Beauvericin
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Beauvericin

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Beauvericin is produced by the strain of Streptomyces sp. Ba cyclic depsipeptide isolated from several fungal genera, notably beauveria and fusarium; exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities; exhibits ionophoric properties, and inhibits acyl-coa:Cholesterol acyltransferase activity; induces apoptosis by elevating intracellular calcium levels.

Category
Peptide Inhibitors
Catalog number
BAT-015798
CAS number
26048-05-5
Molecular Formula
C45H57N3O9
Molecular Weight
783.95
Beauvericin
IUPAC Name
(3S,6R,9S,12R,15S,18R)-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-hexone
Synonyms
Cyclo(-D-alpha-hydroxyisovaleryl-N-Me-Phe)3
Appearance
White Powder
Purity
>97% by HPLC
Density
1.13 g/cm3
Melting Point
93-94 °C
Boiling Point
975.6°C at 760 mmHg
Storage
-20°C
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.
InChI
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
InChI Key
GYSCAQFHASJXRS-FFCOJMSVSA-N
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
1. In vitro mechanisms of Beauvericin toxicity: A review
Alessandra Prosperini, Beatriz Mallebrera, María José Ruiz, Guillermina Font Food Chem Toxicol . 2018 Jan;111:537-545. doi: 10.1016/j.fct.2017.11.019.
Beauvericin (BEA) is a mycotoxin produced by many species of fungus Fusarium and by Beauveria bassiana; BEA is a natural contaminant of cereals and cereals based products and possesses a wide variety of biological properties. The mechanism of action seems to be related to its ionophoric activity, that increases ion permeability in biological membranes. As a consequence, BEA causes cytotoxicity in several cell lines and is capable to produce oxidative stress at molecular level. Moreover, BEA is genotoxic (produces DNA fragmentation, chromosomal aberrations and micronucleus) and causes apoptosis with the involvement of mitochondrial pathway. However, several antioxidant mechanisms protect cells against oxidative stress produced by BEA. Despite its strong cytotoxicity, no risk assessment have been still carried out by authorities due to a lack of toxicity data, so research on BEA toxicological impact is still going on. This review reports information available regarding BEA mechanistic toxicology with the aim of updating information regarding last researches on this mycotoxin.
2. Mycotoxins: occurrence, toxicology, and exposure assessment
A J Ramos, S Marin, V Sanchis, G Cano-Sancho Food Chem Toxicol . 2013 Oct;60:218-37. doi: 10.1016/j.fct.2013.07.047.
Mycotoxins are abiotic hazards produced by certain fungi that can grow on a variety of crops. Consequently, their prevalence in plant raw materials may be relatively high. The concentration of mycotoxins in finished products is usually lower than in raw materials. In this review, occurrence and toxicology of the main mycotoxins are summarised. Furthermore, methodological approaches for exposure assessment are described. Existing exposure assessments, both through contamination and consumption data and biomarkers of exposure, for the main mycotoxins are also discussed.
3. Beauvericin, a bioactive compound produced by fungi: a short review
Lijian Xu, Qinggui Wang Molecules . 2012 Feb 24;17(3):2367-77. doi: 10.3390/molecules17032367.
Beauvericin is a cyclic hexadepsipeptide mycotoxin, which has insecticidal, antimicrobial, antiviral and cytotoxic activities. It is a potential agent for pesticides and medicines. This paper reviews the bioactivity, fermentation and biosynthesis of the fungal product beauvericin.
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