| Source: |
Fusarium sp. |
| Synonyms |
IUPAC Name:
(3S,9S,15S)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexoneooctadecane-2,5,8,11,14,17-hexone
|
| Description: |
Beauvericin is a mycotoxin derived from the mould Beauveria bassiana, Fusarium strains and other moulds. Beauvericin belongs to the enniatin family of antibiotics. Beauvericin is a cyclic hexadepsipeptide with alternating L-N-methylphenylalanyl and D-a-hydroxyisovaleryl residues. |
| CAS number: | 26048-05-5 |
| Merck index: |
14: not listed |
| Molecular weight: |
783 |
| Structure: |
 |
| Molecular Formula: | C45H57N3O9 |
| Canonical SMILES: |
CC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O) N(C(C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C |
Solubility
information: |
Beauvericin insoluble in water but soluble in organic solvents. |
| Specifications | |
| Appearance: |
white crystalline powder |
| Purity: |
At least 96% by TLC, HPLC
Current lot 97.7% by HPLC |
| λmax: | |
| Melting point |
147 - 148°C |
| Solubility |
Clear colorless solution at 1 mg/ml of Methanol, Acetonitrile |
| Storage | 3-8°C. |
| Applications | Beauvericin is active against Gram+ bacteria, mycobacteria, insects, brine shrimp.
Beauvericin shows cytotoxic, Immunosuppressant, and apoptotic activity.
Beauvericin is the most potent specific inhibitor of cholesterol acyltransferase and possesses ionophoric properties.
Beauvericin increases ion permeability in biological membranes by forming a complex with essential cations (Ca2+, Na+, K+), which may affect the ionic homeostasis. |
| Classification | Oligopeptide, ionophore, antibiotic |
| Related products | |
| Warnings |
To the best of
our knowledge, the chemical, physical, and toxicological
properties have not been thoroughly
investigated.
This substance is not classified as dangerous according to
Directive 67/548/EEC.
|
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
Beauvericin by Fermentek is not produced from or contains any ingredients from animal origin.
No genetically modified organisms are used. |
| Publications | |
| |
Beauvericin
and enniatins H, I and MK1688 are new potent inhibitors of human
immunodeficiency virus type-1 integrase
The Journal of Antibiotics (2009) 62, 687–690
Cha-Gyun Shin, Dog-Gn An1, Hyuk-Hwan Song and Chan Lee |
| |
Chen BF, Tsai MC, Jow GM.
Induction of calcium influx from extracellular fluid by beauvericin in human leukemia cells.
Biochem Biophys Res Commun. 2006 Feb 3;340(1):134-9. |
| |
Kouri K, Duchen MR, Lemmens-Gruber R.
Effects of beauvericin on the metabolic state and ionic homeostasis of ventricular myocytes of the guinea pig.
Chem Res Toxicol. 2005 Nov;18(11):1661-8 |
| |
Lin HI, Lee YJ, Chen BF, Tsai MC, Lu JL, Chou CJ, Jow GM.
Involvement of Bcl-2 family, cytochrome c and caspase 3 in induction of apoptosis by beauvericin in human non-small cell lung cancer cells.
Cancer Lett. 2005 Dec 18;230(2):248-59. |
| |
Tang CY, Chen YW, Jow GM, Chou CJ, Jeng CJ
Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+.
Chem Res Toxicol. 2005 May;18(5):825-33 |
|
Beauvericin on Wikipedia
|
| Clinical perspectives of Beauvericin
J
Antibiot (Tokyo). 2009 Dec;62(12):687-90.
Shin CG, An DG, Song HH, Lee C. have shown that
Beauvericin has a clinical potential in treating AIDS, as it
inhibits the HIV integrase type-1.
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