Butenolide
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Basic Info
| Common Name | Butenolide(F04997) |
| 2D Structure | |
| Description | Butenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. Butenolide had been implicated as the causative agent of a livestock mycotoxicosis called “fescue foot”, a peripheral vascular disorder occurring in cattle grazing on tall fescue grass. Butenolide is also one of the mycotoxins which have been considered as a suspected etiological factor for Kaschin-Beck disease (an endemic osteoarthropathy) and Keshan disease (an endemic cardiomyopathy), prevailing in some regions of China, and several studies have also indicated that butenolide can cause cartilage damage. (A3036, A3039) |
| FRCD ID | F04997 |
| CAS Number | 16275-44-8 |
| PubChem CID | 27790 |
| Formula | C6H7NO3 |
| IUPAC Name | N-(5-oxo-2H-furan-2-yl)acetamide |
| InChI Key | HUSDLVGPEKVWAL-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H7NO3/c1-4(8)7-5-2-3-6(9)10-5/h2-3,5H,1H3,(H,7,8) |
| Canonical SMILES | CC(=O)NC1C=CC(=O)O1 |
| Isomeric SMILES | CC(=O)NC1C=CC(=O)O1 |
| Wikipedia | Butenolide |
| Synonyms |
5-Acetamido-2(5)-furanone
2(5H)-Furanone, 5-acetamido-
N-(5-oxo-2H-furan-2-yl)acetamide
16275-44-8
ACETAMIDE, N-(2,5-DIHYDRO-5-OXO-2-FURANYL)-
Acetamide, N-(2,5-dihydro-5-oxo-2-furyl)-
NSC 114350
BRN 1680823
AI3-44725
4-Acetamido-4-hydroxy-2-butenoic acid gamma-lactone
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Dihydrofurans |
| Subclass | Furanones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Butenolides |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | 2-furanone - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Lactone - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Oxacycle - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 141.126 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 197 |
| Monoisotopic Mass | 141.043 |
| Exact Mass | 141.043 |
| XLogP | -0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9888 |
| Human Intestinal Absorption | HIA+ | 0.9908 |
| Caco-2 Permeability | Caco2- | 0.5143 |
| P-glycoprotein Substrate | Non-substrate | 0.8936 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9069 |
| Non-inhibitor | 0.9724 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9437 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5897 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6933 |
| CYP450 2D6 Substrate | Non-substrate | 0.8287 |
| CYP450 3A4 Substrate | Non-substrate | 0.6699 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8936 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9337 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9377 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9445 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9753 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9764 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9861 |
| Non-inhibitor | 0.9915 | |
| AMES Toxicity | Non AMES toxic | 0.7429 |
| Carcinogens | Non-carcinogens | 0.8508 |
| Fish Toxicity | High FHMT | 0.7040 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6022 |
| Honey Bee Toxicity | Low HBT | 0.5380 |
| Biodegradation | Ready biodegradable | 0.8582 |
| Acute Oral Toxicity | III | 0.6273 |
| Carcinogenicity (Three-class) | Non-required | 0.4515 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2255 | LogS |
| Caco-2 Permeability | 0.9858 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0027 | LD50, mol/kg |
| Fish Toxicity | 1.8216 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.7192 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Impact of glutathione modulation on the toxicity of the Fusarium mycotoxins deoxynivalenol (DON), NX-3 and butenolide in human liver cells. | Toxicol Lett | 2018 Sep 20 | 30244016 |
| Causal agents of Fusarium head blight of durum wheat (Triticum durum Desf.) in central Italy and their in vitro biosynthesis of secondary metabolites. | Food Microbiol | 2018 Apr | 29173624 |
| Emerging Mycotoxins: Beyond Traditionally Determined Food Contaminants. | J Agric Food Chem | 2017 Aug 23 | 27599910 |
| Role of the European corn borer (Ostrinia nubilalis) on contamination of maize with 13 Fusarium mycotoxins. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 25266165 |
| Study of embryotoxicity of Fusarium mycotoxin butenolide using a whole rat embryo culture model. | Toxicol In Vitro | 2011 Dec | 21945046 |
| Genotoxicity evaluation of two kinds of smoke-water and 3,7-dimethyl-2H-furo[2,3-c]pyran-2-one. | J Appl Toxicol | 2010 Aug | 20809549 |
| Repeated administration of a Fusarium mycotoxin butenolide to rats induces hepatic lipid peroxidation and antioxidant defense impairment. | Food Chem Toxicol | 2009 Mar | 19150382 |
| Molecular biology of Fusarium mycotoxins. | Int J Food Microbiol | 2007 Oct 20 | 17707105 |
| Dermal toxicity of Fusarium toxins in combinations. | Arch Toxicol | 1988 Jan | 3355369 |
| Simultaneous detection of several Fusarium mycotoxins in cereals, grains, and foodstuffs. | J Assoc Off Anal Chem | 1981 Sep | 7287603 |
| Mouse bioassay for Fusarium metabolites: rejection or acceptance when dissolved in drinking water. | Appl Environ Microbiol | 1980 May | 7396486 |
| Toxic effects of a butenolide mycotoxin and of Fusarium tricinctum cultures in cattle. | J Am Vet Med Assoc | 1972 Jun 1 | 5027735 |
| Correlation of biological to chromatographic data for two mycotoxins elaborated by Fusarium. | Appl Microbiol | 1971 Apr | 5575569 |
| Biological assays for two mycotoxins produced by Fusarium tricinctum. | Appl Microbiol | 1970 Sep | 5485724 |
Targets
- General Function:
- Pdz domain binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
- Gene Name:
- ATP2B1
- Uniprot ID:
- P20020
- Molecular Weight:
- 138754.045 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Metal ion binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium.
- Gene Name:
- ATP2C2
- Uniprot ID:
- O75185
- Molecular Weight:
- 103186.475 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Signal transducer activity
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium.
- Gene Name:
- ATP2C1
- Uniprot ID:
- P98194
- Molecular Weight:
- 100576.42 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- S100 protein binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Isoform 2 is involved in the regulation of the contraction/relaxation cycle.
- Gene Name:
- ATP2A2
- Uniprot ID:
- P16615
- Molecular Weight:
- 114755.765 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Metal ion binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium. Transports calcium ions from the cytosol into the sarcoplasmic/endoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
- Gene Name:
- ATP2A3
- Uniprot ID:
- Q93084
- Molecular Weight:
- 113976.23 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A1
- Uniprot ID:
- P05023
- Molecular Weight:
- 112895.01 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A2
- Uniprot ID:
- P50993
- Molecular Weight:
- 112264.385 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A3
- Uniprot ID:
- P13637
- Molecular Weight:
- 111747.51 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
- Gene Name:
- ATP1B2
- Uniprot ID:
- P14415
- Molecular Weight:
- 33366.925 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
- Gene Name:
- ATP1B3
- Uniprot ID:
- P54709
- Molecular Weight:
- 31512.34 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Transporter activity
- Specific Function:
- May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
- Gene Name:
- FXYD2
- Uniprot ID:
- P54710
- Molecular Weight:
- 7283.265 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Protein c-terminus binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
- Gene Name:
- ATP2B2
- Uniprot ID:
- Q01814
- Molecular Weight:
- 136875.18 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Pdz domain binding
- Specific Function:
- This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
- Gene Name:
- ATP2B3
- Uniprot ID:
- Q16720
- Molecular Weight:
- 134196.025 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Scaffold protein binding
- Specific Function:
- Calcium/calmodulin-regulated and magnesium-dependent enzyme that catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell (PubMed:8530416). By regulating sperm cell calcium homeostasis, may play a role in sperm motility (By similarity).
- Gene Name:
- ATP2B4
- Uniprot ID:
- P23634
- Molecular Weight:
- 137919.03 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Key regulator of striated muscle performance by acting as the major Ca(2+) ATPase responsible for the reuptake of cytosolic Ca(2+) into the sarcoplasmic reticulum. Catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
- Gene Name:
- ATP2A1
- Uniprot ID:
- O14983
- Molecular Weight:
- 110251.36 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
- Gene Name:
- ATP1A4
- Uniprot ID:
- Q13733
- Molecular Weight:
- 114165.44 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
- Gene Name:
- ATP1B1
- Uniprot ID:
- P05026
- Molecular Weight:
- 35061.07 Da
- Mechanism of Action:
- 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.
References
- Wang YM, Peng SQ, Zhou Q, Wang MW, Yan CH, Wang GQ, Yang HY: The oxidative damage of butenolide to isolated erythrocyte membranes. Toxicol In Vitro. 2007 Aug;21(5):863-9. Epub 2007 Feb 28. [17416482 ]