Artocarpin

CAS# 7608-44-8

Artocarpin

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Quality Control of Artocarpin

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Chemical structure

Artocarpin

3D structure

Chemical Properties of Artocarpin

Cas No. 7608-44-8 SDF Download SDF
PubChem ID 5458461 Appearance Yellow powder
Formula C26H28O6 M.Wt 436.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(E)-3-methylbut-1-enyl]-3-(3-methylbut-2-enyl)chromen-4-one
SMILES CC(C)C=CC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=C(C=C(C=C3)O)O)CC=C(C)C)OC
Standard InChIKey KRGDFVQWQJIMEK-RMKNXTFCSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Artocarpin

The heartwood of Artocarpus incisus

Biological Activity of Artocarpin

Description1. Artocarpin induces apoptosis in HSC-1 and T47D cells through modulation of MAPK and Akt/mTOR pathways, an extrinsic pathway , respectively . 2. Artocarpin has anti- bactericidal effect, can reduce the viability of pneumococci by a factor of >1000, without obvious harm to lung epithelial cells. 3. Artocarpin can prevent skin damage from UVB irradiation-induced photodamage in hairless mice and this is likely mediated through its antioxidant and anti-inflammation mechanisms. 4. Artocarpin possesses potent 5alpha reductase inhibitory effect. 5. Artocarpin has an efficient lightening effect on UV-stimulated hyperpigmented dorsal skins of brownish guinea pigs.
TargetsCOX | TNF-α | IL Receptor | Caspase | ERK | JNK | Akt | mTOR | p38MAPK

Artocarpin Dilution Calculator

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Artocarpin Molarity Calculator

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Preparing Stock Solutions of Artocarpin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.291 mL 11.4548 mL 22.9095 mL 45.819 mL 57.2738 mL
5 mM 0.4582 mL 2.291 mL 4.5819 mL 9.1638 mL 11.4548 mL
10 mM 0.2291 mL 1.1455 mL 2.291 mL 4.5819 mL 5.7274 mL
50 mM 0.0458 mL 0.2291 mL 0.4582 mL 0.9164 mL 1.1455 mL
100 mM 0.0229 mL 0.1145 mL 0.2291 mL 0.4582 mL 0.5727 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Artocarpin

Cytotoxic effect of artocarpin on T47D cells.[Pubmed:20544395]

J Nat Med. 2010 Oct;64(4):423-9.

In our screening projects for anticancer agents from natural resources, Artocarpin [6-(3-methyl-1-butenyl)-5,2',4'-trihydroxy-3-isoprenyl-7-methoxyflavone] isolated from wood of jack fruit (Artocarpus heterophyllus) showed potent cytotoxic activity on human T47D breast cancer cells. The mode of action of Artocarpin was evaluated by its effect on cell viability, nuclear morphology, cell cycle progression, expression of protein markers for apoptosis, and mitochondrial membrane potential (Delta psi m). These results showed that Artocarpin caused a reduction of cell viability in a concentration-dependent manner and an alteration of cell and nuclear morphology. Moreover, the percentage of the sub-G1 phase formation was elevated dose-dependently. Artocarpin induced activation of caspase 8 and 10 as indicated by stronger signal intensity of cleaved-caspase 8 and weaker signal intensity of caspase 10 markers detected after Artocarpin treatment. In addition, we also noticed the activation of caspase 3 by Artocarpin. There were negligible changes in mitochondrial membrane potential (Delta psi m) due to Artocarpin treatment. All together, these data indicated that Artocarpin induced apoptosis in T47D cells possibly via an extrinsic pathway.

The skin-lightening effects of artocarpin on UVB-induced pigmentation.[Pubmed:11842337]

Planta Med. 2002 Jan;68(1):79-81.

This study was conducted to evaluate the effects of the prenylated flavonol Artocarpin from the heartwood of Artocarpus incisus on ultraviolet (UV)-induced hyperpigmentation of guinea pig skin. An efficient lightening effect was observed following topical application of Artocarpin to UV-stimulated hyperpigmented dorsal skins of brownish guinea pigs.

Artocarpin attenuates ultraviolet B-induced skin damage in hairless mice by antioxidant and anti-inflammatory effect.[Pubmed:23871788]

Food Chem Toxicol. 2013 Oct;60:123-9.

Artocarpin, a prenylated flavonoid isolated from an agricultural plant Artocarpus communis, has been documented to possess anti-inflammation and anticancer activities. As oxidative stress and inflammation promote the development of ultraviolet B (UVB) irradiation-induced photodamage, the aim of the present study was to evaluate the photoprotective effect of Artocarpin on UVB-induced skin damage in hairless mice. Artocarpin at a topical dose of 0.05% and 0.1% showed a significant photoprotective effect by decreasing histopathological changes, such as desquamation, epidermal thicken and sunburn cell formation, but 0.1% of Artocarpin administration did not show better effect. Regarding the antioxidant activities, Artocarpin exhibited a significant effect (P<0.05) by decreasing levels of reactive species oxygen and lipid peroxidation. In addition, Artocarpin can significant decrease the level of tumor necrosis factor-alpha and interleukin-1beta for downregulating the inflammation protein, including the synthesis of cytosolic phospholipase A2 and cyclooxygenase-2 (P<0.05). In conclusion, these data suggest that Artocarpin can prevent skin damage from UVB irradiation-induced photodamage in hairless mice and this is likely mediated through its antioxidant and anti-inflammation mechanisms. Therefore, we suggested that Artocarpin could be a useful photoprotective agent in medicine and/or cosmetics.

Artocarpin Induces Apoptosis in Human Cutaneous Squamous Cell Carcinoma HSC-1 Cells and Its Cytotoxic Activity Is Dependent on Protein-Nutrient Concentration.[Pubmed:25648333]

Evid Based Complement Alternat Med. 2015;2015:236159.

Artocarpin, a natural prenylated flavonoid, has been shown to have various biological properties. However, its effects on human cutaneous squamous cell carcinoma (SCC) have not been previously investigated. We set out to determine whether Artocarpin has cytotoxic effects on SCC cells and whether its pharmacological activity is dependent on protein-nutrient concentration. Our results showed that treatment of HSC-1 cells (a human cutaneous SCC cell line) with Artocarpin decreased cell viability and induced cell apoptosis by increasing caspase 3/7 activity. These effects were more pronounced at low fetal bovine serum (FBS) concentrations. Artocarpin induced an increase in the level of phospho-p38 and a decrease in the levels of phospho-ERK, phospho-JNK, phospho-Akt, phospho-mTOR, and phospho-S6K. High FBS concentrations in the culture media inhibited and delayed the uptake of Artocarpin from the extracellular compartment (culture media) into the intracellular compartment, as determined by high performance liquid chromatography (HPLC) analysis. In conclusion, Artocarpin induces apoptosis in HSC-1 cells through modulation of MAPK and Akt/mTOR pathways. Binding of Artocarpin to proteins in the FBS may inhibit cellular uptake and reduce the cytotoxic activity of Artocarpin on HSC-1 cells. Therefore, Artocarpin may have potential use in the future as a form of treatment for cutaneous SCC.

Antipneumococcal activity of neuraminidase inhibiting artocarpin.[Pubmed:25592264]

Int J Med Microbiol. 2015 May;305(3):289-97.

Streptococcus (S.) pneumoniae is a major cause of secondary bacterial pneumonia during influenza epidemics. Neuraminidase (NA) is a virulence factor of both pneumococci and influenza viruses. Bacterial neuraminidases (NAs) are structurally related to viral NA and susceptible to oseltamivir, an inhibitor designed to target viral NA. This prompted us to evaluate the antipneumococcal potential of two NA inhibiting natural compounds, the diarylheptanoid katsumadain A and the isoprenylated flavone Artocarpin. Chemiluminescence, fluorescence-, and hemagglutination-based enzyme assays were applied to determine the inhibitory efficiency (IC(50) value) of the tested compounds towards pneumococcal NAs. The mechanism of inhibition was studied via enzyme kinetics with recombinant NanA NA. Unlike oseltamivir, which competes with the natural substrate of NA, Artocarpin exhibits a mixed-type inhibition with a Ki value of 9.70 muM. Remarkably, Artocarpin was the only NA inhibitor (NAI) for which an inhibitory effect on pneumococcal growth (MIC: 0.99-5.75 muM) and biofilm formation (MBIC: 1.15-2.97 muM) was observable. In addition, we discovered that the bactericidal effect of Artocarpin can reduce the viability of pneumococci by a factor of >1000, without obvious harm to lung epithelial cells. This renders Artocarpin a promising natural product for further investigations.

Targeted transfollicular delivery of artocarpin extract from Artocarpus incisus by means of microparticles.[Pubmed:17493791]

Eur J Pharm Biopharm. 2007 Nov;67(3):639-45.

Artocarpin (Ar), an extract of heartwood of Artocarpus incisus, possesses potent 5alpha reductase inhibitory effect. The penetration of Ar into the deeper layers of the skin where androgen receptors are present is limited. Therefore, this study was aimed to prepare alginate/chitosan (ACS) microparticles for targeted transfollicular delivery. It was found that a suitable particle size ranging from 2 to 6 microm can be prepared using the ionotropic gelation technique. Entrapment efficiency of Ar in ACS microparticles was 18.7+/-1.7%. The release of Ar from the ACS microparticles over 6 h was 0.7% of the loading dose suitable for a long-term release of Ar in the follicular ducts. The optimal growth suppression of the hamster flank organs could be achieved by topical application of Ar-ACS microparticles with a content of 0.1 mg in 5 mg microparticles to one hamster flank while the other flank (intraspecies control) showed the normal growth of the flank organs and Ar at the same concentration in solution form could not suppress the growth of the flank organs to the same extent. The efficiency of Ar 0.1 mg loaded in ACS microparticles was shown to be comparable to a dose of 1 mg Ar applied as solution. However, Ar formulated in microparticles did not show significant systemic action compared to the dermal application of an Ar solution and a flutamide preparation (1 mg) as positive control.

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