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Chemical Structure| 36052-37-6 Chemical Structure| 36052-37-6

Structure of Alpinetin
CAS No.: 36052-37-6

Chemical Structure| 36052-37-6

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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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Product Details of Alpinetin

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

Safety of Alpinetin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

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

Protocol

Bio Calculators
Preparing Stock Solutions 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

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