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Sterigmatocystin

CAS# 10048-13-2

Sterigmatocystin

2D Structure

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Quality Control of Sterigmatocystin

3D structure

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Sterigmatocystin

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Chemical Properties of Sterigmatocystin

Cas No. 10048-13-2 SDF Download SDF
PubChem ID 5280389 Appearance Powder
Formula C18H12O6 M.Wt 324.29
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES COC1=C2C(=C3C4C=COC4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
Standard InChIKey UTSVPXMQSFGQTM-DCXZOGHSSA-N
Standard InChI InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
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 Sterigmatocystin

The grains.

Biological Activity of Sterigmatocystin

Description1. Sterigmatocystin , a mycotoxin commonly found in foodstuff and feedstuff, has been shown to be a carcinogenic mycotoxin in animal models. 2. Sterigmatocystin shows different toxicological, mutagenic and carcinogenic effects in animals and has been recognized as a 2B carcinogen (possible human carcinogen) by International Agency for Research on Cancer. 3. Sterigmatocystin has certain inhibiting effects on the secretion of IL-2 of human peripheral blood mononuclear cells (HPBMc) in vitro.
TargetsJNK | ERK | PI3K | mTOR | Akt | IL Receptor

Sterigmatocystin Dilution Calculator

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Sterigmatocystin Molarity Calculator

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Preparing Stock Solutions of Sterigmatocystin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0837 mL 15.4183 mL 30.8366 mL 61.6732 mL 77.0915 mL
5 mM 0.6167 mL 3.0837 mL 6.1673 mL 12.3346 mL 15.4183 mL
10 mM 0.3084 mL 1.5418 mL 3.0837 mL 6.1673 mL 7.7091 mL
50 mM 0.0617 mL 0.3084 mL 0.6167 mL 1.2335 mL 1.5418 mL
100 mM 0.0308 mL 0.1542 mL 0.3084 mL 0.6167 mL 0.7709 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 Sterigmatocystin

Cytotoxic and mutagenic effects of sterigmatocystin on cultured Chinese hamster cells.[Pubmed:7296761]

Carcinogenesis. 1981;2(10):945-9.

Cytotoxic and mutagenic effect of Sterigmatocystin (STC), a carcinogenic mycotoxin, on cultured Chinese hamster cells were investigated in the presence or absence of a metabolic activation system. STC directly applied to the cells induced cytotoxicity and drug-resistant mutations in a time- and concentration-dependent manner. Analyses of the effects of STC showed that treatment for shorter periods was more effective than that for longer periods. The presence of an activation system, cytotoxic and mutagenic effects of STC were strongly enhanced, and 1% of the microsome fraction was most efficient in inducing the effects. Analyses by equitoxic comparison showed that there was little difference in mutagenic activity between the direct treatment and the treatment using an activation system.

Involvement of MAPK and PI3K signaling pathway in sterigmatocystin-induced G2 phase arrest in human gastric epithelium cells.[Pubmed:21287681]

Mol Nutr Food Res. 2011 May;55(5):749-60.

SCOPE: Sterigmatocystin (ST), a mycotoxin commonly found in foodstuff and feedstuff, has been shown to be a carcinogenic mycotoxin in animal models. Many studies showed that the high level of ST contamination in grains might be related to the high incidence of gastric carcinoma in rural areas of China. However, up to now, the potential effects of ST on human gastric epithelium cells remain largely unknown. In this study, we explored the effects of ST on cell-cycle distribution and the regulatory mechanism in immortalized human gastric epithelium cells (GES-1). METHODS AND RESULTS: The effects of ST on the cell cycle distribution of GES-1 cells were determined with flow cytometric (FCM) analysis, Giemsa staining and immunofluorescence staining, while that on the expression of related gene-Cdc25C, Cdc2, CyclinB1 and the complex of CyclinB1-Cdc2 were studied with Western blot, reverse transcription polymerase chain reaction (RT-PCR) and immunoprecipitation assay respectively. We found that ST induced GES-1 cells arrested at G2 phase by regulating the expression of Cdc25C, Cdc2, CyclinB1 and the formation of CyclinB1-Cdc2 complex. Further study suggested JNK, ERK and PI3K/AKT/mTOR pathways to be involved in the process of G2 arrest induced by ST. The specific inhibitors of JNK and ERK reversed the role of ST, whereas that of PI3K/AKT/mTOR reinforced the effect of ST on cell-cycle distribution. CONCLUSION: This study demonstrates that JNK, ERK and PI3K/AKT/mTOR pathways participated in the G2 arrest induced by ST through the deregulation of CyclinB1, Cdc2 and Cdc25C. It may play some roles in the gastric carcinogenesis in ST exposure populations.

[Effects of sterigmatocystin on interleukin-2 secretion of human peripheral blood mononuclear cells in vitro].[Pubmed:12561545]

Wei Sheng Yan Jiu. 2002 Apr;31(2):112-4.

Sterigmatocystin (ST) is one of predominant contaminating mycotoxins in foodstuffs and grains of high incidence areas of malignant tumors in China. The effect of ST on interleukin-2 (IL-2) secretion of human peripheral blood mononuclear cells (HPBMc) in vitro was determined with enzyme-linked immunosorbent assay (ELISA) method to explore its putative effects on human immune function. ELISA analysis revealed that ST treatment generally showed negative effects on the IL-2 secretion of HPBMc in vitro. As the ST concentration changes, the inhibiting effects were different. The inhibiting effects at low concentrations (0.03125-0.125 mg/L) and high concentrations (1-2 mg/L) were stronger than the other concentrations(P < 0.05). The time-effect analysis (ST 1 mg/L) showed that inhibiting effects of ST on IL-2 secretion of HPBMc could be seen to a variable degree from 1 to 64 h after ST treatment, while a significant time-effect correlation could be found from 8 to 64 h (r = 0.822, P < 0.05). The results obtained in present study showed that ST has certain inhibiting effects on the secretion of IL-2 of HPBMc in vitro.

Sterigmatocystin: occurrence in foodstuffs and analytical methods--an overview.[Pubmed:19998385]

Mol Nutr Food Res. 2010 Jan;54(1):136-47.

Sterigmatocystin (STC) is a mycotoxin produced by fungi of many different Aspergillus species. Other species such as Bipolaris, Chaetomium, Emiricella are also able to produce STC. STC producing fungi were frequently isolated from different foodstuffs, while STC was regularly detected in grains, corn, bread, cheese, spices, coffee beans, soybeans, pistachio nuts, animal feed and silage. STC shows different toxicological, mutagenic and carcinogenic effects in animals and has been recognized as a 2B carcinogen (possible human carcinogen) by International Agency for Research on Cancer. There are more than 775 publications available in Scopus (and more than 505 in PubMed) mentioning STC, but there is no summary information available about STC occurrence and analysis in food. This review presents an overview of the worldwide information on the occurrence of STC in different foodstuffs during the last 40 years, and describes the progress made in analytical methodology for the determination of STC in food.

Description

Sterigmatocystine is a precursor of aflatoxins and a mycotoxin produced by common mold strains from Aspergillus versicolor. Sterigmatocystine, a inhibitor of G1 Phase and DNA synthesis, is used to inhibit p21 activity. Sterigmatocystine has teratogenic, and carcinogenic effects in animals.

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