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Merck
CN

SML0724

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

Key Documents

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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

biological source

Fusarium subglutinans

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

Quality Level

200

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
049M4040V
14181107
14130905
093M4034V
32130902

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Mayra Mendonça et al.
Food chemistry: X, 12, 100136-100136 (2021-10-19)
Microbial pigments have a distinguished potential for applications in food and pharmaceutical industries, stimulating the research in this field. The present study evaluated the ideal conditions for extracting bikaverin (red pigment) from the biomass of Fusarium oxysporum CCT7620. Among the
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
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
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