Structure of Paeonol
CAS No.: 552-41-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Paeonol is a naturally occuring MAO inhibitor with IC50 values of 54.6 μM and 42.5 μM for MAO-A and MAO-B, respectively.
Synonyms: 2'-Hydroxy-4'-methoxyacetophenone; Peonol; NSC 401442
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Han, Guanqun ;
Abstract: Mankind's sustainable development not only requires the capture and conversion of renewable energies but also necessitates the production of chemical goods from renewable carbon sources. Biomass is the only accessible and renewable carbon source. One major class of biomass is degradative small molecules, among which 5-hydroxymethylfurfural (HMF) is considered as a platform chemical and it can serve as a starting material to produce various upgrading compounds, eg, the oxidation products, 2, 5-furan dicarboxylic acid (FDCA), and 2, 5-diformylfuran (DFF), can act as biopolymer precursors. In this dissertation, we successfully demonstrated that ultrathin Ni/CdS nanosheets can be efficient photocatalyst to produce value-added bioproducts (eg, furoic acid, DFF, and FDCA) from biomass-derived molecules. Even more desirable is that the oxidative biomass upgrading can be integrated with H2 production.
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| CAS No. : | 552-41-0 |
| Formula : | C9H10O3 |
| M.W : | 166.17 |
| SMILES Code : | CC(C1=CC=C(OC)C=C1O)=O |
| Synonyms : |
2'-Hydroxy-4'-methoxyacetophenone; Peonol; NSC 401442
|
| MDL No. : | MFCD00008730 |
| InChI Key : | UILPJVPSNHJFIK-UHFFFAOYSA-N |
| Pubchem ID : | 11092 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302+H312+H332-H315-H319-H335-H412 |
| Precautionary Statements: | P261-P273-P280-P305+P351+P338 |
| Target |
|
In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| HCT116 cells | 7.8125, 15.625, 31.25, 62.5, 125, 250 and 500 µg/ml | 12, 24, 48 and 72 hours | To assess the inhibitory effect of Paeonol on HCT116 cell viability, the results showed that Paeonol significantly inhibited the proliferation of HCT116 cells in a dose- and time-dependent manner. | Int J Mol Med. 2020 Aug;46(2):675-684. |
| SKOV3 cells | 1.2 mM | 24 and 48 hours | To evaluate the inhibitory effect of Paeonol on cell proliferation, results showed that Paeonol significantly inhibited the proliferation of SKOV3 cells. | Cell Death Dis. 2019 Aug 13;10(8):609. |
| A2780 cells | 1.2 mM | 24 and 48 hours | To evaluate the inhibitory effect of Paeonol on cell proliferation, results showed that Paeonol significantly inhibited the proliferation of A2780 cells. | Cell Death Dis. 2019 Aug 13;10(8):609. |
| NSC-34/hSOD1G93A (MT) | 100 µM | 24 hours | Evaluate the protective effect of Paeonol against glutamate, LPS, and H2O2-induced cytotoxicity, results showed Paeonol significantly improved cell viability | Antioxidants (Basel). 2022 Jul 18;11(7):1392. |
| NSC-34/hSOD1WT (WT) | 100 µM | 24 hours | Evaluate the protective effect of Paeonol against glutamate, LPS, and H2O2-induced cytotoxicity, results showed Paeonol significantly improved cell viability | Antioxidants (Basel). 2022 Jul 18;11(7):1392. |
| Cardiomyocytes | 50 µM | 24 hours | Paeonol promotes Mfn2-mediated mitochondrial fusion, restores mitochondrial function and cell viability, and inhibits Dox-induced cardiomyocyte apoptosis and oxidative stress. | J Adv Res. 2023 May;47:151-162. |
| Primary microglial cells | 0.5 to 1 mM | 24 hours | Paeonol inhibited lipopolysaccharide-induced nitrite release and reduced the secretion of tumor necrosis factor-alpha and interleukin-1β. | Neural Regen Res. 2013 Jun 25;8(18):1637-43. |
| RAW 264.7 cells | 25, 50 µM | 24 hours | Evaluate the effect of paeonol on LPS-induced MAPK protein expression in RAW 264.7 cells. Results showed that paeonol significantly reduced the protein expression levels of COX-2 and NF-κB and affected the phosphorylation of p-p38. | Biomolecules. 2022 Nov 3;12(11):1634. |
| RAW 264.7 cells | 6.3, 12.5, 25, 50 µM | 24 hours | Evaluate the effect of paeonol on LPS-induced IL-6 and TNF-α production in RAW 264.7 cells. Results showed that paeonol inhibited the release of IL-6 and TNF-α in a concentration-dependent manner. | Biomolecules. 2022 Nov 3;12(11):1634. |
| GMI-R1 cells | 4 µM | 24 hours | Paeonol promotes the transformation of LPS-treated GMI-R1 microglia from the M1 phenotype to the M2 phenotype. | CNS Neurosci Ther. 2023 Sep;29(9):2666-2679. |
| Human primary umbilical vein endothelial cell (HUVEC) | 10 µM | 24 hours | To evaluate the effect of Paeonol on HUVEC cell viability, results showed that Paeonol treatment significantly enhanced HUVEC viability. | Drug Des Devel Ther. 2023 May 24;17:1567-1582. |
| Aspergillus flavus | 0.625 mg/mL | 24 hours | Paeonol significantly destroyed both the outer amorphous layer and the inner fibrous layer of A. flavus cell walls, leading to thinner cell walls and chaotic cytoplasm. | Foods. 2021 Dec 1;10(12):2951. |
| Human umbilical vein/vascular endothelial cell line (HUVEC-C) | 10 µM | 24 hours, 48 hours, 72 hours | To evaluate the effect of Paeonol on HUVEC-C cell numbers, results showed that Paeonol treatment significantly increased cell numbers. | Drug Des Devel Ther. 2023 May 24;17:1567-1582. |
| RAW264.7 macrophages | 32, 64, 128 µg/mL | 3 hours pretreatment or 4 hours treatment | To assess the anti-infection activity and mechanism of paeonol against P. aeruginosa infection in vitro, results showed paeonol downregulated the expression of QS-related virulence genes and reduced PAO1-induced cell damage | Front Immunol. 2022 May 24;13:896874. |
| BV-2 microglial cells | 10 or 30 µM | 30 min pretreatment followed by 24 hours stimulation | To investigate the effects of Paeonol on ATP-induced cell migratory activity. Results showed that Paeonol effectively reduced ATP-enhanced migratory activity. | Int J Mol Sci. 2015 Apr 21;16(4):8844-60. |
| BV-2 microglial cells | 3, 10, or 30 µM | 30 min pretreatment followed by 24 hours stimulation | To investigate the inhibitory effects of Paeonol on LPS/IFN-γ-induced inflammatory responses. Results showed that Paeonol significantly inhibited the release of NO and the expressions of iNOS and COX-2. | Int J Mol Sci. 2015 Apr 21;16(4):8844-60. |
| Primary cardiomyocytes | 25, 50, 100, 200 µM | 48 hours | To evaluate the effects of Paeonol on mitochondrial fusion and function in high glucose-treated cardiomyocytes. Results showed that 100 μmol/L Paeonol significantly increased mitochondrial volume, decreased mitochondrial number, inhibited mitochondrial oxidative stress, and improved ATP production and mitochondrial respiratory capacity. | Redox Biol. 2021 Oct;46:102098. |
| SW1353 cells | 3, 10, 30 µM | 48 hours | Evaluate the effect of Paeonol on the viability of SW1353 cells, showing no effect on cell viability at 3–30 μM | Int J Mol Sci. 2014 Jul 2;15(7):11760-72. |
| JJ012 cells | 3, 10, 30 µM | 48 hours | Evaluate the effect of Paeonol on the viability of JJ012 cells, showing no effect on cell viability at 3–30 μM | Int J Mol Sci. 2014 Jul 2;15(7):11760-72. |
| NSC-34/hSOD1G93A (MT) | 347 nM | 5 min | Evaluate the uptake characteristics of [3H]Paeonol, results showed time-, concentration-, and pH-dependent uptake | Antioxidants (Basel). 2022 Jul 18;11(7):1392. |
| NSC-34/hSOD1WT (WT) | 347 nM | 5 min | Evaluate the uptake characteristics of [3H]Paeonol, results showed time-, concentration-, and pH-dependent uptake | Antioxidants (Basel). 2022 Jul 18;11(7):1392. |
| RAW 264.7 cells | 6.3, 12.5, 25, 50 µM | 6 hours | Evaluate the effect of paeonol on LPS-induced mRNA expression of IL-6, IL-1β, and TNF-α in RAW 264.7 cells. Results showed that paeonol reduced the mRNA expression levels of these inflammatory cytokines in a concentration-dependent manner. | Biomolecules. 2022 Nov 3;12(11):1634. |
| Organotypic hippocampal slice cultures | 0.5 and 1 mM | 72 hours | Paeonol pretreatment markedly blocked lipopolysaccharide-induced hippocampal cell death and inhibited the release of nitrite and interleukin-1beta. | Neural Regen Res. 2013 Jun 25;8(18):1637-43. |
| 3T3-L1 cells | 1000 µM | 8 days | Paeonol inhibits the differentiation of 3T3-L1 cells into mature adipocytes and reduces lipid accumulation. | Nutrients. 2020 Jan 24;12(2):309. |
In Vivo:
|
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
| ICR mice | LPS-induced neuroinflammation model | Intraperitoneal injection | 10 or 30 mg/kg | Once daily for three consecutive days, followed by a single LPS injection | To investigate the effects of Paeonol on LPS-induced motor coordination dysfunction and microglial activation. Results showed that Paeonol significantly improved motor coordination in LPS-injected mice and reduced microglial activation. | Int J Mol Sci. 2015 Apr 21;16(4):8844-60. |
| Sprague-Dawley rats | Chronic constrictive injury (CCI) model | Intragastric administration | 100 mg/kg | Twice daily for 21 days | Paeonol alleviates neuropathic pain by modulating microglial M1 and M2 polarization via the RhoA/p38MAPK signaling pathway. | CNS Neurosci Ther. 2023 Sep;29(9):2666-2679. |
| Wistar rats | Hepatic ischemia/reperfusion injury model | Oral | 100 mg/kg | Once daily for 7 days | To evaluate the protective effect of paeonol against hepatic ischemia/reperfusion injury, results showed that paeonol attenuated liver injury by inhibiting oxidative stress, inflammation, and apoptosis. | Antioxidants (Basel). 2022 Aug 29;11(9):1687 |
| Sprague-Dawley rats | Dox-induced cardiotoxicity model | Oral gavage | 150 mg/kg | Once daily for two weeks | Paeonol activates the PKCε-Stat3-Mfn2 signaling pathway to promote mitochondrial fusion, alleviating Dox-induced cardiotoxicity and myocardial injury. | J Adv Res. 2023 May;47:151-162. |
| BALB/c mice | IMQ-induced psoriasis-like skin inflammation model | Oral | 20 mg/kg and 40 mg/kg | Once daily for 7 days | To evaluate the therapeutic effect of compound B12 on IMQ-induced psoriasis-like skin inflammation. Results showed that compound B12 significantly alleviated skin inflammation symptoms and PASI score. | J Orthop Translat. 2024 Nov 24;50:1-13 |
| BALB/c mice | IMQ-induced psoriasis-like skin inflammation model | Oral | 20 mg/kg and 40 mg/kg | Once daily for 7 days | To evaluate the therapeutic effect of compound B12 on IMQ-induced psoriasis-like skin inflammation. Results showed that compound B12 significantly alleviated skin inflammation symptoms and PASI score. | J Enzyme Inhib Med Chem. 2022 Dec;37(1):817-831 |
| SPF mice | PAO1 acute infection model | Intragastric administration | 25, 50, 100 mg/kg | 3 consecutive days | To evaluate the anti-infection activity of paeonol in vivo, results showed paeonol decreased the bacterial load in the lung and inhibited the mRNA expression of inflammation cytokines | Front Immunol. 2022 May 24;13:896874. |
| BALB/c mice | Lincomycin-induced antibiotic-associated diarrhea model | Oral | 25, 50, 100 mg/kg | Twice daily for 7 days | Evaluate the effect of paeonol on lincomycin-induced diarrhea in mice. Results showed that paeonol significantly improved diarrhea symptoms, reduced weight loss and water intake, and decreased serum levels of TNF-α and IL-4. | Biomolecules. 2022 Nov 3;12(11):1634. |
| ApoE−/− mice | Murine carotid artery catheter guide wires injury model | Intraperitoneal injection | 30 mg/kg | Pretreated for 7 consecutive days, continued treatment after surgery until tissue collection | To evaluate the effect of Paeonol on vascular stenosis after vascular injury, results showed that Paeonol treatment significantly suppressed vascular neointima formation. | Drug Des Devel Ther. 2023 May 24;17:1567-1582. |
| BALB/c nude mice | A2780 xenograft model | Intraperitoneal injection | 40 mg/kg | Once every 2 days, total of 6 times (12 days) | To evaluate the antitumor activity of Paeonol in vivo, results showed that Paeonol significantly inhibited tumor growth, and the effect was enhanced when combined with the autophagy inhibitor HCQ. | Cell Death Dis. 2019 Aug 13;10(8):609. |
| Sprague-Dawley rats | Diabetic cardiomyopathy model | Oral gavage | 75, 150, 300 mg/kg | Once daily for 12 weeks | To evaluate the protective effects of Paeonol on diabetic cardiomyopathy. Results showed that Paeonol (150 or 300 mg/kg/day) significantly improved cardiac function, reduced myocardial hypertrophy and fibrosis, inhibited cardiomyocyte apoptosis and oxidative stress, and promoted mitochondrial fusion and functional recovery. | Redox Biol. 2021 Oct;46:102098. |
Tags: Paeonol | Monoamine Oxidase | Autophagy | MAO | autophagy inducer | Paeonia suffruticosa | antioxidant properties | neuroprotective | anti-inflammatory | cellular recycling | autophagic pathway | damaged protein removal | 552-41-0
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| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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