Butenolide
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| Category | Mycotoxins |
| Catalog number | BBF-03518 |
| CAS | 16275-44-8 |
| Molecular Weight | 141.12 |
| Molecular Formula | C6H7NO3 |
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Description
Butenolide is a mycotoxin produced by Fusarium equisett, F. graminearum and F. tricinctum. It has anti-bacterial, anti-fungal and skin irritation effects. Prolonged exposure can cause skin necrosis.
Specification
| IUPAC Name | N-(5-oxo-2H-furan-2-yl)acetamide |
| Canonical SMILES | CC(=O)NC1C=CC(=O)O1 |
| InChI | InChI=1S/C6H7NO3/c1-4(8)7-5-2-3-6(9)10-5/h2-3,5H,1H3,(H,7,8) |
| InChI Key | HUSDLVGPEKVWAL-UHFFFAOYSA-N |
| Source | Butenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 471.7±44.0°C at 760 mmHg |
| Melting Point | 116-118°C |
| Density | 1.3±0.1 g/cm3 |
Toxicity
| Carcinogenicity | Not listed by IARC. |
| Mechanism Of Toxicity | Butenolide causes lipid peroxidation, disrupting the membrane lipid bilayer and causing damage to membrane protiens. It also induces production of reactive oxygen species by impairing the activities of complexes I-IV of the mitochondrial respiratory chain, especially in the liver, leading to oxidative stress. In addition, butenolide disrupts the cation gradient by inhibiting the activity of Ca2+/Mg2+-ATPase and Na+/K+-ATPase, likely either as a side effect of lipid peroxidation or by binding to the sulfhydryl groups in the active sites of these enzymes. |
| Toxicity | LD50: 44 mg/kg (Intraperitoneal, Mouse); LD50: 275 mg/kg (Oral, Mouse). |
Reference Reading
1. Acylated sucroses and butenolide analog from the leaves of Tripterygium wilfordii Hook. f. and their potential anti-tyrosinase effects
Yun-Fei Ai, Shu-Hui Dong, Bin Lin, Xiao-Xiao Huang, Shao-Jiang Song Fitoterapia. 2022 Sep;161:105250. doi: 10.1016/j.fitote.2022.105250. Epub 2022 Jul 4.
Three undescribed acylated sucroses (1-3), one undescribed butenolide analog (4) along with three known compounds (5-7) were isolated from the aqueous EtOH extract of the dried leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of spectroscopic analyses, electron circular dichroism (ECD) techniques, and saccharide hydrolysis. All the isolated compounds were tested for their anti-tyrosinase effects. Among them, 6 exhibited similar inhibitory effects on tyrosinase with IC50 values of 0.073 mM comparing to arbutin. Additionally, the possible mechanism of the interaction between 6 and the active site of tyrosinase was explored by molecular docking.
2. Synthesis and Antifungal Activity of New butenolide Containing Methoxyacrylate Scaffold
Qian Zhang, Yihao Li, Bin Zhao, Leichuan Xu, Haoyun Ma, Mingan Wang Molecules. 2022 Oct 3;27(19):6541. doi: 10.3390/molecules27196541.
In order to improve the antifungal activity of new butenolides containing oxime ether moiety, a series of new butenolide compounds containing methoxyacrylate scaffold were designed and synthesized, based on the previous reports. Their structures were characterized by 1H NMR, 13C NMR, HR-MS spectra, and X-ray diffraction analysis. The in vitro antifungal activities were evaluated by the mycelium growth rate method. The results showed that the inhibitory activities of these new compounds against Sclerotinia sclerotiorum were significantly improved, in comparison with that of the lead compound 3-8; the EC50 values of V-6 and VI-7 against S. sclerotiorum were 1.51 and 1.81 mg/L, nearly seven times that of 3-8 (EC50 10.62 mg/L). Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compound VI-3 had a significant impact on the structure and function of the hyphal cell of S. sclerotiorum mycelium and the positive control trifloxystrobin. Molecular simulation docking results indicated that the introduction of methoxyacrylate scaffold is beneficial to improving the antifungal activity of these compounds against S. sclerotiorum, which can be used as the lead for further structure optimization.
3. A butenolide signaling system synergized with biosynthetic gene modules led to effective activation and enhancement of silent oviedomycin production in Streptomyces
Junyue Li, Wenxi Wang, Xiang Liu, Yuqing Tian, Huarong Tan, Jihui Zhang Metab Eng. 2022 Jul;72:289-296. doi: 10.1016/j.ymben.2022.04.002. Epub 2022 Apr 18.
Secondary metabolic gene clusters widely exist in the genomes of Streptomyces but mostly remain silent. To awaken this hidden reservoir of natural products, various strategies concerning secondary metabolic pathways are applied. Here, we describe that butenolide signaling molecule deficiency and glucose addition can interdependently activate the expression of silent oviedomycin biosynthetic gene clusters in Streptomyces ansochromogenes and Streptomyces antibioticus. Since oviedomycin is a promising anti-tumor lead compound, in order to improve its yield, we use the cluster-situated genes (ovmF, ovmG, ovmI and ovmH) encoding the enzymes for acyl carrier protein modification and precursor biosynthesis, and the discrete precursor biosynthetic genes (pyk2, gap1 and accA2) involved in glycolysis to assemble two gene modules (pFGIH and pPGA). Their co-overexpression in ΔsabA (a disruption mutant of sabA encoding SAB synthase) has superimposed effect on the yield of oviedomycin, which can be further increased to 59-fold in the presence of galactose as optimal carbon source. This is the most unambiguous evidence that butenolide signaling system can synergize with the optimization of primary metabolism to regulate the expression of secondary metabolic gene clusters, providing efficient strategies for mining natural products of Streptomyces.
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
Mass Spectrum (Electron Ionization)
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
