Structure of Alpinetin
CAS No.: 36052-37-6
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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.
Alpinetin can act as an inhibitor of UCK2 and shows antioxidant, anticancer and antithrombotic properties. Alpinetin is mainly found in ginger plants.
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CAS No. : | 36052-37-6 |
Formula : | C16H14O4 |
M.W : | 270.28 |
SMILES Code : | O=C1C[C@@H](C2=CC=CC=C2)OC3=C1C(OC)=CC(O)=C3 |
MDL No. : | MFCD00238532 |
InChI Key : | QQQCWVDPMPFUGF-ZDUSSCGKSA-N |
Pubchem ID : | 154279 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
EL-4 cells | 1, 3, 10, 30, 100 μM | 24 h | Alpinetin showed little effect on EL-4 cells viability and could activate AhR | Cell Death Dis. 2018 Aug 30;9(9):890. |
CD4+ T cells | 1, 3, 10, 30 μM | 72 h | Alpinetin concentration-dependently promoted Treg differentiation but had slight effect on Th17 differentiation | Cell Death Dis. 2018 Aug 30;9(9):890. |
human bone marrow mesenchymal stem cells (BMSCs) | 10, 20, 40 μM | 7 and 14 days | To evaluate the effect of Alpinetin on osteogenic differentiation of BMSCs. Results showed that Alpinetin dose-dependently enhanced osteogenic differentiation levels in human BMSCs, as indicated by increased alkaline phosphatase (ALP) activity, increased calcium deposition (detected by Alizarin Red S staining), and elevated protein expression levels of Runx2, OCN, and OPN. | Phytother Res. 2023 Jan;37(1):252-270 |
Mouse fibroblasts (mFB) | 0.01 μg/ml, 1 μg/ml, 100 μg/ml | 72 h | To evaluate the cytotoxicity of Alpinetin on mouse fibroblasts. Results showed that Alpinetin slightly increased proliferation of mouse fibroblasts. | Chin Med. 2022 May 31;17(1):63 |
Mouse keratinocytes (mKC) | 0.01 μg/ml, 1 μg/ml, 100 μg/ml | 48 h | To evaluate the cytotoxicity of Alpinetin on mouse keratinocytes. Results showed that Alpinetin slightly increased mouse keratinocytes proliferation at the high dose (100 μg/ml). | Chin Med. 2022 May 31;17(1):63 |
Human fibroblasts (hFB) | 0.01 μg/ml, 1 μg/ml, 100 μg/ml | 72 h | To evaluate the cytotoxicity of Alpinetin on human fibroblasts. Results showed that Alpinetin at the high dose (100 μg/ml) increased proliferation of human fibroblasts. | Chin Med. 2022 May 31;17(1):63 |
Human keratinocytes (hKC) | 0.01 μg/ml, 1 μg/ml, 100 μg/ml | 48 h | To evaluate the cytotoxicity of Alpinetin on human keratinocytes. Results showed that Alpinetin did not affect cell viability in human keratinocytes at all concentrations. | Chin Med. 2022 May 31;17(1):63 |
Human primary dermal fibroblasts (HPDFs) | 50 µM | 24h, 48h, 72h | Alpinetin inhibits TGF-β1-induced proliferation and migration of HPDFs and inhibits TGF-β1-induced morphological changes of fibroblasts to myofibroblasts. | Cells. 2022 Sep 1;11(17):2731 |
THP-1 macrophages | 1.56-12.5 μM | 48 h | Inhibited ZIKV-induced IL-1β secretion without cytotoxicity | Pharmaceutics. 2022 Dec 14;14(12):2800 |
Human pulmonary microvascular endothelial cells (HPMVEC) | 0.01, 0.1, 1.0, and 10.0 μg/mL | 24, 48, and 72 h | To evaluate the effect of Alpinetin on LPS-induced HPMVEC proliferation. Results showed that Alpinetin promoted HPMVEC proliferation in a time- and dose-dependent manner within the range of 0.01 to 1.0 μg/mL. | Drug Des Devel Ther. 2016 Feb 24;10:841-50 |
AsPC-1 cells | 20, 40, 60, 80 µg/ml | 24, 48, 72 h | Alpinetin inhibited the growth of AsPC-1 cells in a dose- and time-dependent manner. | Int J Mol Med. 2012 Apr;29(4):607-12 |
PANC-1 cells | 20, 40, 60, 80 µg/ml | 24, 48, 72 h | Alpinetin inhibited the growth of PANC-1 cells in a dose- and time-dependent manner. | Int J Mol Med. 2012 Apr;29(4):607-12 |
BxPC-3 cells | 20, 40, 60, 80 µg/ml | 24, 48, 72 h | Alpinetin inhibited the growth and induced apoptosis of BxPC-3 cells in a dose- and time-dependent manner, accompanied by regulation of Bcl-2, Bcl-xL, Bax, and XIAP expression. | Int J Mol Med. 2012 Apr;29(4):607-12 |
A549/CDDP cells | 50-400μM | 24 h, 48 h, 72 h | Alpinetin did not show direct growth-inhibitory effects on A549/CDDP cells but reversed their resistance to CDDP. | Drug Des Devel Ther. 2015 Nov 16;9:6119-27 |
NCI-H292 cells | 50-400μM | 24 h, 48 h, 72 h | Alpinetin inhibited the proliferation of NCI-H292 cells in a dose- and time-dependent manner, with significant effects observed at 72 hours and 200 μM concentration. | Drug Des Devel Ther. 2015 Nov 16;9:6119-27 |
SK-MES-1 cells | 50-400μM | 24 h, 48 h, 72 h | Alpinetin inhibited the proliferation of SK-MES-1 cells in a dose- and time-dependent manner, with significant effects observed at 72 hours and 200 μM concentration. | Drug Des Devel Ther. 2015 Nov 16;9:6119-27 |
A549 cells | 50-400μM | 24 h, 48 h, 72 h | Alpinetin inhibited the proliferation of A549 cells in a dose- and time-dependent manner, with significant effects observed at 72 hours and 200 μM concentration. | Drug Des Devel Ther. 2015 Nov 16;9:6119-27 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Female C57BL/6 mice | DSS-induced colitis | Oral administration | 7.5, 15, 30 mg/kg | Daily for 10 consecutive days | Alpinetin significantly alleviated colitis symptoms in mice and restored Th17/Treg balance | Cell Death Dis. 2018 Aug 30;9(9):890. |
C57BL/6 mice | Glucocorticoid-induced osteoporosis (GIOP) model | Oral | 40 mg/kg | Once daily for 8 weeks | To evaluate the protective effect of Alpinetin on osteoporosis in GIOP mice. Results showed that oral administration of Alpinetin significantly alleviated bone loss in GIOP mice, as indicated by increased bone volume/total volume (BV/TV), trabecular number and thickness, and decreased trabecular spacing. Additionally, Alpinetin promoted osteogenic differentiation of BMSCs by enhancing PKA signaling and autophagy. | Phytother Res. 2023 Jan;37(1):252-270 |
C57BL/6J mice | Depilation model | Topical application | 3 mg/ml | Once daily until sample harvesting | To evaluate the promoting effect of Alpinetin on hair regeneration. Results showed that topical application of AP promoted anagen initiation and delayed catagen entry, resulting in a longer anagen phase and hair shaft length. Mechanistically, AP activated Lgr5+ hair follicle stem cells (HFSCs) via Wnt signaling and promoted the proliferation of other HFSCs (including K15+, Lef1+, and Gli1+ cells). Additionally, AP inhibited cleaved caspase 3-dependent apoptosis at the late anagen stage to postpone regression of hair follicles. | Chin Med. 2022 May 31;17(1):63 |
C57BL/6 mice | Lieber–DeCarli ethanol liquid diet-induced alcoholic liver disease model | Oral gavage | 10 mg/kg | Once daily for the last five days of the experimental period | Alpinetin significantly reduced serum levels of ALT, AST, γ-GT, and oxidative/nitrosative stress markers while increasing antioxidative markers. The levels of pro-inflammatory cytokines and ER stress parameters were significantly decreased. Histological analysis demonstrated reduced steatosis, hepatocyte ballooning, and inflammation. | Int J Mol Sci. 2024 Dec 26;26(1):86 |
Adult male Sprague Dawley rats | Severe acute pancreatitis (SAP)-induced acute lung injury (ALI) model | Intragastric administration | 40, 80, 160, and 320 μg/mL | Rats were sacrificed at 6, 12, and 24 hours after model construction | To investigate the therapeutic effect of Alpinetin on SAP-induced ALI. Results showed that 160 μg/mL Alpinetin significantly improved lung tissue pathology and lung wet-to-dry weight ratio (W/D), with no significant difference compared to the dexamethasone group. | Drug Des Devel Ther. 2016 Feb 24;10:841-50 |
Nude mice | A549/CDDP xenograft model | Subcutaneous injection | 50 mg/kg | Once weekly for 4 weeks | Alpinetin significantly inhibited the growth of xenograft tumors and sensitized drug-resistant lung cancer cells to the chemotherapeutic effects of CDDP. | Drug Des Devel Ther. 2015 Nov 16;9:6119-27 |
Bio Calculators | ||||
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1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
3.70mL 0.74mL 0.37mL |
18.50mL 3.70mL 1.85mL |
37.00mL 7.40mL 3.70mL |
Tags: Alpinetin | PPAR | Peroxisome proliferator-activated receptors | inhibitor | 36052-37-6 |
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