Citreoviridin
Molecular Formula
C23H30O6
M.W.
402.48
CAS number
25425-12-1
Source
Penicillium sp.
Fermentek product Code
CIR-001
Brand/grade
For research
Appearance
Yellow to Orange-yellow powder
Purity by HPLC
≥95% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
107°C-112°C
Solubility test
Clear yellow solution at 10mg/ml of DMSO, Methanol or Dichloromethane
Names and identifiers

Synonyms

  • Citreoviridin A
  • 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

 RTECSUQ1235000

EU number
636-737-5
Chemical name
Citreoviridin
Description

Citreoviridin is a neurotoxic mycotoxin from Penicillium citeoviride, Penicillium toxicarium, Penicillium ochrosalmoneum, Penicillium ochrosalmoneum, Aspergillus terreus, and several other related fungi. Citreoviridin is believed to be the cause of the Acute Cardiac Beri-Beri disease. Naturally, It is formed on rice improperly stored.

InChl Key
JLSVDPQAIKFBTO-OMCRQDLASA-N
Canonical SMILES
CC1C(C(C(O1)(C)C=C(C)C=CC=CC=CC2=C(C(=CC(=O)O2)OC)C)O)(C)O
Isomeric SMILES
C[C@@H]1[C@]([C@H]([C@](O1)(C)/C=C(\C)/C=C/C=C/C=C/C2=C(C(=CC(=O)O2)OC)C)O)(C)O
Solubility ( literature )

Citreoviridin is soluble in benzene, ethanol, chloroform, ether, dichloromethane. Citreoviridin is hardly soluble in water (enough to give it yellow color) and hexane

Compound Classification

Aurovertin class mycotoxin

Comment: Aurovertins are very toxic and complex pyrone derivatives of fungal origin . They bind to and inhibit mitochondrial ATPase, thereby uncoupling oxidative phosphorylation. They are used as biochemical tools.

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Hygroscopic substance.
Protect from moisture
Protect from light !
Open carefully.
Use the original container to store the product.
Keep the lid tightly closed.
Store under argon.
Other vendors may recommend higher temperatures for storage.
Applications

As other Aurovertin group members, Citreoviridin binds to and inhibit mitochondrial ATPase, thereby uncoupling oxidative phosphorylation.

Citreoviridin, a mycotoxin that has been shown to inhibit the mitochondrial ATP synthetase system. It inhibits soluble ATPase, ADP-stimulated respiration in isolated rat liver mitochondria, and ATP-driven reduction of NAD+ by succinate (KD = 2 µM). Citreoviridin has been used to target ectopic ATPase activity in cancer cells in order to modulate the metabolic activity associated with tumorigenesis.

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Warnings
Ingredient type
Fermentek product
Available since
Title
Transport information
Value
Pg II
Signal to sort
C