Beauvericin
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| Category | Antibiotics |
| Catalog number | BBF-00628 |
| CAS | 26048-05-5 |
| Molecular Weight | 783.95 |
| Molecular Formula | C45H57N3O9 |
| Purity | >97% by HPLC |
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Description
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.
Specification
| Synonyms | Cyclo(-D-alpha-hydroxyisovaleryl-N-Me-Phe)3 |
| Storage | -20°C |
| 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 |
| 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 |
| 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 |
| Source | Beauvericin was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species. |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | parasites; fungi |
| Boiling Point | 975.6°C at 760 mmHg |
| Melting Point | 93-94 °C |
| Density | 1.13 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Toxicity
| Carcinogenicity | Not listed by IARC. |
| Mechanism Of Toxicity | Beauvericin is cytotoxic and increases ion permeability in cell membranes by forming complexes with essential cations (Ca2+, Na+, K+) and by forming cation-selective channels in lipid membranes. This may affect ionic homeostasis, increasing the intracellular calcium concentration, and lead to apoptosis. Beauvericin is also genotoxic and causes DNA damage, either by directly forming DNA adducts, through increased intracellular calcium levels influencing endonuclease activity, or through oxidative stress. Beauvericin induces lipid peroxidation and production of reactive oxygen species, producing cytotoxic effects and immunosuppressive activity. In addition, beauvericin is a potent inhibitor of the acyl-CoA:cholesterol acyltransferase (ACAT), which plays an important role in cholesterol ester accumulation in atherogenesis and in cholesterol absorption from the intestine. In isolated terminal ilea and heart muscles of guinea pig, beauvericin decreases the contractility, shortening the action potential duration and depolarizing the membrane resting potential. Beauvericin is also known to inhibit certain cytochrome P-450 enzymes. |
Reference Reading
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.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
