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SML0724

Sigma-Aldrich

Bikaverin

from Fusarium subglutinans, ≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C20H14O8
CAS Number:
33390-21-5
Molecular Weight:
382.32
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Fusarium subglutinans

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

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

InChI key

ZOQMSOSJEWBMHP-UHFFFAOYSA-N

Biochem/physiol Actions

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).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Enzymatic synthesis of aromatic polyketides using PKS4 from Gibberella fujikuroi.
Suzanne M Ma et al.
Journal of the American Chemical Society, 129(35), 10642-10643 (2007-08-19)
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
Gábor Kohut et al.
Journal of basic microbiology, 50(1), 59-71 (2010-01-19)
A homologue of the adenylyl cyclase (AC) gene of Neurospora crassa, named Fpacy1 was cloned from the genomic library of Fusarium proliferatum ITEM 2287 by screening the library with a DNA fragment amplified by using PCR primers designed from conserved
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)
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