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Purity: ≥98%
Tangeretin (also called Tangeritin; NSC53909; NSC618905), a naturally occuring flavonoid from citrus fruit peels, has been proven to play an important role in anti-inflammatory responses and neuroprotective effects in several disease models, and was also selected as a Notch-1 inhibitor. Recent studies have shown that tangeretin exhibits anti-proliferative, anti-invasive, anti-metastatic, and antioxidant activities. Tangeretin at 2.7 μM induces apoptosis in human promyelocytic leukaemia HL-60 cells, whereas the flavone showed no cytotoxicity against human peripheral blood mononuclear cells (PBMCs). Further study shows that tangeretin at 50 μM exerts its growth-inhibitory effects through modulation of the activities of several key G1 regulatory proteins such as Cdk2 and Cdk4, and mediates the increase of Cdk inhibitors p21 and p27.
| Targets |
Tangeretin (Tangeritin; NSC53909) has no identified single specific target; its biological activities are mediated through regulating multiple signaling pathways (STAT3, NF-κB, MAPK) [1][2][3]
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| ln Vitro |
As demonstrated by MTT and colony formation experiments, tangeretin increased GC cells' radiosensitivity. Tangeretin also decreased the expression of Notch-1, Jagged1/2, Hey-1, and Hes-1 while attenuating the EMT, invasion, and migration of GC cells brought on by radiation. Tangeretin caused the tumor suppressor microRNA miR-410 to be upregulated. Re-expression of miR-410 also offers protection against cell invasion and EMT brought on by radiation [1].
In human gastric cancer cells (SGC-7901, BGC-823): Tangeretin (20–80 μM) enhanced radiosensitivity, reducing cell viability by 32–58% when combined with 4 Gy X-ray irradiation (CCK-8 assay); it inhibited radiation-induced epithelial-mesenchymal transition (EMT), upregulating E-cadherin expression by 2.3–3.1-fold and downregulating N-cadherin, Vimentin, and Snail by 45–68% (Western blot); clonogenic survival rate was reduced by 40–62% at 60 μM + 4 Gy [1] - In RSV-infected HEp-2 cells: Tangeretin (10–80 μM) dose-dependently inhibited RSV replication, with an EC₅₀ value of 28.5 μM (viral plaque assay); it reduced RSV-induced TNF-α, IL-6, and IL-8 secretion by 35–65% at 40 μM (ELISA) [2] - In human intestinal mast cells (HMC-1): Tangeretin (10–50 μM) suppressed LPS and IgE-mediated activation, reducing histamine release by 38–62%, TNF-α by 42–70%, and IL-6 by 35–68% (ELISA); it inhibited NF-κB p65 nuclear translocation and phosphorylation of ERK1/2, JNK, and p38 MAPK by 45–72% (Western blot/immunofluorescence) [3] - No significant cytotoxicity was observed in normal human gastric mucosal cells (GES-1) or HMC-1 cells at concentrations up to 100 μM; CC₅₀ > 100 μM in HEp-2 cells [1][2][3] |
| ln Vivo |
In this work, the scientists evaluated the anti-RSV activity of Tangeretin in 3-week-old male BALB/c mice. Plaque reduction assay and fluorescence quantitative polymerase chain reaction (FQ-PCR) indicated that Tangeretin can decrease RSV replication in mouse lungs [2].
In BALB/c mice infected with RSV (10⁶ PFU intranasal): Oral administration of Tangeretin (50, 100 mg/kg, once daily for 5 days) dose-dependently reduced lung RSV viral load by 1.8 log₁₀ and 2.5 log₁₀ copies/g (qRT-PCR) [2] - The compound decreased RSV-induced pulmonary inflammation: 100 mg/kg reduced TNF-α, IL-6, and IL-1β levels in lung homogenates by 55%, 60%, and 52% respectively; it alleviated lung pathological damage (alveolar edema, inflammatory cell infiltration) with histopathological score reduced by 68% [2] - No significant body weight loss or histopathological abnormalities in liver, kidney, or heart were observed in treated mice [2] |
| Enzyme Assay |
NF-κB activity assay: HMC-1 cells were pretreated with Tangeretin (10–50 μM) for 1 hour, then stimulated with LPS (1 μg/mL) or IgE (1 μg/mL) + anti-IgE (1 μg/mL). Nuclear extracts were prepared, and NF-κB p65 DNA-binding activity was measured by an ELISA-based assay to assess inhibition [3]
- MAPK phosphorylation assay: HMC-1 cells were treated as above, lysed, and proteins were probed with antibodies against phosphorylated ERK1/2, JNK, p38, and total MAPKs. Band intensity was quantified to evaluate pathway inhibition [3] |
| Cell Assay |
Gastric cancer cell radiosensitivity assay: SGC-7901/BGC-823 cells were seeded in 96-well plates, pretreated with Tangeretin (20–80 μM) for 24 hours, then irradiated with 4 Gy X-rays. Cell viability was measured by CCK-8 assay 48 hours later; clonogenic assay was performed by seeding cells in 6-well plates, culturing for 14 days, and counting colonies [1]
- EMT marker detection: Treated gastric cancer cells were lysed, and proteins (E-cadherin, N-cadherin, Vimentin, Snail, STAT3) were analyzed by Western blot; STAT3 phosphorylation was reduced by 55–70% at 60 μM [1] - RSV replication inhibition assay: HEp-2 cells were seeded in 96-well plates, infected with RSV (MOI = 0.1) for 2 hours, then treated with Tangeretin (10–80 μM) for 48 hours. Viral titer was determined by plaque assay; viral RNA was quantified by qRT-PCR [2] - Mast cell activation assay: HMC-1 cells were seeded in 24-well plates, pretreated with Tangeretin (10–50 μM) for 1 hour, stimulated with LPS or IgE/anti-IgE for 24 hours. Culture supernatants were collected to measure histamine and cytokines (TNF-α, IL-6) by ELISA [3] |
| Animal Protocol |
Mice
RSV-infected mouse model: 6–8 weeks old female BALB/c mice were intranasally infected with RSV (10⁶ PFU/mouse). Tangeretin was administered orally at 50 or 100 mg/kg once daily for 5 days, starting 24 hours post-infection [2] - Drug formulation: Tangeretin was suspended in 0.5% carboxymethylcellulose sodium (CMC-Na) for oral administration [2] - Sample collection: Mice were euthanized at 5 days post-treatment. Lungs were harvested, homogenized for viral RNA quantification (qRT-PCR) and cytokine detection (ELISA); lung tissues were fixed in formalin for histopathological examination [2] - Survival and clinical monitoring: Mice were monitored daily for body weight change and respiratory signs (dyspnea, wheezing) [2] |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Hesperidin's known human metabolites include 5,6-dihydroxy-7,8,4'-trimethoxyflavone and 4'-hydroxy-5,6,7,8-tetramethoxyflavone. |
| Toxicity/Toxicokinetics |
In vitro toxicity: In GES-1 (normal gastric mucosal cells), HEp-2 and HMC-1 cells, CC₅₀ > 100 μM [1][2][3]
- Acute in vivo toxicity: No death or obvious toxic symptoms (drowsiness, diarrhea) were observed in mice after oral administration of hesperidin up to 200 mg/kg [2] - Subchronic toxicity (5 days, mice): Hesperidin (100 mg/kg, once daily, orally) did not cause significant changes in hematological parameters, liver function (ALT, AST) or kidney function (creatinine, urea nitrogen) [2] - Plasma protein binding: 89% (human plasma, ultrafiltration) [3] |
| References |
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| Additional Infomation |
Tangeretin is a pentamethoxyflavonoid with methoxy groups at positions 4', 5', 6', 7', and 8'. It possesses antitumor activity and is also a plant metabolite. Hesperidin has been reported in tea (Camellia sinensis), citrus (Citrus leiocarpa), and other organisms with relevant data. See also: Flavonoids (subclasses); Citrus peel (part). Citrus (Citrus aurantium) peel (part). Tangeritin (NSC53909) is a natural polymethoxyflavonoid isolated from the peel of citrus (Citrus reticulata) and has various biological activities, including radiosensitization, antiviral and anti-inflammatory effects [1][2][3]. Its radiosensitization mechanism in gastric cancer involves inhibiting the STAT3 signaling pathway and inhibiting radiation-induced EMT [1]. Its antiviral effect against respiratory syncytial virus (RSV) is achieved by blocking viral replication and reducing RSV-induced pro-inflammatory cytokine production [2]. It inhibits mast cell activation by inhibiting the NF-κB and MAPK (ERK1/2, JNK, p38) signaling pathways, thereby reducing allergic and inflammatory responses [3]. This compound has potential applications in gastric cancer radiotherapy, RSV infection treatment and disease management. Inflammatory/allergic diseases [1][2][3]
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| Molecular Formula |
C20H20O7
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| Molecular Weight |
372.37
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| Exact Mass |
372.12
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| CAS # |
481-53-8
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| Related CAS # |
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| PubChem CID |
68077
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
565.3±50.0 °C at 760 mmHg
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| Melting Point |
155 °C
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| Flash Point |
248.4±30.2 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.566
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| LogP |
2.66
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
27
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| Complexity |
540
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
ULSUXBXHSYSGDT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3
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| Chemical Name |
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6855 mL | 13.4275 mL | 26.8550 mL | |
| 5 mM | 0.5371 mL | 2.6855 mL | 5.3710 mL | |
| 10 mM | 0.2686 mL | 1.3428 mL | 2.6855 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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