Citreoviridin

Molecular Formula

C23H30O6

M.W.

402.48

CAS number

25425-12-1

Details

Source

Penicillium sp.

Fermentek product Code

CIR-001

Brand/grade

For research

Specifications

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

Chemical identification

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

RTECS: UQ1235000

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

Further Information

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.

Retest time

2 Years

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