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Cytosporone B

CAS# 321661-62-5

Cytosporone B

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Quality Control of Cytosporone B

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Chemical structure

Cytosporone B

3D structure

Chemical Properties of Cytosporone B

Cas No. 321661-62-5 SDF Download SDF
PubChem ID 10687292 Appearance Powder
Formula C18H26O5 M.Wt 322.4
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Csn-B; Dothiorelone G
Solubility DMSO : ≥ 100 mg/mL (310.17 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name ethyl 2-(3,5-dihydroxy-2-octanoylphenyl)acetate
SMILES CCCCCCCC(=O)C1=C(C=C(C=C1CC(=O)OCC)O)O
Standard InChIKey UVVWQQKSNZLUQA-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H26O5/c1-3-5-6-7-8-9-15(20)18-13(11-17(22)23-4-2)10-14(19)12-16(18)21/h10,12,19,21H,3-9,11H2,1-2H3
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 Cytosporone B

The peel of Aegiceras corniculata

Biological Activity of Cytosporone B

DescriptionCytosporone B is a naturally occurring agonist for Nur77, it also is a Salmonella pathogenicity island 1 (SPI-1)-inhibitor, it may have potential in drug development against antibiotic-resistant Salmonella. Cytosporone B can elevate blood glucose levels in fasting C57 mice, an effect that is accompanied by induction of multiple genes involved in gluconeogenesis. Cytosporone B can inhibit transforming growth factor-b (TGF-β)-induced contraction of human corneal fibroblasts (HCFs), likely as a result of its attenuation of the up-regulation of α-SMA expression.
TargetsTGF-β/Smad | Antifection | Nur77 | α-SMA | SPI-1
In vitro

Cytosporone B, an Inhibitor of the Type III Secretion System of Salmonella enterica Serovar Typhimurium[Reference: WebLink]

Antimicrobial Agents & Chemotherapy, 2013 , 57 (5) :2191-8.


METHODS AND RESULTS:
In this study, we identified several analogs of Cytosporone B (Csn-B) that strongly block the secretion of Salmonella pathogenicity island 1 (SPI-1)-associated effector proteins, without affecting the secretion of flagellar protein FliC in vitro. Csn-B and two other derivatives exhibited a strong inhibitory effect on SPI-1-mediated invasion to HeLa cells, while no significant toxicity to bacteria was observed. Nucleoid proteins Hha and H-NS bind to the promoters of SPI-1 regulator genes hilD, hilC, and rtsA to repress their expression and consequently regulate the expression of SPI-1 apparatus and effector genes. We found that Csn-B upregulated the transcription of hha and hns, implying that Csn-B probably affected the secretion of effectors through the Hha–H-NS regulatory pathway.
CONCLUSIONS:
In summary, this study presented an effective SPI-1 inhibitor, Csn-B, which may have potential in drug development against antibiotic-resistant Salmonella.

In vivo

Cytosporone B is an agonist for nuclear orphan receptor Nur77.[Pubmed: 18690216 ]

Nat Chem Biol. 2008 Sep;4(9):548-56.

Nuclear orphan receptor Nur77 has important roles in many biological processes. However, a physiological ligand for Nur77 has not been identified.
METHODS AND RESULTS:
Here, we report that the octaketide Cytosporone B (Csn-B) is a naturally occurring agonist for Nur77. Csn-B specifically binds to the ligand-binding domain of Nur77 and stimulates Nur77-dependent transactivational activity towards target genes including Nr4a1 (Nur77) itself, which contains multiple consensus response elements allowing positive autoregulation in a Csn-B-dependent manner. Csn-B also elevates blood glucose levels in fasting C57 mice, an effect that is accompanied by induction of multiple genes involved in gluconeogenesis. These biological effects were not observed in Nur77-null (Nr4a1-/-) mice, which indicates that Csn-B regulates gluconeogenesis through Nur77. Moreover, Csn-B induced apoptosis and retarded xenograft tumor growth by inducing Nur77 expression, translocating Nur77 to mitochondria to cause cytochrome c release.
CONCLUSIONS:
Thus, Csn-B may represent a promising therapeutic drug for cancers and hypoglycemia, and it may also be useful as a reagent to increase understanding of Nur77 biological function.

Protocol of Cytosporone B

Kinase Assay

Cytosporone B inhibits the TGF-β–induced expression of a–smooth muscle actin and contractility in human corneal fibroblasts.[Reference: WebLink]

Investigative Ophthalmology & Visual Science, 2016, 57(12):2363.

Cytosporone B (CsnB) is an antagonist for the nuclear receptor transcription factor NR4A1, known as Nur77, which contributes to the regulation of apoptosis and glucose homeostasis. Recently, it is reported that NR4A1 is related to tissue scarring by regulating transforming growth factor–b (TGF-β) signaling.
METHODS AND RESULTS:
To investigate the role of NR4A1 in human corneal fibroblasts (HCFs), we examined the effects of CsnB on the expression of a–smooth muscle actin (α-SMA) and contractility in these cells induced by stimulation with TGF-β. Cytosporone B inhibited TGF-β–induced contraction of HCFs, likely as a result of its attenuation of the up-regulation of α-SMA expression.
CONCLUSIONS:
Our results suggest that NR4A1 mediates these effects of TGF-β in HCFs, and that CsnB warrants further investigation as a potential therapeutic modulator of corneal stromal contraction and scarring.

Cytosporone B Dilution Calculator

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Cytosporone B Molarity Calculator

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Preparing Stock Solutions of Cytosporone B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1017 mL 15.5087 mL 31.0174 mL 62.0347 mL 77.5434 mL
5 mM 0.6203 mL 3.1017 mL 6.2035 mL 12.4069 mL 15.5087 mL
10 mM 0.3102 mL 1.5509 mL 3.1017 mL 6.2035 mL 7.7543 mL
50 mM 0.062 mL 0.3102 mL 0.6203 mL 1.2407 mL 1.5509 mL
100 mM 0.031 mL 0.1551 mL 0.3102 mL 0.6203 mL 0.7754 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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Background on Cytosporone B

Cytosporone B (Csn-B;Dothiorelone G) is a naturally occurring nuclear orphan receptor Nur77 agonist with an EC50 of 0.278 nM.

In Vitro:Cytosporone B targets the ligand binding domain of Nur77, which selectively stimulates the transactivational activity of Nur77. Cytosporone B induces luciferase activity in cells that are cotransfected with GAL4- Nur77 or GAL4-LBD. The EC50 of cytosporone B for Nur77 is 0.278 nM. Cytosporone B displays robust pro-apoptotic activity in gastric cancer cells BGC-823. 63.5% of the cells are apoptotic when treated with cytosporone B for 48 h. Cytosporone B shows selective effect on cancerous cells. Cytosporone B inhibits proliferation of human gastric cancer BGC-823 cells and human colon cancer SW620 cells by 470%, but it has a modest effect on human lung cancer H1299 cells and human hepatoma HepG2 cells[1].

In Vivo:In the hepatocytes of wild-type mice, the transcriptional activity of the reporter is induced five-fold with cytosporone B treatment. In wild-type mice, cytosporone B treatment significantly increases glucose levels from 3.2 to 11.4 mM within the first 30 min, and thereafter blood glucose gradually decreased before reaching the initial level after 300 min[1].

References:
[1]. Zhan Y, et al. Cytosporone B is an agonist for nuclear orphan receptor Nur77. Nat Chem Biol. 2008 Sep;4(9):548-56.

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References on Cytosporone B

Cytosporone B is an agonist for nuclear orphan receptor Nur77.[Pubmed:18690216]

Nat Chem Biol. 2008 Sep;4(9):548-56.

Nuclear orphan receptor Nur77 has important roles in many biological processes. However, a physiological ligand for Nur77 has not been identified. Here, we report that the octaketide Cytosporone B (Csn-B) is a naturally occurring agonist for Nur77. Csn-B specifically binds to the ligand-binding domain of Nur77 and stimulates Nur77-dependent transactivational activity towards target genes including Nr4a1 (Nur77) itself, which contains multiple consensus response elements allowing positive autoregulation in a Csn-B-dependent manner. Csn-B also elevates blood glucose levels in fasting C57 mice, an effect that is accompanied by induction of multiple genes involved in gluconeogenesis. These biological effects were not observed in Nur77-null (Nr4a1-/-) mice, which indicates that Csn-B regulates gluconeogenesis through Nur77. Moreover, Csn-B induced apoptosis and retarded xenograft tumor growth by inducing Nur77 expression, translocating Nur77 to mitochondria to cause cytochrome c release. Thus, Csn-B may represent a promising therapeutic drug for cancers and hypoglycemia, and it may also be useful as a reagent to increase understanding of Nur77 biological function.

Orphan nuclear receptor NR4A1 regulates transforming growth factor-beta signaling and fibrosis.[Pubmed:25581517]

Nat Med. 2015 Feb;21(2):150-8.

Mesenchymal responses are an essential aspect of tissue repair. Failure to terminate this repair process correctly, however, results in fibrosis and organ dysfunction. Therapies that block fibrosis and restore tissue homeostasis are not yet available for clinical use. Here we characterize the nuclear receptor NR4A1 as an endogenous inhibitor of transforming growth factor-beta (TGF-beta) signaling and as a potential target for anti-fibrotic therapies. NR4A1 recruits a repressor complex comprising SP1, SIN3A, CoREST, LSD1, and HDAC1 to TGF-beta target genes, thereby limiting pro-fibrotic TGF-beta effects. Even though temporary upregulation of TGF-beta in physiologic wound healing induces NR4A1 expression and thereby creates a negative feedback loop, the persistent activation of TGF-beta signaling in fibrotic diseases uses AKT- and HDAC-dependent mechanisms to inhibit NR4A1 expression and activation. Small-molecule NR4A1 agonists can overcome this lack of active NR4A1 and inhibit experimentally-induced skin, lung, liver, and kidney fibrosis in mice. Our data demonstrate a regulatory role of NR4A1 in TGF-beta signaling and fibrosis, providing the first proof of concept for targeting NR4A1 in fibrotic diseases.

Description

Cytosporone B (Csn-B; Dothiorelone G) is a naturally occurring nuclear orphan receptor Nur77/NR4A1 agonist with an EC50 of 0.278 nM.

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