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SML0724

Sigma-Aldrich

Bikaverin

from Fusarium subglutinans, ≥98% (HPLC)

Synonyme(s) :

6,11-Dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-7,10, 12-trione, Lycopersin, NSC 215139

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About This Item

Formule empirique (notation de Hill):
C20H14O8
Numéro CAS:
33390-21-5
Poids moléculaire :
382.32
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Source biologique

Fusarium subglutinans

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: 0.5 mg/mL (may require sonication and heating)
chloroform: 0.5 mg/mL
dichloromethane: 0.5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[o]1c2c([c](c4c1cc(cc4C)OC)=O)c(c3c(c2O)C(=O)C(=CC3=O)OC)O

InChI

1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3

Clé InChI

ZOQMSOSJEWBMHP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

Bikaverin is a red pigment with a polyketide tetracyclic benzoxanthone structure. Bikaverin has an antibiotic activity against some protozoa and fungi and also inhibits Succinate- and NAD-linked respiration in rat mitochondria at 20 mg/mL. At higher concentrations (50 mg/mL) it acts as an oxidative phosphorylation uncoupling agent of tumor cells and isolated rat liver mitochondria. Bikaverin demonstrates antitumor activity on Erlich ascites carcinoma (EAC), leukemia and sarcoma cells.

Reconstitution

Soluble in DMSO (0.5 mg/mL, may require sonication and heating). For further dilution, water based solutions can be used. Chloroform (0.5 mg/mL) and dichloromethane (0.5 mg/mL).

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Conseils de prudence

P301 + P310

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Pia Linnemannstöns et al.
Fungal genetics and biology : FG & B, 37(2), 134-148 (2002-11-01)
The ascomycete Gibberella fujikuroi mating population C (MP-C) is well known for the production of gibberellins, but also produces many other secondary metabolites, including the red polyketide pigment bikaverin. Here, we used a differential display method to clone a polyketide
W Giordano et al.
FEMS microbiology letters, 180(1), 111-116 (1999-11-05)
Gibberellins, fatty acids and the polyketides bikaverin and fusarin C are synthesized from a common precursor, acetyl-CoA. The production of these compounds in Gibberella fujikuroi was strongly influenced by aeration, determined by the air/medium ratio in shaken batch cultures. Higher
W P Norred et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 30(3), 233-237 (1992-03-01)
The Fusarium moniliforme mycotoxins--fusarin C, fumonisin B1, moniliformin and bikaverin--were evaluated for genotoxicity by their ability to induce unscheduled DNA synthesis (UDS) in primary rat hepatocytes. Isolated hepatocytes were exposed to several concentrations of moniliformin (5.0-500 microM), bikaverin (1.0-500 microM)
Takayoshi Saruwatari et al.
The Journal of antibiotics, 64(1), 9-17 (2010-11-26)
Fungal polyketide synthases (PKSs) catalyze a carbon-carbon bond forming reaction in an iterative manner using a variety of acyl-CoA molecules as substrates when biosynthesizing complex polyketides. Although most members from this class of natural products exhibit notable biological activities, often
Dominik Wagner et al.
Eukaryotic cell, 9(10), 1588-1601 (2010-08-24)
In Fusarium fujikuroi, bikaverin (BIK) biosynthesis is subject to repression by nitrogen. Unlike most genes subject to nitrogen metabolite repression, it has been shown that transcription of bik biosynthetic genes is not AreA dependent. Searching for additional transcription factors that
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