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Chemical Structure| 2306-27-6 Chemical Structure| 2306-27-6

Structure of Sinensetin
CAS No.: 2306-27-6

Chemical Structure| 2306-27-6

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Sinensetin is a methylated flavone isolated and purified from the fruit of Citrus aurantium L. with antimutagenic, anticancer, and anti-inflammatory activities.

Synonyms: Pedalitin permethyl ether

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Product Details of Sinensetin

CAS No. :2306-27-6
Formula : C20H20O7
M.W : 372.37
SMILES Code : COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O1
Synonyms :
Pedalitin permethyl ether
MDL No. :MFCD00017421
InChI Key :LKMNXYDUQXAUCZ-UHFFFAOYSA-N
Pubchem ID :145659

Safety of Sinensetin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P302+P352-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Mouse chondrocytes 40 µM 0, 6, 12, 24, 48 hours Evaluate the effect of 40 μM Sinensetin on chondrocyte autophagy at different time points. Results showed autophagy marker expression peaked at 24 hours. Front Pharmacol. 2021 Jul 16;12:713491
Periodontal ligament cells (PDLCs) 2.5, 5, 10 µM 24 hours To evaluate the effect of Sin on oxidative stress and inflammatory levels. Results showed that Sin significantly attenuated TNF-α and IL-1β-induced oxidative stress, decreased MDA and ROS levels, increased GSH content, reduced IL6 mRNA expression, and upregulated IL10 mRNA expression. Int J Oral Sci. 2024 May 11;16(1):38
Mouse chondrocytes 40 µM 24 hours Evaluate the effect of Sinensetin on the AMPK/mTOR signaling pathway. Results showed Sinensetin increased p-AMPK expression and decreased p-mTOR expression. Front Pharmacol. 2021 Jul 16;12:713491
Mouse chondrocytes 0, 10, 20, 30, 40 µM 24 hours Evaluate the effect of Sinensetin on chondrocyte autophagy. Results showed Sinensetin increased Beclin1 and LC3II/LC3I ratio and decreased p62 expression. Front Pharmacol. 2021 Jul 16;12:713491
Mouse chondrocytes 40 µM 24 hours Evaluate the effect of Sinensetin on TBHP-induced ECM degradation. Results showed Sinensetin increased aggrecan and collagen II expression and decreased MMP13 expression. Front Pharmacol. 2021 Jul 16;12:713491
Mouse chondrocytes 40 µM 24 hours Evaluate the protective effect of Sinensetin on TBHP-induced chondrocyte apoptosis. Results showed Sinensetin reduced TUNEL-positive cells, downregulated cleaved caspase 3 and Bax expression, and upregulated Bcl-2 expression. Front Pharmacol. 2021 Jul 16;12:713491
HEK293 cells 0-120 μg/mL 24 hours To evaluate the inhibitory effect of Sinensetin on NF-κB transcriptional activity, results showed that Sinensetin inhibited TNF-α or influenza H1N1 virus-stimulated NF-κB activation. BMC Complement Med Ther. 2020 May 5;20(1):135
A549 cells 0-120 μg/mL 24 hours To evaluate the inhibitory effect of Sinensetin on influenza A virus-induced inflammatory response, results showed that Sinensetin significantly reduced the expression of IL-6, TNF-α, IP-10, IL-8, and MCP-1. BMC Complement Med Ther. 2020 May 5;20(1):135
Thle2 cells 25, 50, 75, 100 µM 24 hours or 48 hours To evaluate the effect of Sinensetin on Thle2 cell viability, results showed that Sinensetin had minimal effect on Thle2 cell proliferation Nutrients. 2020 Aug 15;12(8):2462
HepG2 cells 25, 50, 75, 100 µM 24 hours or 48 hours To evaluate the effect of Sinensetin on HepG2 cell viability, results showed that Sinensetin significantly inhibited HepG2 cell proliferation Nutrients. 2020 Aug 15;12(8):2462
Hep3B cells 25, 50, 75, 100 µM 48 hours To evaluate the effect of Sinensetin on Hep3B cell viability, results showed that Sinensetin induced apoptosis in Hep3B cells Nutrients. 2020 Aug 15;12(8):2462
RAW264.7 cells 12.5 µM, 25 µM, 50 µM 6 hours (mRNA level detection) or 24 hours (protein level detection) To investigate the effect of Sinensetin on LPS-induced inflammatory response. Results showed that high-dose Sinensetin significantly inhibited the expression of M1-type macrophage polarization markers (iNOS, COX2, and CD86), promoted the expression of M2-type macrophage markers (Cd206, Cd68, and Agr1), and reduced the expression of pro-inflammatory cytokines TNFα and IL6 while increasing the expression of anti-inflammatory cytokine IL-10. ACS Omega. 2023 Sep 7;8(37):33514-33525

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
ICR/CD-1 mice Hepatic ischemia-reperfusion injury (HIRI) model Intraperitoneal injection 25 mg/kg and 50 mg/kg Once daily for 7 days Sinensetin pretreatment significantly alleviated liver injury in the HIRI model, as evidenced by significant reductions in ALT, AST, and LDH enzyme activities, marked improvements in hepatocyte necrosis and lipid deposition, and a concentration-dependent decrease in the expression of inflammation-related genes. Additionally, Sinensetin significantly reduced liver apoptosis and the expression of apoptosis-related genes (such as BAX and Bcl-2) and modulated key genes in the endoplasmic reticulum stress signaling pathway (such as GRP78 and CHOP). Front Pharmacol. 2025 Feb 12;16:1519497
SD rats Ligation-induced periodontitis model Oral gavage 5, 10, 20 mg/kg Once daily for three weeks To evaluate the protective effect of Sin against periodontitis. Results showed that Sin significantly reduced alveolar bone resorption, decreased inflammatory cell numbers and inflammatory cytokine levels (TNF-α, IL-1β, IL-6), inhibited Bach1 levels, and increased the expression of the antioxidant factor HO-1. Int J Oral Sci. 2024 May 11;16(1):38
C57BL/6 male mice Destabilization of the medial meniscus (DMM) model Oral gavage 50 mg/kg/day Once daily for 8 weeks Evaluate the protective effect of Sinensetin on DMM-induced OA. Results showed Sinensetin improved joint space narrowing and cartilage calcification, reduced MMP13 expression, and increased LC3 expression. Front Pharmacol. 2021 Jul 16;12:713491
C57BL/6J male mice Bleomycin-induced pulmonary fibrosis model Intragastric administration 50, 100, 200 mg/kg/day Once daily for 28 days To study the therapeutic effect of Sinensetin on pulmonary fibrosis, the results showed that Sinensetin significantly alleviated the pathological changes of pulmonary fibrosis, reduced collagen deposition and inflammatory response Front Pharmacol. 2021 Jun 18;12:693061
C57BL/6 male mice LPS-induced inflammatory injury model Intraperitoneal injection Low dose at 12.5 mg/kg/day, medium dose at 25 mg/kg/day, high dose at 50 mg/kg/day Once daily for 4 days To investigate the protective effect of Sinensetin on LPS-induced inflammatory injury. Results showed that high-dose Sinensetin significantly reduced the liver/body weight ratio, decreased serum ALT and AST levels, alleviated inflammatory infiltration and injury in the lungs and liver, and reduced serum TNFα, IL6, and IL1β levels. ACS Omega. 2023 Sep 7;8(37):33514-33525

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.69mL

0.54mL

0.27mL

13.43mL

2.69mL

1.34mL

26.86mL

5.37mL

2.69mL

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