Record Information |
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Version | 2.0 |
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Creation Date | 2010-05-20 16:06:57 UTC |
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Update Date | 2014-12-24 20:26:31 UTC |
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Accession Number | T3D3767 |
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Identification |
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Common Name | Lolitrem B |
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Class | Small Molecule |
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Description | Paspalinine is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes" or “ryegrass staggers”. (5, 1, 3) |
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Compound Type | - Ester
- Ether
- Fungal Toxin
- Mycotoxin
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | |
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Chemical Formula | C42H55NO7 |
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Average Molecular Mass | 685.889 g/mol |
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Monoisotopic Mass | 685.398 g/mol |
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CAS Registry Number | 81771-19-9 |
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IUPAC Name | 22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-en-1-yl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.0²,¹⁷.0⁴,¹⁶.0⁷,¹⁵.0⁹,¹³.0²²,³⁶.0²³,²⁵.0²³,³³.0²⁶,³¹]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one |
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Traditional Name | 22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-en-1-yl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.0²,¹⁷.0⁴,¹⁶.0⁷,¹⁵.0⁹,¹³.0²²,³⁶.0²³,²⁵.0²³,³³.0²⁶,³¹]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one |
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SMILES | CC(C)=CC1OC2C3OC33C(CCC4(C)C5(C)C(CC6=C5NC5=C6C6=C(C=C5)C(=O)C5C(C6)C(C)(C)OC5(C)C)CCC34O)OC2C(C)(C)O1 |
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InChI Identifier | InChI=1S/C42H55NO7/c1-20(2)17-28-47-32-34(38(7,8)48-28)46-27-14-15-39(9)40(10)21(13-16-41(39,45)42(27)35(32)49-42)18-24-29-23-19-25-30(37(5,6)50-36(25,3)4)31(44)22(23)11-12-26(29)43-33(24)40/h11-12,17,21,25,27-28,30,32,34-35,43,45H,13-16,18-19H2,1-10H3 |
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InChI Key | InChIKey=HGBZMCXKHKZYBF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Not Available |
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Direct Parent | Naphthopyrans |
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Alternative Parents | |
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Substituents | - Naphthopyran
- Naphthofuran
- Naphthalene
- Tetralin
- 3-alkylindole
- Indole
- Indole or derivatives
- Aryl alkyl ketone
- Aryl ketone
- 1,4-dioxepane
- Dioxepane
- Meta-dioxane
- Monosaccharide
- Oxane
- Pyran
- Benzenoid
- Cyclic alcohol
- Pyrrole
- Tertiary alcohol
- Tetrahydrofuran
- Heteroaromatic compound
- Ketone
- Acetal
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Azacycle
- Organic nitrogen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-1000019000-66132e6b0615956284e7 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004l-7500059000-911c3fa783cecc676d27 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-066r-9000161000-cc41dc0c2503d27116db | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000019000-435251defe06ce871327 | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0uyi-3100059000-7d2634584c9c4489b12d | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0apl-9300052000-5c3596e8eb34d48ec6cc | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000009000-9ac32f594a0080abf166 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fri-2000019000-8744ed0236dca05eac59 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000f-9110035000-9bae12f1443f21c69d37 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000009000-dd2f6c392bd7721a00f1 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0000009000-e9e00ac78c08bd2e0a36 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-1120119000-9011ab8bd05cd587d4e7 | 2021-10-12 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (4) |
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Mechanism of Toxicity | The neurological effects of Lolitrem B are a result of its ability to inhibit large conductance calcium-activated potassium channels (BK channels). Lolitrem B binds to the alpha subunit of the BK channel, inhibiting channel potassium currents. This causes tremorgenic effects either by directly affecting channels in the muscle or by acting on channels in the central nervous system. (1, 2) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Lolitrem B is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (5, 1, 3) |
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Minimum Risk Level | Symptoms of "ryegrass staggers" develop in livestock when concentrations exceed 2.5 ug/g in dry matter. (3) |
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Health Effects | Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome" or “ryegrass staggers”. (5, 1) |
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Symptoms | Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome" or “ryegrass staggers”, which is characterized by impaired motor coordination, muscle tremors, hyperexcitability, convulsions, and ataxia. Additional symptoms include increased blood pressure, heart rate and respiration rate. While the neurotoxic effects of lolitrem B have a long duration, they are also reversible. (5, 1, 2, 3) |
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Treatment | To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (6) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 3086140 |
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ChEMBL ID | Not Available |
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ChemSpider ID | Not Available |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | Not Available |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | - Imlach WL, Finch SC, Dunlop J, Meredith AL, Aldrich RW, Dalziel JE: The molecular mechanism of "ryegrass staggers," a neurological disorder of K+ channels. J Pharmacol Exp Ther. 2008 Dec;327(3):657-64. doi: 10.1124/jpet.108.143933. Epub 2008 Sep 18. [18801945 ]
- Dalziel JE, Finch SC, Dunlop J: The fungal neurotoxin lolitrem B inhibits the function of human large conductance calcium-activated potassium channels. Toxicol Lett. 2005 Mar 15;155(3):421-6. [15649626 ]
- Cheeke PR: Endogenous toxins and mycotoxins in forage grasses and their effects on livestock. J Anim Sci. 1995 Mar;73(3):909-18. [7608026 ]
- Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- Selala MI, Daelemans F, Schepens PJ: Fungal tremorgens: the mechanism of action of single nitrogen containing toxins--a hypothesis. Drug Chem Toxicol. 1989 Sep-Dec;12(3-4):237-57. [2698801 ]
- Schell MM. Tremorgenic mycotoxin intoxication. Veterinary Medicine. 2000.
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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