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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

Related Categories

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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

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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Alejandro F Estrada et al.
Fungal genetics and biology : FG & B, 45(5), 705-718 (2008-01-22)
The fungal proteins of the White Collar photoreceptor family, represented by WC-1 from Neurospora crassa, mediate the control by light of different biochemical and developmental processes, such as carotenogenesis or sporulation. Carotenoid biosynthesis is induced by light in the gibberellin-producing
A G Medentsev et al.
Prikladnaia biokhimiia i mikrobiologiia, 41(5), 573-577 (2005-10-26)
We studied biosynthesis of colored naphthoquinone metabolites by Fusarium decemcellulare, F. graminearum, and F. bulbigenum fungi. F. bulbigenum and F. graminearum synthesized bikaverin and aurofusarin, respectively, which depended on the conditions of cultivation. F. decemcellulare synthesized soluble extracellular naphthoquinones of
Roberto Rodríguez-Ortiz et al.
Applied microbiology and biotechnology, 85(6), 1991-2000 (2009-10-20)
The fungus Fusarium fujikuroi (Gibberella fujikuroi mating group C) exhibits a rich secondary metabolism that includes the synthesis of compounds of biotechnological interest, such as gibberellins, bikaverin, and carotenoids. The effect of the carbon source on their production was checked
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
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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