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SML0724

Sigma-Aldrich

Bikaverin

from Fusarium subglutinans, ≥98% (HPLC)

Synonym(e):

6,11-Dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-7,10, 12-trione, Lycopersin, NSC 215139

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About This Item

Empirische Formel (Hill-System):
C20H14O8
CAS-Nummer:
33390-21-5
Molekulargewicht:
382.32
UNSPSC-Code:
12352200
NACRES:
NA.77

Biologische Quelle

Fusarium subglutinans

Qualitätsniveau

200

Assay

≥98% (HPLC)

Form

powder

Löslichkeit

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

Lagertemp.

−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

InChIKey

ZOQMSOSJEWBMHP-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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.

Rekonstituierung

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).

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

P-Sätze

P301 + P310

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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)
Roberto Rodríguez-Ortiz et al.
Applied and environmental microbiology, 75(2), 405-413 (2008-12-03)
The fungus Fusarium fujikuroi (Gibberella fujikuroi MP-C) produces metabolites of biotechnological interest, such as gibberellins, bikaverins, and carotenoids. Gibberellin and bikaverin productions are induced upon nitrogen exhaustion, while carotenoid accumulation is stimulated by light. We evaluated the effect of nitrogen
Dominik Wagner et al.
Eukaryotic cell, 9(10), 1588-1601 (2010-08-24)
In Fusarium fujikuroi, bikaverin (BIK) biosynthesis is subject to repression by nitrogen. Unlike most genes subject to nitrogen metabolite repression, it has been shown that transcription of bik biosynthetic genes is not AreA dependent. Searching for additional transcription factors that
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
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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