Research Progress of Natural Matrine Compounds and Synthetic Matrine Derivatives
Abstract
:1. Introduction
2. Novel Matrine-Type Alkaloids
3. Modification on the D-Ring
3.1. Modification at Position C-13
Compound | Activity Test | Method | Result | References |
---|---|---|---|---|
55–56 | Antiproliferative activities assays against the human cancer cell lines Hela229 | MTT assay | The IC50 values of sophorine, matrine, compounds 55 and 56 against Hela229 cells at 72 h were 1.50 ± 0.80, 1.53 ± 0.32, 0.42 ± 0.12 and 0.12 ± 0.03 mM, respectively | [54] |
WM622 | Antiproliferative activity against hepatocellular carcinoma cells | MTT assay | The IC50 of WM622 was 34 µM for LM3, and 41 µM for Hep3B, respectively. The IC50 of matrine was 801 µM for LM3, and 845 µM for Hep3B, respectively. | [55] |
Inhibition on migration of HCC cells | Transwell chamber assay | WM622 can inhibit the migration activity of HCC cells and the effect was better than matrine | [55] | |
Inducing apoptosis of HCC cells | Flow cytometry | The apoptosis rate of LM3 cells were 5.68 ± 0.17%, 9.48 ± 0.43%, 12.2 ± 0.30% and 16.43 ± 0.28% in response to treatment with 0, 10, 20 and 30 µM of WM622, respectively. The apoptosis rate of Hep3B cells were 4.70 ± 1.52%, 7.56 ± 1.42%, 9.52 ± 0.98% and 14.20 ± 0.60% in response to treatment with 0, 10, 20 and 30 µM of WM622, respectively | [55] | |
Growth inhibition of HCC xenografts in nude mice | Balb/c nude mice | The effect of WM622 on tumor growth was stronger than that of 5-Fu; Western experiments showed that expression levels of p-PI3K (Tyr458), p-AKT(Thr308), p-EGFR(Tyr1068) and p-GSK3β(Ser9) were down-regulated and the level of PTEN was up-regulated dose dependently | [55] | |
MASM | Effects of MASM on cell viability and cellular toxicity | MTT assay LDH assay | MASM induced a dose- and time-dependent inhibitory effect on the viability of A549, MCF-7, MDA-MB-231 and Hela cells | [57] |
Analysis for apoptosis | Flow cytometry LDH assay | At the same dosage MASM induced more apoptosis in MDA-MB-231 and Hela cells than in A549 and MCF-7; MASM induce apoptosis in a dose-dependent manner through caspase 3-dependent manner (in A549, MDA-MB-213 and Hela) and caspase 3-independent manner (in MCF-7, which is caspase 3 deficient) | [57] | |
The expression levels of p-Akt, Akt, p-Erk1/2, Erk1/2, p-p38, and p38 were detected by Western blot | Western Blot | MASM inhibited Akt phosphorylation in all four cell types in a dose dependent manner. MASM promotes the phosphorylation of Erk1/2 and p38. | [57] | |
Apoptosis of MDA-MA-231 in the presence of ROS scavher N-acetylcysteine | Western Blot | Western blot analysis showed that the activation of Erk1/2 and p38by MASM and the accumulation of LC3-II were also inhibited by NAC | [57] | |
M-54 | The cell differentiation effect of M-54 on BMMCs and RAW264.7 cells | TRAR staining | The number of osteoclasts in BMMCs and RAW264.7 cells treated with M-54 decreased significantly | [60] |
The effect of M-54 on RPS5 PI3K-AKT, NF-κB, and MAPK expression in RANKL-induced osteoclasts | Western blot | Osteoclasts treated with M-54 could increase the expression of RPS5 in a dose-dependent manner, and significantly inhibit phosphorylation of Akt, P65, IKb, ERK, JNK, and P38. | [60] | |
Inhibition of bone loss induced by ovariectomy in mice | OVX mouse Micro-CT Analysis | Histological analysis showed that M54 prevented the loss of bone trabeculae | [60] | |
57–58 | Inhibition of TGF-β1-Induced Collagen Accumulation | Sircol collagen assay | The IC50 values of compounds 57a–57d and 58a–58n and matrine on the total collagen accumulation of TGF-β1-stimulated MRC-5 cells were 65.3 ± 4.2, 92.1 ± 1.9, 255.8 ± 22.1, 138.4 ± 9.8, 28.3 ± 3.9, 39.0 ± 0.6, 44.7 ± 3.6, 4.3 ± 0.4, 68.1 ± 5.5, 3.3 ± 0.3, 6.5 ± 1.2, 72.1 ± 4.0, 14.5 ± 1.0, 16.7 ± 3.5, 23.1 ± 5.3, 27.0 ± 1.4, 19.3 ± 2.2, 69.5 ± 8.2, 878 ± 68 µM, respectively | [61] |
58f | Inhibition Effects of Expression Levels of extracellular matrix Proteins by 58f | Immunofluorescence Assay | Compared with the TGF-β1 stimulation group, the 58f treatment group reduced fibronectin expression levels by 40% | [61] |
Inhibition Effects against Fibroblast-to-Myfibroblast Transition by 58f | Immunofluorescence Assay | The conversion of fibroblasts into myofibroblasts after treatment with compound 58f was interrupted, and the expression levels of α-SMA and S100A4 were reduced from 774.9% and 537.7% to 45.8% and 17.7%, respectively | [61] | |
Inhibition Effects against Smad-Mediated Signaling by 58f | Immunofluorescence Assay | 58f could significantly inhibit the cytoplasm-to-nuclear translocation of Smad2/3. | [61] | |
Inhibition Effects against TGF-β1 Induced Migration of MRC-5 Cells by 58f | Scratch Assay | The wound closure area of TGF-β1-stimulated MRC-5 fibroblasts reached 85% within 24 h, 10 μM compound 58f treated was only 37.7%, 1000 μM matrine treated was 56.6%. | [61] | |
WM1 series | Effects of WM1 series on EGFP expression in cell models HepG2-Sur5P-EGFP-Sur3U | Fluorescence microscope observation | WM-127 had the strongest inhibitory effect on ECFP in cell models HepG2-Sur5P-EGFP-Sur3U | [63] |
WM127 | Anti-proliferative activity of WM127 on HCC cells | MTT assay | The IC50 values of WM127 against WRL-68, Huh-7 and HepG2 cells were 105.80 ± 5.4, 60.04 ± 2.47 and 52.59 ± 4.29 μg/mL, respectively, and the proliferation of HepG2 and Huh7 cells was inhibited in a dose—and time-dependent manner | [63] |
Effects of WM127 on cell cycle and apoptosis | Flow cytometry | MW127 induced obvious G2 phase arrest in HepG2 and Huh-7 cells, but not in WRL-68 cells; Compared with the control group, the apoptosis rate of HepG2 and Huh-7 cells treated with WM127 was significantly increased, but the apoptosis rate of WRL-68 cells was not significantly increased | [63] | |
Effect of WM127 on Survivin/β-catenin pathway in HCC cells and Bax | Western blot; immunohistochemistry | The expression of b-catenin was down-regulated dose-dependently, being consistent with the expression of Survivin, the expression level of Bax was up-regulated in the WM-127-treated HepG2 and Huh-7 cells | [63] |
3.2. Modification at Position C-14
Compound | Activity Test | Method | Result | References |
---|---|---|---|---|
YYJ18 | Antiproliferation activity of YYJ18 on CNE2/5–8F cell | CCK8 assay Plate cloning experiment | The OD value of nasopharyngeal carcinoma cell proliferation after YYJ18 treatment was significantly lower than that in control group, and showed a time-dose dependence, the number of clone formation in the drug treatment group was significantly lower than that in the control group, and the number of clone formation was negatively correlated with the concentration of YYJ18. | [66] |
Effect of YYJ18 on migration ability of CNE2/5–8F cell | Scratch Assay | With the increase of YYJl8 concentration, the migration distance of nasopharyngeal carcinoma cells decreased significantly and showed a negative correlation of concentration | [66] | |
Effect of YYJ18 on invasion ability of CNE2/5–8F cell | Teanswell cell invasion test | The invasion ability of CNE2/5–8F cells treated with YYJ18 was significantly weaker than that of the control group, and with the increase of YYJ18 concentration, the number of transmembrane cells was inhibited, showing a negative correlation of concentration. | [66] | |
Effect of YYJ18 on tumor formation in nude mice | Pharmacodynamic experiment | The tumor growth rate of nude mice inoculated with CNE2 cells was significantly lower than that of the control group after intraperitoneal injection of YYJ18 | [66] | |
Effect of YYJ18 on epithelial mesenchymal transformation of nasopharyngeal carcinoma cells | Western blot | In nasopharyngeal carcinoma CNE2/5–8F cells treated with YYJl8, N-cadherin and Vimentin proteins positively correlated with EMT were down-regulated, while e-cadherin proteins negatively correlated with EMT were up-regulated | [66] | |
Effect of YYJ18 on PI3K/AKT signaling pathway in nasopharyngeal carcinoma cells | Western blot | The expression of p-Akt protein AKT, a key protein in the P13K/AKT signaling pathway, was down-regulated in nasopharyngeal carcinoma CNE2/5–8F cells after YYJl8 treatment, while the expression of total AKT protein was not significantly changed | [66] | |
59–62 | Cytotoxicity of compound 59–62 to SMMC-7721, A549 and CNE2 cells | MTT assay | The IC50 values of all matrine derivatives against SMMC-7721, A549 and CNE2 cells were lower than that of matrine, among which 59F and 60u showed the strongest activity with IC50 values of 4.65 ± 0.23, 8.05 ± 0.56, 3.55 ± 0.18 and 3.95 ± 0.34, 4.96 ± 0.54, 3.42 ± 0.23 μM, respectively | [68] |
Effects of compounds 59F and 60u on apoptosis of CNE2 and SMMC-7721 cells | Flow cytometry | The percentage of apoptotic cells in CNE2 increased from 4.93% (control) to 11.96% (5 μM), 34.04% (10 μM) and 50.50% (30 μM) respectively after treatment with different concentrations of compound 59F for 24 h. The percentage of apoptotic cells in SMMC-7721 increased from 2.60% (control) to 19.93% (5 μM), 53.58% (10 μM) and 61.50% (30 μM), respectively, the percentage of apoptotic cells of in CNE2 significantly increased from 5.29% (control) to 17.52% (10 μM), 38.60% (20 μM) and 74.20% (50 μM) respectively after treatment with different concentrations of compound 60u for 24 h. The percentage of apoptotic cells in SMMC-7721 increased from 2.60% (control) to 39.00% (10 μM), 58.80% (20 μM) and 95.00% (50 μM), respectively. The percentage of G2/M phase in CNE2 cells treated with 59F gradually increased from 19.8% (control) to 29.5% (5 μM), 89.4% (10 μM) and 81.1% (30 μM), the percentage of G2/M phase in SMMC-7721 cells treated with 59F increased from 18.4% (control) to 24.1% (5 μM), 78.9% (10 μM) to 79.1% (30 μM). | [68] | |
63a–63ac | Antiproliferation activity of compound 63–64 | MTT assay | The IC50 values of compounds 63a, 63c, 63d, 63e, 63f, 63o, 63t, 63v, 63w, 63x, 63z, 63aa, 63ab against A549 cells are 48.3 ± 3.4, 42.6 ± 2.3, 26.6 ± 2.4, 37.7 ± 2.5, 42.7 ± 4.9, 45.7 ± 3.843.0 ± 3.3, 48.1 ± 4.5, 49.6 ± 3.8, 38.7 ± 2.7, 37.8 ± 1.3, 11.4 ± 1.8, 38.8 ± 1.1 μM, respectively. All others are greater than 100 μM. The IC50 values of compounds 63a, 63d, 63e, 63h, 63j, 63o, 63t, 63v, 63x, 63z, 63aa,63ab against HepG2 cells are 35.4 ± 4.4, 24.6 ± 3.2, 26.1 ± 4.1, 45.6 ± 3.7, 36.3 ± 2.6, 49.7 ± 4.3, 37.5 ± 3.4, 45.8 ± 3.8, 39.2 ± 3.1, 34.6 ± 3.5, 9.1 ± 1.2, 25.1 ± 2.9 μM, respectively. All others are greater than 100 μM. | [69] |
63aa | Antiproliferation activity of compound 63–64 against HepG2, SMMC-7721, A549, and CNE2 cells | MTT assay | The IC50 values of compound 3aa against HepG2, SMMC-7721, A549, and CNE2 cells are 9.1 ± 1.2, 9.0 ± 1.4, 11.4 ± 1.8, 7.8 ± 0.8 μM, respectively. The IC50 values of matrine against HepG2, SMMC-7721, A549, and CNE2 cells are 4178 ± 395, 5591 ± 521, 5725 ± 602, 5278 ± 498 μM, respectively. The IC50 values of cisplatin against HepG2, SMMC-7721, A549, and CNE2 cells are 8.4 ± 0.5, 6.0 ± 0.4, 8.5 ± 0.5, 3.8 ± 0.2 μM, respectively. | [69] |
Effects of compound 63aa on cell cycle of CNE2 and SMMC-7721 | Flow cytometry | The percentage of G2/M phase in SMMC-7721 gradually increased from 19.3% (control) to 19.0% (10 μM), 20.2% (20 μM) and 26.5% (50 μM). Similarly, the percentage of G2/M phase in CNE2 cells increased from 22.0% (control) to 28.2% (10 μM), 31.0% (20 μM) to 34.4% (50 μM). | [69] | |
Effects of compound 63aa on apoptosis of CNE2 and SMMC-7721 | Flow cytometry | The percentage of apoptotic cells in CNE2 significantly increased from 2.24% (control) to 24.54% (10 μM), 31.50% (20 μM) and 49.60% (50 μM) after treatment with different concentrations of compound 63aa for 24 h. Similarly, the percentage of apoptotic cells in SMMC-7721 increased from 2.60% (control) to 19.93% (10 μM), 53.58% (20 μM) and 61.50% (50 μM). | [69] | |
Effects of compound 63aa on the expression of Bax, Bcl-2 and cleavage of caspase-3 | Western Blot | 63aa significantly increased the relative levels of proapoptotic Bax expression but reduced the levels of antiapoptotic Bcl-2 expression in a dose-dependent manner. | [69] | |
64a–64h | Cytotoxicity of compound 64a–64h to three NPC cell lines (CNE2, HONE1, and HK-1) and CDDP resistance cell line (CNE2/CDDP) | MTT assay | 8 derivatives displayed better antiproliferative effects (IC50 ranging from 35 to 700 µM) than the parent compound matrine (IC50 more than 1000 µM). Notably, compound 3f showed the most prominent proliferation inhibition effects in NPC and NPC/CDDP resistant cells with IC50 ranging from 30 to 100 µM | [70] |
Combined Inhibitory Effects Evaluation of 8 Derivatives with CDDP | MTT assay | Only compound 64f could increase the inhibitory effects of CDDP against CNE2/CDDP cells | [70] | |
Synergistic Inhibitory Effect Evaluation of Compound 3f with CDDP | MTT assay | In CNE2/CDDP cells treated simultaneously with 64f and CDDP, the CI values were less than 1, indicating synergism between 64f and CDDP | [70] | |
Effect of compound 64f combined with CDDP on apoptosis of CNE2/CDDP cells | Apoptosis kit | Combined treatment with CDDP (4 µg/mL) and 3f (40 µM) increased significant cell apoptosis compared with CDDP (15.53 ± 1.61 vs. 7.58 ± 0.82) or 64f (15.53 ± 1.61 vs. 9.97 ± 1.36) treatment alone | [70] | |
In vivo Anticancer Evaluation of Compound 64f | BALB/C nude mice | The combined treatment of CDDP with 64f significantly reduced tumor volume and weight compared with CDDP or 64f treatment alone | [70] | |
65a–65i | Inhibitory activity of compound 65a–65i against HepG2 and HeLa | MTT assay | The IC50 values of compounds 64b, 64c, 64d, 64e, 64i and camptothecin against HepG2 were 96, 97, 11, 51, 86 and 39 μM, respectively. All others are greater than 100 μM. The IC50 values of compounds 64b, 64d, 64e and camptothecin against HepG2 were 93, 23, 33 and 12 μM, respectively. All others are greater than 100 μM. | [71] |
3.3. Modification at Position C-15
3.4. D Ring Opening and Fusion
4. Conclusions
5. Challenges and Prospects
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
Abbreviations
AMPK | adenosine 5′-monophosphate-activated protein kinase |
APAP | acetaminophen |
Bax | Bcl-2 Assaciated X protein |
Bcl-2 | B-cell lymphoma-2 |
CDDP | cis-diamminedichloroplatinum |
COX-2 | cyclooxygenase-2 |
EMT | epithelial-mesenchymal transition |
GSK3β | recombinant Glycogen Synthase Kinase 3 Beta |
IL-6 | interleukin-6 |
iNOS | inducible Isoform of Nitric Oxide Synthase |
LPS | lipopolysaccharide |
MTT | 3-(4,5)-dimethylthiahiazo(-z-y1)-3,5-di-phenytetrazoliumromide |
PI3K | phosphatidylinositol3-kinase |
ROS | reactive oxygen species |
RPS5 | ribosomal protein S5 |
TGF-β1 | transforming growth factor beta 1 |
TNF-α | tumor necrosis factor-α |
References
- Wang, R.; Liu, H.; Shao, Y.; Wang, K.; Yin, S.; Qiu, Y.; Wu, H.; Liu, E.; Wang, T.; Gao, X.; et al. Sophoridine Inhibits Human Colorectal Cancer Progression via Targeting MAPKAPK2. Mol. Cancer Res. 2019, 17, 2469–2479. [Google Scholar] [CrossRef] [Green Version]
- Tang, S.; Peng, Z.G.; Li, Y.H.; Zhang, X.; Fan, T.Y.; Jiang, J.D.; Wang, Y.X.; Song, D.Q. Synthesis and biological evaluation of tricyclic matrinic derivatives as a class of novel anti-HCV agents. Chem. Cent. J. 2017, 11, 94. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ren, G.; Ding, G.; Zhang, H.; Wang, H.; Jin, Z.; Yang, G.; Han, Y.; Zhang, X.; Li, G.; Li, W. Antiviral activity of sophoridine against enterovirus 71 in vitro. J. Ethnopharmacol. 2019, 236, 124–128. [Google Scholar] [CrossRef] [PubMed]
- Chao, F.; Wang, D.E.; Liu, R.; Tu, Q.; Liu, J.J.; Wang, J. Synthesis, characterization and activity evaluation of matrinic acid derivatives as potential antiproliferative agents. Molecules 2013, 18, 5420–5433. [Google Scholar] [CrossRef] [PubMed]
- Jia, F.; Zhou, Q.; Li, X.; Zhou, X. Total alkaloids of Sophora alopecuroides and matrine inhibit auto-inducer 2 in the biofilms of Staphylococcus epidermidis. Microb. Pathog. 2019, 136, 103698. [Google Scholar] [CrossRef]
- Li, X.; Tang, Z.; Wen, L.; Jiang, C.; Feng, Q. Matrine: A review of its pharmacology, pharmacokinetics, toxicity, clinical application and preparation researches. J. Ethnopharmacol. 2021, 269, 113682. [Google Scholar] [CrossRef]
- Li, L.; Qi, F.; Wang, K. Matrine Restrains Cell Growth and Metastasis by Up-Regulating LINC00472 in Bladder Carcinoma. Cancer Manag. Res. 2020, 12, 1241–1251. [Google Scholar] [CrossRef] [Green Version]
- Guo, S.; Chen, Y.; Pang, C.; Wang, X.; Shi, S.; Zhang, H.; An, H.; Zhan, Y. Matrine is a novel inhibitor of the TMEM16A chloride channel with antilung adenocarcinoma effects. J. Cell Physiol. 2019, 234, 8698–8708. [Google Scholar] [CrossRef]
- Cheng, Y.; Yu, C.; Li, W.; He, Y.; Bao, Y. Matrine Inhibits Proliferation, Invasion, and Migration and Induces Apoptosis of Colorectal Cancer Cells Via miR-10b/PTEN Pathway. Cancer Biother. Radiopharm. 2022, 37, 871–881. [Google Scholar] [CrossRef]
- Li, Q.; Huang, H.; He, Z.; Sun, Y.; Tang, Y.; Shang, X.; Wang, C. Regulatory effects of antitumor agent matrine on FOXO and PI3K-AKT pathway in castration-resistant prostate cancer cells. Sci. China Life Sci. 2018, 61, 550–558. [Google Scholar] [CrossRef]
- Li, X.; Liang, T.; Chen, S.S.; Wang, M.; Wang, R.; Li, K.; Wang, J.C.; Xu, C.W.; Du, N.; Qin, S.; et al. Matrine suppression of self-renewal was dependent on regulation of LIN28A/Let-7 pathway in breast cancer stem cells. J. Cell Biochem. 2020, 121, 2139–2149. [Google Scholar] [CrossRef] [PubMed]
- Lin, S.; Zhuang, J.; Zhu, L.; Jiang, Z. Matrine inhibits cell growth, migration, invasion and promotes autophagy in hepatocellular carcinoma by regulation of circ_0027345/miR-345-5p/HOXD3 axis. Cancer Cell Int. 2020, 20, 246. [Google Scholar] [CrossRef]
- Li, Y.H.; Tang, S.; Li, Y.H.; Cheng, X.Y.; Zhang, X.; Wang, Y.X.; Su, F.; Song, D.Q. Novel 12N-substituted matrinanes as potential anti-coxsackievirus agents. Bioorg. Med. Chem. Lett. 2017, 27, 829–833. [Google Scholar] [CrossRef] [PubMed]
- Wang, X.; Lin, H.; Zhang, R. The Clinical Efficacy and Adverse Effects of Interferon Combined with Matrine in Chronic hepatitis B: A Systematic Review and Meta-Analysis. Phytother. Res. 2017, 31, 849–857. [Google Scholar] [CrossRef]
- Sun, D.; Wang, J.; Yang, N.; Ma, H. Matrine suppresses airway inflammation by downregulating SOCS3 expression via inhibition of NF-κB signaling in airway epithelial cells and asthmatic mice. Biochem. Biophys. Res. Commun. 2016, 477, 83–90. [Google Scholar] [CrossRef] [PubMed]
- Lu, Q.; Lin, X.; Wu, J.; Wang, B. Matrine attenuates cardiomyocyte ischemia-reperfusion injury through activating AMPK/Sirt3 signaling pathway. J. Recept. Signal Transduct. Res. 2021, 41, 488–493. [Google Scholar] [CrossRef]
- Liu, F.; Li, Y.; Yang, Y.; Li, M.; Du, Y.; Zhang, Y.; Wang, J.; Shi, Y. Study on mechanism of matrine in treatment of COVID-19 combined with liver injury by network pharmacology and molecular docking technology. Drug Deliv. 2021, 28, 325–342. [Google Scholar] [CrossRef]
- Li, S.; Liu, X.; Chen, X.; Bi, L. Research Progress on Anti-Inflammatory Effects and Mechanisms of Alkaloids from Chinese Medical Herbs. Evid. Based Complement. Altern. Med. 2020, 2020, 1303524. [Google Scholar] [CrossRef] [Green Version]
- Zhang, H.; Chen, L.; Sun, X.; Yang, Q.; Wan, L.; Guo, C. Matrine: A Promising Natural Product with Various Pharmacological Activities. Front. Pharmacol. 2020, 11, 588. [Google Scholar] [CrossRef]
- Li, P.; Lei, J.; Hu, G.; Chen, X.; Liu, Z.; Yang, J. Matrine Mediates Inflammatory Response via Gut Microbiota in TNBS-Induced Murine Colitis. Front. Physiol. 2019, 10, 28. [Google Scholar] [CrossRef] [Green Version]
- Zhang, X.; Hu, C.; Zhang, N.; Wei, W.Y.; Li, L.L.; Wu, H.M.; Ma, Z.G.; Tang, Q.Z. Matrine attenuates pathological cardiac fibrosis via RPS5/p38 in mice. Acta Pharmacol Sin. 2021, 42, 573–584. [Google Scholar] [CrossRef] [PubMed]
- Wang, H.Y.; Li, Y.X.; Dun, L.L.; Xu, T.T.; Hao, Y.J.; Liu, H.Y.; Ma, L.; Jiang, Y.X.; Wang, Y.R.; Yu, J.Q. Antinociceptive effects of matrine on neuropathic pain induced by chronic constriction injury. Pharm. Biol. 2013, 51, 844–850. [Google Scholar]
- Khan, A.; Shal, B.; Naveed, M.; Nasir, B.; Irshad, N.; Ali, H.; Khan, S. Matrine alleviates neurobehavioral alterations via modulation of JNK-mediated caspase-3 and BDNF/VEGF signaling in a mouse model of burn injury. Psychopharmacology 2020, 237, 2327–2343. [Google Scholar] [CrossRef] [PubMed]
- Wu, J.; Hu, G.; Dong, Y.; Ma, R.; Yu, Z.; Jiang, S.; Han, Y.; Yu, K.; Zhang, S. Matrine induces Akt/mTOR signalling inhibition-mediated autophagy and apoptosis in acute myeloid leukaemia cells. J. Cell Mol. Med. 2017, 21, 1171–1181. [Google Scholar] [CrossRef]
- Xiong, X.Y.; Yu, H.J.; Nan, Y.F. A Highly Sensitive Chemiluminescence Method and Application in Rapid Pharmacokinetic Study of Matrine in Rat Plasma. Curr. Pharm. Anal. 2017, 13, 452–461. [Google Scholar] [CrossRef]
- Nie, J.J.; Chen, F.; Wang, F.W.; Luo, W.; Shen, X. Pharmacokinetics and bioavailability of matrine in rats by UPLC-MS/MS. Latin Am. J. Pharm. 2020, 39, 612–616. [Google Scholar]
- Gu, Y.; Lu, J.; Sun, W.; Jin, R.; Ohira, T.; Zhang, Z.; Tian, X. Oxymatrine and its metabolite matrine contribute to the hepatotoxicity induced by radix Sophorae tonkinensis in mice. Exp. Ther. Med. 2019, 17, 2519–2528. [Google Scholar] [CrossRef] [Green Version]
- Lu, Z.G.; Li, M.H.; Wang, J.S.; Wei, D.D.; Liu, Q.W.; Kong, L.Y. Developmental toxicity and neurotoxicity of two matrine-type alkaloids, matrine and sophocarpine, in zebrafish (Danio rerio) embryos/larvae. Reprod. Toxicol. 2014, 47, 33–41. [Google Scholar] [CrossRef]
- Wang, X.P.; Yang, R.M. Movement disorders possibly induced by traditional Chinese herbs. Eur. J. Neurol. 2003, 50, 153–159. [Google Scholar] [CrossRef]
- Cai, L.Y.; Wu, L.L.; Yu, X.M.; Liu, J.J.; Han, W.C.; Wei, Q.; Tang, L. The absorption and metabolism of oxymatrine in rat intestine. Acta Pharm. Sin. 2015, 50, 1336–1341. [Google Scholar]
- Li, S.S.; Li, Z.; Cheng, T.M.; Su, Z.; Wei, J.R. Contact lethal activity of four environmental friendly pesticides to rhagoletis batava obseuriosa diptera: Tephritidae) adults, a serious fruit fly of seabuckthorn. For. Res. 2018, 31, 98–104. [Google Scholar]
- Huang, J.; Xu, H. Matrine: Bioactivities and Structural Modifications. Curr. Top. Med. Chem. 2016, 16, 3365–3378. [Google Scholar] [CrossRef] [PubMed]
- Cai, X.H.; Guo, H.; Xie, B. Structural Modifications of Matrine-Type Alkaloids. Mini Rev. Med. Chem. 2018, 18, 730–744. [Google Scholar] [CrossRef]
- Yong, J.; Wu, X.; Lu, C. Anticancer Advances of Matrine and Its Derivatives. Curr. Pharm. Des. 2015, 21, 3673–3680. [Google Scholar] [CrossRef] [PubMed]
- Rashid, H.U.; Xu, Y.; Muhammad, Y.; Wang, L.; Jiang, J. Research advances on anticancer activities of matrine and its derivatives: An updated overview. Eur. J. Med. Chem. 2019, 161, 205–238. [Google Scholar] [CrossRef]
- Wu, L.; Wang, G.; Liu, S.; Wei, J.; Zhang, S.; Li, M.; Zhou, G.; Wang, L. Synthesis and biological evaluation of matrine derivatives containing benzo-α-pyrone structure as potent anti-lung cancer agents. Sci. Rep. 2016, 6, 35918. [Google Scholar] [CrossRef]
- Wu, L.; Liu, S.; Wei, J.; Li, D.; Liu, X.; Wang, J.; Wang, L. Synthesis and biological evaluation of matrine derivatives as anti-hepatocellular cancer agents. Bioorg. Med. Chem. Lett. 2016, 26, 4267–4271. [Google Scholar] [CrossRef]
- Jiang, L.; Wu, L.; Yang, F.; Almosnid, N.; Liu, X.; Jiang, J.; Altman, E.; Wang, L.; Gao, Y. Synthesis, biological evaluation and mechanism studies of matrine derivatives as anticancer agents. Oncol. Lett. 2017, 14, 3057–3064. [Google Scholar] [CrossRef] [Green Version]
- He, H.; Qin, X.; Dong, F.; Ye, J.; Xu, C.; Zhang, H.; Liu, Z.; Lv, X.; Wu, Y.; Jiang, X.; et al. Synthesis, characterization of two matrine derivatives and their cytotoxic effect on Sf9 cell of Spodoptera frugiperda. Sci. Rep. 2020, 10, 17999. [Google Scholar] [CrossRef]
- Xu, J.; Sun, Z.; Hao, M.; Lv, M.; Xu, H. Evaluation of biological activities, and exploration on mechanism of action of matrine-cholesterol derivatives. Bioorg. Chem. 2020, 94, 103439. [Google Scholar] [CrossRef]
- Kordestani, M.; Mahdian, K.; Baniameri, V.; Garjan, A.S. Proteus, Matrine, and Pyridalyl Toxicity and Their Sublethal Effects on Orius laevigatus (Hemiptera: Anthocoridae). J. Econ. Entomol. 2022, 115, 573–581. [Google Scholar] [CrossRef] [PubMed]
- Xu, J.; Lv, M.; Xu, H. The Advances in Bioactivities, Mechanisms of Action and Structural Optimizations of Matrine and its Derivatives. Mini Rev. Med. Chem. 2022, 22, 1716–1734. [Google Scholar] [PubMed]
- Zhang, Y.B.; Luo, D.; Yang, L.; Cheng, W.; He, L.J.; Kuang, G.K.; Li, M.M.; Li, Y.L.; Wang, G.C. Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Antiviral Activities against the Hepatitis B Virus. J. Nat. Prod. 2018, 81, 2259–2265. [Google Scholar] [CrossRef] [PubMed]
- Fan, C.L.; Zhang, Y.B.; Chen, Y.; Xie, P.; Wang, G.C.; Tian, H.Y.; Li, Y.L.; Huang, X.J.; Zhang, X.Q.; Li, Z.Y.; et al. Alopecuroides A-E, Matrine-Type Alkaloid Dimers from the Aerial Parts of Sophora alopecuroides. J. Nat. Prod. 2019, 82, 3227–3232. [Google Scholar] [CrossRef]
- Wang, X.F.; Zhu, Z.; Hao, T.T.; Fang, Q.Q.; Jiang, K.; Qu, S.J.; Zuo, J.P.; Zhu, W.; He, S.J.; Tan, C.H. Alopecines A-E, five chloro-containing matrine-type alkaloids with immunosuppressive activities from the seeds of Sophora alopecuroides. Bioorg. Chem. 2020, 99, 103812. [Google Scholar] [CrossRef]
- Li, J.C.; Dai, W.F.; Zhou, X.Q.; Rao, K.R.; Zhang, Z.J.; Liu, D.; Chen, X.Q.; Li, R.T.; Li, H.M. Matrine-Type Alkaloids from the Seeds of Sophora alopecuroides and Their Potential Anti-inflammatory Activities. Chem. Biodivers. 2021, 18, e2001066. [Google Scholar] [CrossRef]
- Tang, Q.; Luo, D.; Lin, D.C.; Wang, W.Z.; Li, C.J.; Zhuo, X.F.; Wu, Z.N.; Zhang, Y.B.; Wang, G.C.; Li, Y.L. Five matrine-type alkaloids from Sophora tonkinensis. J. Nat. Med. 2021, 75, 682–687. [Google Scholar] [CrossRef] [PubMed]
- Li, J.C.; Dai, W.F.; Liu, D.; Zhang, Z.J.; Jiang, M.Y.; Rao, K.R.; Li, R.T.; Li, H.M. Quinolizidine alkaloids from Sophora alopecuroides with anti-inflammatory and anti-tumor properties. Bioorg. Chem. 2021, 110, 104781. [Google Scholar] [CrossRef]
- Luo, D.; Lin, Q.; Tan, J.L.; Zhao, H.Y.; Feng, X.; Chen, N.H.; Wu, Z.N.; Fan, C.L.; Li, Y.L.; Ding, W.L.; et al. Water-soluble matrine-type alkaloids with potential anti-neuroinflammatory activities from the seeds of Sophora alopecuroides. Bioorg. Chem. 2021, 116, 105337. [Google Scholar] [CrossRef]
- Luo, D.; Tu, Z.; Yin, W.; Fan, C.; Chen, N.; Wu, Z.; Ding, W.; Li, Y.; Wang, G.; Zhang, Y. Uncommon Bis-Amide Matrine-type Alkaloids from Sophora alopecuroides With Anti-inflammatory Effects. Front. Chem. 2021, 9, 740421. [Google Scholar] [CrossRef]
- Luo, D.; Chen, N.H.; Wang, W.Z.; Zhang, J.H.; Li, C.J.; Zhuo, X.F.; Tu, Z.C.; Wu, Z.N.; Fan, C.L.; Zhang, H.P.; et al. Structurally Diverse Matrine-Based Alkaloids with Anti-inflammatory Effects from Sophora alopecuroides. Chinese J. Chem. 2021, 39, 3339–3346. [Google Scholar] [CrossRef]
- Yuan, X.; Li, Z.; Feng, Z.; Jiang, J.; Zhang, P. Alopecuroidines A−C, three matrine-derived alkaloids from the seeds of Sophora alopecuroides. Chin. Chem. Lett. 2021, 32, 4058–4062. [Google Scholar] [CrossRef]
- Yuan, X.; Jiang, J.; Yang, Y.; Zhang, X.; Feng, Z.; Zhang, P. Three quinolizidine dimers from the seeds of Sophora alopecuroides and their hepatoprotective activities. Chin. Chem. Lett. 2022, 33, 2923–2927. [Google Scholar] [CrossRef]
- Cheng, X.; Ye, J.; He, H.; Liu, Z.; Xu, C.C.; Wu, B.; Xiong, X.; Shu, X.; Jiang, X.; Qin, X. Synthesis, characterization and in vitro biological evaluation of two matrine derivatives. Sci. Rep. 2018, 8, 15686. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Sun, X.; Zhuo, X.B.; Hu, Y.P.; Zheng, X.; Zhao, Q.J. A novel matrine derivative WM622 inhibits hepatocellular carcinoma by inhibiting PI3K/AKT signaling pathways. Mol. Cell Biochem. 2018, 449, 47–54. [Google Scholar] [CrossRef] [PubMed]
- Hu, H.; Wang, S.; Zhang, C.; Wang, L.; Ding, L.; Zhang, J.; Wu, Q. Synthesis and in vitro inhibitory activity of matrine derivatives towards pro-inflammatory cytokines. Bioorg. Med. Chem. Lett. 2010, 20, 7537–7539. [Google Scholar] [CrossRef]
- Zou, Y.; Sarem, M.; Xiang, S.; Hu, H.; Xu, W.; Shastri, V.P. Autophagy inhibition enhances Matrine derivative MASM induced apoptosis in cancer cells via a mechanism involving reactive oxygen species-mediated PI3K/Akt/mTOR and Erk/p38 signaling. BMC Cancer 2019, 19, 949. [Google Scholar] [CrossRef] [Green Version]
- Xu, W.H.; Hu, H.G.; Tian, Y.; Wang, S.Z.; Li, J.; Li, J.Z.; Deng, X.; Qian, H.; Qiu, L.; Hu, Z.L.; et al. Bioactive compound reveals a novel function for ribosomal protein S5 in hepatic stellate cell activation and hepatic fibrosis. Hepatology 2014, 60, 648–660. [Google Scholar] [CrossRef]
- Zhi, X.; Cui, J.; Liu, C.; Zheng, Z.; Cao, L.; Pan, P.; Weng, W.; Zhai, X.; Zhao, Q.; Hu, H.; et al. A matrine derivative M54 suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by targeting ribosomal protein S5. Front. Pharmacol. 2018, 9, 22. [Google Scholar]
- Chao, L. Aromatic Structure Modification and Bone-Targeting Prodrug Studies of Matrine Derivative M19. Ph.D. Dissertation, Naval Medical University, Shanghai, China, 2020. [Google Scholar]
- Li, L.; Ma, L.; Wang, D.; Jia, H.; Yu, M.; Gu, Y.; Shang, H.; Zou, Z. Design and synthesis of matrine derivatives as novel anti-pulmonary fibrotic agents via repression of the TGFβ/Smad pathway. Molecules 2019, 24, 1108. [Google Scholar] [CrossRef] [Green Version]
- Altieri, D.C. Survivin–The inconvenient IAP. Semin. Cell Dev. 2015, 39, 91–96. [Google Scholar] [CrossRef] [Green Version]
- Yin, H.; Que, R.; Liu, C.; Ji, W.; Sun, B.; Lin, X.; Zhang, Q.; Zhao, X.; Peng, Z.; Zhang, X.; et al. Survivin-targeted drug screening platform identifies a matrine derivative WM-127 as a potential therapeutics against hepatocellular carcinoma. Cancer Lett. 2018, 425, 54–64. [Google Scholar] [CrossRef]
- Wang, L.; You, Y.; Wang, S.; Liu, X.; Liu, B.; Wang, J.; Lin, X.; Chen, M.; Liang, G.; Yang, H. Synthesis, characterization and in vitro anti-tumor activities of matrine derivaives. Bioorg. Med. Chem. Lett. 2012, 22, 4100–4102. [Google Scholar] [CrossRef] [PubMed]
- Xie, M.; Yi, X.; Wang, R.; Wang, L.; He, G.; Zhu, M.; Qi, C.; Liu, Y.; Ye, Y.; Tan, S.; et al. 14-Thienyl methylene matrine (YYJ18), the derivative from matrine, induces apoptosis of human nasopharyngeal carcinoma cells by targeting MAPK and PI3K/Akt pathways in votro. Cell Physiol. Biochem. 2014, 33, 1475–1483. [Google Scholar] [CrossRef]
- Kong, L. Thienyl Methylene Matrine (YYJ18) Inhibits the Proliferation, Migration and Invasion in Nasopharyngenal Carcinoma Cell through mir-146B-5p Pathway. Ph.D. Dissertation, Guangxi Medical University, Nanning, China, 2019. [Google Scholar]
- Wu, L.; Wang, G.; Wei, J.; Huang, N.; Zhang, S.; Yang, F.; Li, M.; Zhou, G.; Wang, L. Matrine derivative YF-18 inhibits lung cancer cell proliferation and migration through down-regulating Skp2. Oncotarget 2017, 8, 11729. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Li, Z.; Luo, M.; Cai, B.; Wu, L.; Huang, M.; Haroon-Ur-Rashid; Jiang, J.; Wang, L. Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents. Bioorg. Med. Chem. Lett. 2018, 28, 677–683. [Google Scholar] [CrossRef]
- Li, Z.; Wu, L.; Cai, B.; Luo, M.; Huang, M.; Rashid, H.U.; Yang, Y.; Jiang, J.; Wang, L. Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents. Med. Chem. Res. 2018, 27, 1941–1955. [Google Scholar] [CrossRef]
- Wei, J.; Liang, Y.; Wu, L. Design, synthesis, molecular docking, and tumor resistance reversal activity evaluation of matrine derivative with thiophene structure. Molecules 2021, 26, 417. [Google Scholar] [CrossRef]
- Jing, D.; Wang, H.; Xu, Y.; Liu, X.; Wan, L. Synthesis and Antitumor Activities of Novel 15-N-Substituted Matrine Imine Derivatives. Chin. J. Syn. Chem. 2019, 27, 6. [Google Scholar]
- Xu, Y.; Liang, P.; Rashid, H.; Wu, L.; Xie, P.; Wang, H.; Zhang, S.; Wang, L.; Jiang, J. Design, synthesis, and biological evaluation of matrine derivatives possessing piperazine moiety as antitumor agents. Med. Chem. Res. 2019, 28, 1618–1627. [Google Scholar] [CrossRef]
- Tang, S.; Li, Y.H.; Cheng, X.Y.; Yin, J.Q.; Li, Y.H.; Song, D.Q.; Wang, Y.X.; Liu, Z.D. Synthesis and biological evaluation of 12n-substituted tricyclic matrinic derivatives as a novel family of anti-influenza agents. Med. Chem. 2018, 14, 764–772. [Google Scholar] [CrossRef]
- Zhang, X.; Liu, Q.; Li, Q.; Li, Y.; Liu, Z.; Deng, H.; Tang, S.; Wang, Y.; Wang, Y.; Song, D. Synthesis and biological evaluation of novel tricyclic matrinic derivatives as potential anti-filovirus agents. Acta Pharm. Sin. B 2018, 8, 629–638. [Google Scholar] [CrossRef] [PubMed]
- Emwas, A.H.; Szczepski, K.; Poulson, B.G.; Chandra, K.; McKay, R.T.; Dhahri, M.; Fatimah, A.; Jaremko, L.; Lachowicz, J.I.; Jaremko, M. NMR as a “gold standard” method in drug design and discovery. Molecules 2020, 25, 4597. [Google Scholar] [CrossRef] [PubMed]
- Emwas, A.H.M.; Al-Rifai, N.; Szczepski, K.; Alsuhaymi, S.; Rayyan, S.; Almahasheer, H.; Jaremko, M.; Brennan, L.; Lachowicz, J.I. You are what you eat: Application of metabolomics approaches to advance nutrition research. Foods 2021, 10, 1249. [Google Scholar] [CrossRef]
- Almulhim, F.; Rossbach, S.; Emwas, A.H.; Kharbatia, N.M.; Jaremko, L.; Jaremko, M.; Duarte, C.M. Metabolomic Study on Tridacna maxima Giant Clams Reveals Metabolic Fingerprint of Environmental Pollutants. Front. Mar. Sci. 2020, 9, 813404. [Google Scholar] [CrossRef]
- Chandra, K.; Al-Harthi, S.; Sukumaran, S.; Almulhim, F.; Emwas, A.H.; Atreya, H.S.; Jaremko, Ł.; Jaremko, M. NMR-based metabolomics with enhanced sensitivity. RSC Adv. 2021, 11, 8694–8700. [Google Scholar] [CrossRef]
- Chandra, K.; Al-Harthi, S.; Almulhim, F.; Emwas, A.H.; Jaremko, Ł.; Jaremko, M. The robust NMR toolbox for metabolomics. Mol. Omics 2021, 17, 719–724. [Google Scholar] [CrossRef]
- Emwas, A.H.; Roy, R.; McKay, R.T.; Tenori, L.; Saccenti, E.; Gowda, G.A.N.; Raftery, D.; Alahmari, F.; Jaremko, L.; Jaremko, M.; et al. NMR Spectroscopy for Metabolomics Research. Metabolites 2019, 9, 123. [Google Scholar] [CrossRef] [Green Version]
Compound | Activity Test | Result | References |
---|---|---|---|
2–9 | Inhibitory activity against HBsAg and HBeAg secretion | Compounds 2, 5, and 6 had higher inhibition rates on HBsAg and HBeAg secretion than matrine | [43] |
10–14 | Anti-inflammatory Activities in LPS (lipopolysaccharide)-Stimulated RAW 264.7 Cells | The amount of IL-6 produced by the cells treated with the compounds 10–13 and matrine was (67.85 ± 0.44)%, (52.87 ± 3.22)%, (73.90 ± 0.34)% (60.08 ± 1.66)% and (65.49 ± 3.64)% of that in the model group; The amount of TNF-α produced by the cells treated with the compound 10–14 and matrine was (96.64 ± 1.27) %, (50.05 ± 6.56)%, (49.59 ± 0.51)%, (70.86 ± 0.31)%, (69.14 ± 2.18)% and (72.48 ± 3.83)% of that in the model group | [44] |
15–19 | Immunosuppression experiments | Only compound 18 has a strong inhibitory activity on the proliferation of concanavalin A-induced T lymphocytes and LPS-induced B cells in vitro, with IC50 values of 3.98 and 3.74 μM, respectively | [45] |
20–22 | The inhibitory activity on NO production of in RAW 264.7 cells activated by LPS | NG-monomethyl-L-arginine, mono-acetate salt was used as positive control with IC50 value of 21.80 μM. Only compound 20 showed good inhibitory effect with IC50 value of 18.26 μM | [46] |
23–27 | Anti-inflammatory Activities in LPS-Stimulated RAW 264.7 Cells | The amount of IL-6 produced by the cells treated with the compounds 23–27 and matrine was (65.21 ± 0.43)%, (65.89 ± 3.12)%, (73.27 ± 0.28)%, (84.82 ± 1.56)%, (89.26 ± 1.56)% and (82.14 ± 5.75)% of that in the blank group; The amount of TNF-α produced by the cells treated with the compounds 23–27 and matrine was (56.82 ± 1.25)%, (85.21 ± 6.21)%, (80.68 ± 0.62)%, (75.86 ± 0.32)%, (66.36 ± 2.24)% and (73.01 ± 1.56)% of that in the model group | [47] |
28–32 | The inhibitory activity on NO production of in RAW 264.7 cells activated by LPS Antitumor activity was tested with Hela, HepG2 and A549 cells; Anti-HIV and anti-influenza virus activities | The IC50 value of 31b was 29.19 μM, and that of matrine was 38.90 μM. The IC50 value of other new compounds was greater than 50 μM All compounds showed no anti-tumor activity (IC50 > 50 μM) Paclitaxel was a positive control (IC50 = 2.54 μM) All compounds showed no anti-HIV and anti-influenza virus activities | [48] |
33–40 | Anti-neuroinflammatory activity in LPS-stimulated BV2 microglia. | All compounds showed anti-neuroinflammatory activity (the medium without LPS were selected as the positive or negative control group) | [49] |
41–44 | Anti-inflammatory Activities in LPS-Stimulated RAW 264.7 Cells | Compounds 43 and 44 can inhibit the release of TNF-α and IL-6 with IC50 value from 35.6 to 45.8 μM; Compounds 41 and 42 showed no activity with IC50 > 50 μM (Dexamethasone as a positive control group with IC50 values of 8.8 ± 1.3 μM and 7.2 ± 0.5 μM for TNF-α and IL-6) | [50] |
45–49 | Anti-inflammatory Activities in LPS-Stimulated RAW 264.7 Cells | The amount of IL-6 produced by the cells treated with the compounds 45–49 and matrine was (41.0 ± 1.3)%, (54.7 ± 1.7)%, (85.6 ± 1.4)%, >100%, (84.0 ± 1.6)%, (70.8 ± 2.3)%, (73.3 ± 1.6)%, (71.9 ± 0.9)% and (81.0 ± 1.8)% of that in the model group; The amount of TNF-α produced by the cells treated with the compound 45–49 was (34.0 ± 2.9)%, (46.8 ± 1.8)%, (74.7 ± 1.7)%, (90.0 ± 1.5)%, (84.3 ± 1.9)%, (71.7 ± 1.4)%, (73.5 ± 1.0)%, (79.3 ± 2.3)% and (64.3 ± 1.9)% of that in the model group (Dexamethasone as a positive control group with IC50 values of 28.8 ± 2.3 μM and 32.2 ± 3.5 μM for TNF-α and IL-6) | [51] |
Cytotoxicity to HepG2, A549, THP-1, and MCF-7 cells | All new compounds showed no obvious cytotoxic activity against those four human cancer cell lines with CC50 value more than 100 μmol/L (the positive control, Adriamycin showed inhibition rates that ranged from 75–95%.) | [51] | |
50–51 | Anti-proliferative activities against A549 cells. | The IC50 value of compound 50 was 20.92 ± 3.03 μM at 24 h, whereas compound 51a had values greater than 40 μM the IC50 values of compound 50 were 12.82 ± 1.39 μM and 7.58 ± 2.47 μM at 48 h and 72 h, respectively | [52] |
50 | The correlation between the anti-proliferative effect and both cell cycle arrest and apoptosis | 50-treated A549 cells had increased percentages of early and late apoptotic cells in a dose-dependent manner | [52] |
52–54 | The hepatoprotective effect against APAP-induced hepatotoxicity in HepG2 cells and a mice model | The viability of HepG2 cells induced by APAP increased from 46.21% to 77.50% after treatment with compound 52; The level of serum Alanine transaminase and aspartate transaminase in model group were 1429.22 ± 82.84 and 1455.47 ± 97.41 U/L, respectively, and in mice administered with compound 52(30mg/kg) were 66.35 ± 11.03 and 169.70 ± 8.67 U/L, respectively | [53] |
Compound | Activity Test | Method | Result | References |
---|---|---|---|---|
66–68 | Antiproliferative activities of compounds 66–68 against human hepatoma Bel-7402 and colorectal carcinoma RKO cells | MTT assay | The survival rates of Bel-7402 cells treated with matrine and compounds 66–68 series were (86.6 ± 2.6)%, (78.3 ± 2.1)%, (71.3 ± 3.8)%, (89.4 ± 2.2)%, (85.2 ± 2.4)%, (91.2 ± 3.4)%, (88.3 ± 2.0)%, (71.5 ± 2.5)%, (72.3 ± 3.2)%, (78.4 ± 3.2)%, (90.1 ± 0.2)%, (79.9 ± 0.2)%, (75.9 ± 1.3)%, (84.3 ± 3.5)%, (78.1 ± 4.1)%, (73.3 ± 2.8)%, (50.4 ± 1.4)%, (48.3 ± 2.5)%, (73.5 ± 2.1)%, (81.2 ± 4.8)%, (78.8 ± 2.2)%, (76.1 ± 2.6)%, (81.1 ± 4.3)%, (50.6 ± 2.5)%, (72.2 ± 5.4)%, (73.3 ± 2.3)%, (62.6 ± 3.4)%, (61.3 ± 0.2)%, respectively; The survival rates of RKO cells treated with matrine and compounds 66–68 series were (84.3 ± 2.5)%, (81.7 ± 2.1)%, (80.2 ± 2.4)%, (83.8 ± 1.2)%, (75.2 ± 2.6)%, (88.0 ± 1.8)%, (88.7 ± 3.1)%, (76.1 ± 2.5)%, (75.7 ± 2.7)%, (79.8 ± 2.2)%, (79.1 ± 4.6)%, (84.1 ± 3.4%), (72.4 ± 3.8)%, (53.4 ± 1.8)%, (43.8 ± 2.5)%, (58.1 ± 3.7)%, (48.3 ± 3.1)%, (51.3 ± 3.3)%, (76.2 ± 2.7)%, (78.1 ± 2.0)%, (82.6 ± 2.4)%, (87.5 ± 4.8)%, (81.5 ± 2.7)%, (55.2 ± 1.3)%, (76.2 ± 2.7)%, (76.7 ± 3.5)%, (75.8 ± 1.2)%, respectively. | [72] |
69–72 | In vitro anti-flu activities against influenza A/Puerto Rico/8/34 (wild H1N1) | Viral cytopathogenic effect assay | The IC50 values of compounds 69–72 series, Ribavirin and Oseltamivir were 10.7, 19.0, 51.4, 94.2, >169.0, 55.1, 115.9, >158.1, 108.2, >620.4, >594.4, >540.5, >539.8, >501.9, 13.0, 5.3 μM | [73] |
73–80 | In vitro anti-EBOV activities of compounds 73–80 in human embryonic kidney (HEK) 293 T cells. | -- | The IC50 values of compounds 73–80 series and Sertraline were 5.07, 2.68, 39.1, 2.90, 78.6, >200, 11.4, 25.4, 88.2, 8.23, 5.29, >200, >200, 30.2, 28.1, 88.2, 26.8, 10.0, >200, >200, >200, 83.3, >200, 83.3, >200, 83.3, 83.3, 1.08 μM | [74] |
76d | Anti-EBOV and anti-MARV activity in vivo of the compound 76d | BALB/c mice | Compound 76d displayed anti-EBOV activity by contributing a 65% reduction, significantly higher than that of sertraline (45%). Compound 76d displayed anti-MARV activity by contributing a 50% reduction, while sertraline displayed no activity at all. | [74] |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Li, J.; Wei, S.; Marabada, D.; Wang, Z.; Huang, Q. Research Progress of Natural Matrine Compounds and Synthetic Matrine Derivatives. Molecules 2023, 28, 5780. https://doi.org/10.3390/molecules28155780
Li J, Wei S, Marabada D, Wang Z, Huang Q. Research Progress of Natural Matrine Compounds and Synthetic Matrine Derivatives. Molecules. 2023; 28(15):5780. https://doi.org/10.3390/molecules28155780
Chicago/Turabian StyleLi, Jinlei, Shijie Wei, Davies Marabada, Zhizhong Wang, and Qing Huang. 2023. "Research Progress of Natural Matrine Compounds and Synthetic Matrine Derivatives" Molecules 28, no. 15: 5780. https://doi.org/10.3390/molecules28155780
APA StyleLi, J., Wei, S., Marabada, D., Wang, Z., & Huang, Q. (2023). Research Progress of Natural Matrine Compounds and Synthetic Matrine Derivatives. Molecules, 28(15), 5780. https://doi.org/10.3390/molecules28155780