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Citreoviridin A

Citreoviridin A

Product ID C3576
Cas No. 25425-12-1
Purity ≥95%
Product Unit SizeCostQuantityStock
1 mg $161.20 In stock
5 mg $633.80 In stock
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Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

Citreoviridin A is a mycotoxin found in cereal and bread grains; it exhibits pro-oxidative, anticancer chemotherapeutic, antibacterial, antifungal, and antiviral activities. In vitro, citreoviridin A increases ROS levels and decreases glutathione, inducing oxidative stress, destabilizing the lysosome and mitochondria and causing DNA damage. Citreoviridin A inhibits the F1 subunit of F1F0 ATP synthase, inhibiting cell proliferation in a lung cancer xenograft model. Citreoviridin also increases phosphorylation of eIF2α, inducing the unfolded protein response and the inhibition of cell growth. In other cellular models, this compound increases TNF-α-induced cellular adhesion to monocytes, increases nuclear translocation of NF-κB, and increases expression of ICAM-1, VCAM-1, E-selectin, and MCP-1. Citreoviridin inhibits cellular growth in species of Bacillus and Candida and also inhibits replication of HIV-1.

Product Info

Cas No.

25425-12-1

Purity

≥95%

Formula

C23H30O6

Formula Wt.

402.48

Chemical Name

4-Methoxy-5-methyl-6-(7-methyl-8-(tetrahydro-3,4-dihydroxy-2,4,5-trimethyl-2-furyl)-1,3,5,7-octatetraenyl)-2H-pyran-2-one

IUPAC Name

6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4, 5-trimethyloxolan-2-yl]-7-methylocta-1,3,5, 7-tetraenyl]-4-methoxy-5-methylpyran-2-one

Synonym

Citreoviridin

Melting Point

110°C

Solubility

Insoluble in water. Soluble in ethanol, chloroform, dichloromethane, and DMSO (10 mg/mL).

Appearance

Orange-yellow powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

C3576 MSDS PDF

Info Sheet

C3576 Info Sheet PDF

References

Bai Y, Jiang LP, Liu XF, et al. The role of oxidative stress in citreoviridin-induced DNA damage in human liver-derived HepG2 cells. Environ Toxicol. 2013 Dec 6. [Epub ahead of print]. PMID: 24318808.

Wu YH, Hu CW, Chien CW, et al. Quantitative proteomic analysis of human lung tumor xenografts treated with the ectopic ATP synthase inhibitor citreoviridin. PLoS One. 2013 Aug 21;8(8):e70642. PMID: 23990911.

Hou H, Zhou R, Jia Q, et al. Citreoviridin enhances tumor necrosis factor-α-induced adhesion of human umbilical vein endothelial cells. Toxicol Ind Health. 2013 Mar 22. PMID: 23524880.

Chang HY, Huang HC, Huang TC, et al. Ectopic ATP synthase blockade suppresses lung adenocarcinoma growth by activating the unfolded protein response. Cancer Res. 2012 Sep 15;72(18):4696-706. PMID: 22822083.

Vieta I, Savarino A, Papa G, et al. In vitro inhibitory activity of citreoviridin against HIV-1 and an HIV-associated opportunist: Candida albicans. J Chemother. 1996 Oct;8(5):351-7. PMID: 8957714.

Sayood SF, Suh H, Wilcox CS, et al. Effect of citreoviridin and isocitreoviridin on beef heart mitochondrial ATPase. Arch Biochem Biophys. 1989 May 1;270(2):714-21. PMID: 2523213.

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