| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Matrix metalloproteinase 1 (MMP-1) / Collagenase-1. [1]
ERK (Extracellular signal-regulated kinase), JNK (c-Jun N-terminal kinase), c-Jun. [1] |
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| ln Vitro |
In human dermal fibroblast neonatal (HDFn) cells, 3,5,6,7,8,3',4'-Heptamethoxyflavone (HMF) (at 50, 100, 200 µg/mL) significantly inhibited cellular collagenase activity. At 200 µg/mL, HMF showed approximately two times higher inhibitory activity than epigallocatechin gallate (EGCG) at the same concentration. [1]
HMF (at 50, 100, 200 µg/mL) significantly increased the type I procollagen content in UVB-induced HDFn cells in a dose-dependent manner. The amounts were 0.46 ± 0.01, 0.56 ± 0.04, and 0.61 ± 0.01 µg/mL at 50, 100, and 200 µg/mL, respectively. [1] Western blot analysis showed that HMF (at 50, 100, 200 µg/mL) significantly suppressed the expression of MMP-1 protein and induced the expression of type I procollagen protein in UVB-induced HDFn cells in a dose-dependent manner. The relative expression of type I procollagen after pretreatment with 200 µg/mL of HMF was about 5.5 times higher than that of non-treated UV-induced HDFn cells. [1] HMF (at 50, 100, 200 µg/mL) significantly decreased the phosphorylation levels of ERK, JNK, and c-Jun proteins in UVB-induced HDFn cells. It also significantly inhibited the expression of c-Fos protein. However, HMF did not affect the phosphorylation or expression of p38 protein. [1] HMF (at 50, 100, 200 µg/mL) increased the expression of Smad3 protein and decreased the expression of Smad7 protein in UVB-induced HDFn cells in a dose-dependent manner. [1] |
| Enzyme Assay |
The cellular collagenase activity assay was performed. HDFn cell pellets were suspended in 0.1 M Tris-HCl buffer (pH 7.4) containing 0.1% Triton X-100 and 1 mM phenylmethylsulfonyl fluoride, then disrupted by sonication. The reaction mixture contained HMF (100 and 200 µg/mL), 0.1 M Tris-HCl (pH 7.5) including 4 mM CaCl2, 4-phenylazo-benzyloxy-carbonyl-Pro-Leu-Gly-Pro-D-Arg (Pz-peptide) substrate, and the cell-free supernatant. The mixture was incubated at 37°C for 20 minutes, and the reaction was stopped by adding a citric acid stop solution. Ethyl acetate was added, and the absorbance of the supernatant was measured at 320 nm. Collagenase inhibitory activity was calculated as a percentage. [1]
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| Cell Assay |
For cell viability assessment, HDFn cells were incubated with various concentrations of HMF (50, 100, 200, and 400 µg/mL) for 24 hours. An MTT solution was added to each well and incubated for 3 hours. The resulting formazan crystals were dissolved in dimethyl sulfoxide (DMSO), and absorbance was measured at 570 nm. HMF showed no cytotoxic effects up to 200 µg/mL, but cell viability was significantly reduced at 400 µg/mL. [1]
For the type I procollagen content assay, HDFn cells were seeded in 6-well plates and allowed to attach. Cells were incubated with HMF (50, 100, and 200 µg/mL) for 24 hours in serum-free media, then washed, irradiated with UVB (20 mJ/cm²), and further incubated for 24 hours. The cell-free supernatant was collected, diluted, and mixed with an antibody-horseradish peroxidase conjugate solution in an antibody-coated 96-well plate. After incubation, the plate was rinsed, incubated with a substrate solution containing hydrogen peroxide and tetramethylbenzidine in the dark, and the reaction was stopped with sulfuric acid. Absorbance was measured at 450 nm. [1] For western blot analysis, HDFn cell pellets were lysed, and total protein concentration was determined. Equal amounts of protein were separated by SDS-PAGE and transferred to a nitrocellulose membrane. The membrane was blocked, incubated with primary antibodies (against ERK, p-ERK, p38, p-p38, JNK, p-JNK, c-Jun, p-c-Jun, c-Fos, Smad3, Smad7, type I procollagen, MMP-1, and actin) overnight at 4°C, followed by incubation with HRP-conjugated secondary antibodies. Signals were visualized using enhanced chemiluminescence and quantified. [1] |
| Toxicity/Toxicokinetics |
In HDFn cells, concentrations of 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF) at up to 200 µg/mL did not show cytotoxic effects after 24 hours of treatment. However, at concentrations of 400 µg/mL, HMF significantly reduced cell viability, resulting in approximately 50% cell death compared to untreated cells. [1]
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| References |
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| Additional Infomation |
3-Methoxynorbiglitin belongs to the flavonoid class and is an ether compound. It has been reported that 3,3',4',5,6,7,8-heptamethoxyflavone is found in Melicope triphylla, Citrus reticulata, and other organisms with relevant data. See also: orange peel (partial); sour orange (Citrus aurantium) peel (partial). 3,5,6,7,8,3',4'-Heptamethoxyflavone (HMF) is a polymethoxyflavone isolated from the peel of Satsuma mandarin oranges (Citrus unshiu). [1]
The mechanism of its anti-photoaging effect is believed to be the inhibition of the MAPK signaling pathway (especially the reduction of phosphorylation levels of ERK, JNK and c-Jun) and the regulation of the TGF-β/Smad signaling pathway (increasing Smad3 expression and decreasing Smad7 expression), thereby leading to the downregulation of MMP-1 expression and the upregulation of type I procollagen expression in UVB-induced human dermal fibroblasts. [1] This study shows that HMF has the potential to act as a skin care agent to prevent UV-induced photoaging of the skin. [1] |
| Molecular Formula |
C22H24O9
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|---|---|
| Molecular Weight |
432.4206
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| Exact Mass |
432.142
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| CAS # |
1178-24-1
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| PubChem CID |
150893
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
618.7±55.0 °C at 760 mmHg
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| Melting Point |
129 - 131 °C
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| Flash Point |
268.0±31.5 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.576
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| LogP |
1.59
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
31
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| Complexity |
651
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
SSXJHQZOHUYEGD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3
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| Chemical Name |
2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ~50 mg/mL (~115.63 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (5.78 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.78 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 | 2.3126 mL | 11.5628 mL | 23.1257 mL | |
| 5 mM | 0.4625 mL | 2.3126 mL | 4.6251 mL | |
| 10 mM | 0.2313 mL | 1.1563 mL | 2.3126 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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