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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

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
049M4040V
14181107
14130905
093M4034V
32130902

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Philipp Wiemann et al.
Molecular microbiology, 72(4), 931-946 (2009-04-30)
Fusarium secondary metabolites are structurally diverse, have a variety of activities and are generally poorly understood biosynthetically. The F. fujikuroi polyketide synthase gene bik1 was previously shown to be responsible for formation of the mycelial pigment bikaverin. Here we present
S Teichert et al.
Molecular microbiology, 53(6), 1661-1675 (2004-09-03)
In Gibberella fujikuroi, the gibberellin (GA) and bikaverin biosynthesis are under control of nitrogen metabolite repression. However, the signalling components acting upstream of AREA are still unknown. We investigated the role of glutamine synthetase (GS) both as an enzyme and
M Carmen Limón et al.
Applied microbiology and biotechnology, 87(1), 21-29 (2010-04-09)
Bikaverin is a reddish pigment produced by different fungal species, most of them from the genus Fusarium, with antibiotic properties against certain protozoa and fungi. Chemically, bikaverin is a polyketide with a tetracyclic benzoxanthone structure, resulting from the activity of
Naoko Nishimura et al.
Biological & pharmaceutical bulletin, 33(8), 1430-1433 (2010-08-06)
Plasma hyaluronan-binding protein (PHBP), a serine protease that can activate coagulation factor VII and prourokinase, circulates as a single-chain form (pro-PHBP), and is autoproteolytically converted to an active two-chain form with the aid of an effector such as spermidine and
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
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