Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C45H57N3O9 |
| Molecular Weight | 783.9488 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC3=CC=CC=C3)N(C)C(=O)[C@H](OC(=O)[C@H](CC4=CC=CC=C4)N(C)C1=O)C(C)C)C(C)C
InChI
InChIKey=GYSCAQFHASJXRS-FFCOJMSVSA-N
InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1
| Molecular Formula | C45H57N3O9 |
| Molecular Weight | 783.9488 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23877026
https://www.ncbi.nlm.nih.gov/pubmed/25178661
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23877026
https://www.ncbi.nlm.nih.gov/pubmed/25178661
Beauvericin is a famous mycotoxin produced by many fungi, such as Beaveria bassiana and Fusarium spp. Beauvericin is a cyclic hexadepsipeptide (Figure 1) that belongs to the enniatin antibiotic family. It contains three D-hydroxyisovaleryl and three N-methylphenylalanyl residues in an alternating sequence. Beauvericin was first isolated from Beaveria bassiana, which is a common and commercial entomopathogenic mycoinsecticide. Beauvericin was one of the active constituents of B. bassiana and was confirmed to have antimicrobial and anti-tumor activities. Beauvericin has a strong antibacterial activity against human, animal and plant pathogenic bacteria with no selectively between Gram-positive and Gram-negative bacteria. The cytotoxicity of beauvericin to human tumor cells has been frequently reported.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL267 |
|||
Target ID: CHEMBL394 |
2.4 µM [EC50] | ||
Target ID: CHEMBL395 |
3.6 µM [EC50] | ||
Target ID: CHEMBL220 |
3.09 µM [IC50] | ||
Target ID: CHEMBL387 |
2.02 µM [IC50] | ||
Target ID: CHEMBL392 |
0.82 µM [IC50] | ||
Target ID: CHEMBL352 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Beauvericin: chemical and biological aspects and occurrence]. | 2005 Dec |
|
| Distribution of gibberellin biosynthetic genes and gibberellin production in the Gibberella fujikuroi species complex. | 2005 Jun |
|
| Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+. | 2005 May |
|
| Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum. | 2007 Feb |
|
| Lipid peroxidation and glutathione levels in porcine kidney PK15 cells after individual and combined treatment with fumonisin B(1), beauvericin and ochratoxin A. | 2007 Mar |
|
| PCR approach based on the esyn1 gene for the detection of potential enniatin-producing Fusarium species. | 2007 May 30 |
|
| Fusarium avenaceum -- the North European situation. | 2007 Oct 20 |
|
| Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159. | 2007 Sep |
|
| Complex etiology, prophylaxis and hygiene control in mycotoxic nephropathies in farm animals and humans. | 2008 Apr |
|
| Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. | 2008 Jan |
|
| Statistical optimization of growth medium for the production of the entomopathogenic and phytotoxic cyclic depsipeptide beauvericin from Fusarium oxysporum KFCC 11363P. | 2008 Jan |
|
| Cytotoxicities of enniatins H, I, and MK1688 from Fusarium oxysporum KFCC 11363P. | 2008 Jun 1 |
|
| Diversity in Beauvericin and Enniatins H, I, and MK1688 by Fusarium oxysporum isolated from potato. | 2008 Mar 20 |
|
| Biosynthesis of the cyclooligomer depsipeptide beauvericin, a virulence factor of the entomopathogenic fungus Beauveria bassiana. | 2008 Sep 22 |
|
| Structural analysis of enniatin H, I, and MK1688 and beauvericin by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and their production by Fusarium oxysporum KFCC 11363P. | 2009 Apr |
|
| Beauvericin decreases cell viability of wheat. | 2009 Aug |
|
| Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase. | 2009 Dec |
|
| A beauvericin hot spot in the genus Isaria. | 2009 Dec |
|
| Reactive oxygen species induced by beauvericin, patulin and zearalenone in CHO-K1 cells. | 2009 Dec |
|
| An overview of conventional and emerging analytical methods for the determination of mycotoxins. | 2009 Jan |
|
| Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. | 2009 Jan |
|
| Combinatorial mutasynthesis of scrambled beauvericins, cyclooligomer depsipeptide cell migration inhibitors from Beauveria bassiana. | 2009 Jan 26 |
|
| Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin. | 2009 Jul |
|
| LC-MS/MS multi-analyte method for mycotoxin determination in food supplements. | 2009 Jun |
|
| Dominance of Group 2 and fusaproliferin production by Fusarium subglutinans from Iowa maize. | 2009 Mar |
|
| Biosynthesis of the cyclooligomer depsipeptide bassianolide, an insecticidal virulence factor of Beauveria bassiana. | 2009 May |
|
| Overview of analytical methods for beauvericin and fusaproliferin in food matrices. | 2009 Nov |
|
| Cytotoxic and antibacterial activities of endophytic fungi isolated from plants at the National Park, Pahang, Malaysia. | 2009 Nov 21 |
|
| The nuclear protein Sge1 of Fusarium oxysporum is required for parasitic growth. | 2009 Oct |
|
| Oxidative stress and DNA interactions are not involved in Enniatin- and Beauvericin-mediated apoptosis induction. | 2009 Sep |
|
| Real and perceived risks for mycotoxin contamination in foods and feeds: challenges for food safety control. | 2010 Apr |
|
| Beauvericin and ochratoxin A genotoxicity evaluated using the alkaline comet assay: single and combined genotoxic action. | 2010 Aug |
|
| Antineoplastic activities of MT81 and its structural analogue in Ehrlich ascites carcinoma-bearing Swiss Albino mice. | 2010 Jan-Feb |
|
| «Suspects» in etiology of endemic nephropathy: aristolochic acid versus mycotoxins. | 2010 Jun |
|
| Oligonucleotide microarray for the identification of potential mycotoxigenic fungi. | 2010 Mar 23 |
|
| Nematicidal activity of beauvericin produced by the fungus Fusarium bulbicola. | 2010 Mar-Apr |
|
| Beauvericin from the endophytic fungus, Fusarium redolens, isolated from Dioscorea zingiberensis and its antibacterial activity. | 2010 May |
|
| Formation of fumonisins and other secondary metabolites by Fusarium oxysporum and F. proliferatum: a comparative study. | 2010 May |
|
| Identification, mycotoxin risk and pathogenicity of Fusarium species associated with fig endosepsis in Apulia, Italy. | 2010 May |
|
| Contamination by moulds of grape berries in Slovakia. | 2010 May |
|
| Further data on the presence of Fusarium emerging mycotoxins enniatins, fusaproliferin and beauvericin in cereals available on the Spanish markets. | 2010 May |
|
| Trichothecene and beauvericin mycotoxin production and genetic variability in Fusarium poae isolated from wheat kernels from northern Italy. | 2010 May |
|
| Verrucisidinol and verrucosidinol acetate, two pyrone-type polyketides isolated from a marine derived fungus, Penicillium aurantiogriseum. | 2010 Nov 1 |
|
| Evaluation of beauvericin genotoxicity with the chromosomal aberrations, sister-chromatid exchanges and micronucleus assays. | 2010 Oct |
|
| Production and migration of mycotoxins in sweet pepper analyzed by Multimycotoxin LC-MS/MS. | 2010 Oct 13 |
|
| Antibacterial effect of the bioactive compound beauvericin produced by Fusarium proliferatum on solid medium of wheat. | 2010 Sep 1 |
|
| Mycotoxin production of selected Fusarium species at different culture conditions. | 2010 Sep 30 |
|
| The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis. | 2010 Sep 30 |
|
| Disturbance of antioxidant capacity produced by beauvericin in CHO-K1 cells. | 2014 May 2 |
|
| The mycotoxin beauvericin induces apoptotic cell death in H4IIE hepatoma cells accompanied by an inhibition of NF-κB-activity and modulation of MAP-kinases. | 2014 Nov 18 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:16:39 GMT 2023
by
admin
on
Sat Dec 16 02:16:39 GMT 2023
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| Record UNII |
26S048LS2R
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1976
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3000
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DTXSID00891834
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26048-05-5
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3007984
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C004456
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26S048LS2R
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C1011
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BEAUVERICIN
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