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SML0724

Bikaverin

Name: Bikaverin
Brand: SIGMA

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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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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

SMILES string

[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

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.

Bikaverin is a red pigment with a polyketide tetracyclic benzoxanthone structure. Bikaverin has an antibiotic activity against some protozoa and fungi.

Preparation Note

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

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

Regulatory Information

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Effects of selected secondary metabolites of Fusarium moniliforme on unscheduled synthesis of DNA by rat primary hepatocytes.

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)

The polyketide synthase gene pks4 from Gibberella fujikuroi encodes a key enzyme in the biosynthesis of the red pigment bikaverin.

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

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)

Aeration affects acetate destination in Gibberella fujikuroi.

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

Adenylyl cyclase regulates heavy metal sensitivity, bikaverin production and plant tissue colonization in Fusarium proliferatum.

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

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Global Trade Item Number

SKU	GTIN
SML0724-1MG	04061837101366

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