
47n | NP69 | >100 μM [73] |
47n | HL-7702 | 88.18± 0.23 μM [73] |
67g | QSG-7701 | 12.52 ± 0.58 μM [80] |
74b | LO2 | 3.89 ± 0.29 μM [86] |
74e | LO2 | 3.02 ± 0.21 μM [86] |
77b | LO2 | 11.09 ± 0.57 μM [87] |
79h | LO2 | 42.83 ± 3.18 μM [88] |
80j | QSG-7701 | 5.82 ± 0.38 μM [89] |
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Hao, M.; Xu, J.; Wen, H.; Du, J.; Zhang, S.; Lv, M.; Xu, H. Recent Advances on Biological Activities and Structural Modifications of Dehydroabietic Acid. Toxins 2022, 14, 632. https://doi.org/10.3390/toxins14090632
Hao M, Xu J, Wen H, Du J, Zhang S, Lv M, Xu H. Recent Advances on Biological Activities and Structural Modifications of Dehydroabietic Acid. Toxins. 2022; 14(9):632. https://doi.org/10.3390/toxins14090632
Chicago/Turabian StyleHao, Meng, Jianwei Xu, Houpeng Wen, Jiawei Du, Shaoyong Zhang, Min Lv, and Hui Xu. 2022. "Recent Advances on Biological Activities and Structural Modifications of Dehydroabietic Acid" Toxins 14, no. 9: 632. https://doi.org/10.3390/toxins14090632