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| IUPAC name
(3S,4aR,4bR,5aS,5bS,16bS,18aS,19aS)-5b-Hydroxy-1,1,10,10,12,12,16b,16c-octamethyl-3-(2-methyl-1-propen-1-yl)-1,4a,4b,6,7,7a,9,9a,10,12,12a,16,16b,16c,17,18,18a,19a-octadecahydro-5bH-[2]benzofuro[5,6-e][1,3]dioxino[5,4:2',3']oxireno[4',4a']chromeno[5',6':6,7]indeno[1,2-b]indol-13(8H)-one
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
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| Properties | |
| C42H55NO7 | |
| Molar mass | 685.8886 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lolitrem B is one of many toxins produced by a fungus called Epichloë festucae var. lolii), which grows in Lolium perenne (perennial ryegrass). The fungus is symbiotic with the ryegrass; it doesn't harm the plant, and the toxins it produces kill insects that feed on ryegrass. Lolitrem B is one of these toxins, but it is also harmful to mammals. The shoots and flowers of infected ryegrass have especially high concentrations of lolitrem B, and when livestock eat too much of them, they get perennial ryegrass staggers. At low doses the animals have tremors, and at higher doses they stagger, and at higher yet doses the animals become paralyzed and die. The blood pressure of the animals also goes up. The effect of the lolitrem B comes on slowly and fades out slowly, as it is stored in fat after the ryegrass is eaten. The condition is especially common in New Zealand and Australia, and plant breeders there have been trying to develop strains of fungus that produce toxins only harmful to pests, and not to mammals.
Lolitrem B affects a kind of ion channel called BK channels. These channels normally open temporarily to allow neurons and other electrically sensitive cells, like some heart cells, to "reset" after they fire; lolitrem B blocks them, preventing the neuron or heart cell from firing again. This affects nerve and heart function. The channel is also involved in blood vessel relaxation, and blocking the channel causes blood vessels to constrict, raising blood pressure.