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MedKoo Cat#: 599165 | Name: Lolitrem B

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lolitrem B is one of many toxins produced by a fungus called Epichloë festucae (var. lolii), which grows in 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.

Chemical Structure

Lolitrem B
Lolitrem B
CAS#81771-19-9

Theoretical Analysis

MedKoo Cat#: 599165

Name: Lolitrem B

CAS#: 81771-19-9

Chemical Formula: C42H55NO7

Exact Mass: 685.3979

Molecular Weight: 685.90

Elemental Analysis: C, 73.55; H, 8.08; N, 2.04; O, 16.33

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Lolitrem B;
IUPAC/Chemical Name
(3S,4aR,4bR,5aS,5bS,16bS,18aS,19aS)-5b-hydroxy-1,1,10,10,12,12,16b,16c-octamethyl-3-(2-methylprop-1-en-1-yl)-1,4a,4b,5b,6,7a,9,9a,10,12,12a,16,16b,16c,17,18,18a,19a-octadecahydro-7H-[1,3]dioxino[5'',4'':2',3']oxireno[2'',3'':4',4a']chromeno[5',6':6,7]indeno[1,2-b]isobenzofuro[5,6-e]indol-13(8H)-one
InChi Key
HGBZMCXKHKZYBF-LIHFUKCQSA-N
InChi Code
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/t21?,25?,27-,28-,30?,32+,34-,35+,39?,40+,41-,42-/m0/s1
SMILES Code
C/C(C)=C/[C@H]1O[C@H]2[C@@H]3[C@]4([C@@H](O[C@@H]2C(C)(C)O1)CCC5(C)[C@@]4(O)CCC6[C@]5(C)c7[nH]c8ccc9c(CC%10C(C(C)(C)OC%10(C)C)C9=O)c8c7C6)O3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 685.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Repussard C, Zbib N, Tardieu D, Guerre P. Ergovaline and lolitrem B concentrations in perennial ryegrass in field culture in southern France: distribution in the plant and impact of climatic factors. J Agric Food Chem. 2014 Dec 31;62(52):12707-12. doi: 10.1021/jf504581y. Epub 2014 Dec 19. PubMed PMID: 25526521. 2: Johnstone LK, Mayhew IG. Flow-mediated K(+) secretion in horses intoxicated with lolitrem B (perennial ryegrass staggers). N Z Vet J. 2013 May;61(3):159-64. doi: 10.1080/00480169.2012.731682. Epub 2012 Nov 8. PubMed PMID: 23134178. 3: Shimada N, Yoshioka M, Mikami O, Tanimura N, Yamanaka N, Hanazumi M, Kojima F, Miyazaki S. Toxicological evaluation and bioaccumulation potential of lolitrem B, endophyte mycotoxin in Japanese black steers. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(8):1402-6. doi: 10.1080/19440049.2013.790090. Epub 2013 May 31. PubMed PMID: 23721156. 4: Johnstone LK, Mayhew IG, Fletcher LR. Clinical expression of lolitrem B (perennial ryegrass) intoxication in horses. Equine Vet J. 2012 May;44(3):304-9. doi: 10.1111/j.2042-3306.2011.00439.x. Epub 2011 Jul 27. PubMed PMID: 21793878. 5: Philippe G. Lolitrem B and Indole Diterpene Alkaloids Produced by Endophytic Fungi of the Genus Epichloë and Their Toxic Effects in Livestock. Toxins (Basel). 2016 Feb 15;8(2):47. doi: 10.3390/toxins8020047. Review. PubMed PMID: 26891327; PubMed Central PMCID: PMC4773800. 6: Fuchs B, Krischke M, Mueller MJ, Krauss J. Peramine and lolitrem B from endophyte-grass associations cascade up the food chain. J Chem Ecol. 2013 Dec;39(11-12):1385-9. PubMed PMID: 24233445. 7: Saikia S, Takemoto D, Tapper BA, Lane GA, Fraser K, Scott B. Functional analysis of an indole-diterpene gene cluster for lolitrem B biosynthesis in the grass endosymbiont Epichloë festucae. FEBS Lett. 2012 Jul 30;586(16):2563-9. doi: 10.1016/j.febslet.2012.06.035. Epub 2012 Jun 29. PubMed PMID: 22750140. 8: Imlach WL, Finch SC, Zhang Y, Dunlop J, Dalziel JE. Mechanism of action of lolitrem B, a fungal endophyte derived toxin that inhibits BK large conductance Ca²+-activated K+ channels. Toxicon. 2011 Apr;57(5):686-94. doi: 10.1016/j.toxicon.2011.01.013. Epub 2011 Feb 12. PubMed PMID: 21300077. 9: Miyazaki S, Ishizaki I, Ishizaka M, Kanbara T, Ishiguro-Takeda Y. Lolitrem B residue in fat tissues of cattle consuming endophyte-infected perennial ryegrass straw. J Vet Diagn Invest. 2004 Jul;16(4):340-2. PubMed PMID: 15305749. 10: McLeay LM, Smith BL, Munday-Finch SC. Tremorgenic mycotoxins paxilline, penitrem and lolitrem B, the non-tremorgenic 31-epilolitrem B and electromyographic activity of the reticulum and rumen of sheep. Res Vet Sci. 1999 Apr;66(2):119-27. Erratum in: Res Vet Sci 1999 Dec;67(3):313. PubMed PMID: 10208889. 11: 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. PubMed PMID: 15649626. 12: Finch SC, Thom ER, Babu JV, Hawkes AD, Waugh CD. The evaluation of fungal endophyte toxin residues in milk. N Z Vet J. 2013 Jan;61(1):11-7. doi: 10.1080/00480169.2012.704626. Epub 2012 Sep 18. PubMed PMID: 22984816. 13: Tor-Agbidye J, Blythe LL, Craig AM. Correlation of endophyte toxins (ergovaline and lolitrem B) with clinical disease: fescue foot and perennial ryegrass staggers. Vet Hum Toxicol. 2001 Jun;43(3):140-6. PubMed PMID: 11383653. 14: Smith BL, McLeay LM, Embling PP. Effect of the mycotoxins penitrem, paxilline and lolitrem B on the electromyographic activity of skeletal and gastrointestinal smooth muscle of sheep. Res Vet Sci. 1997 Mar-Apr;62(2):111-6. PubMed PMID: 9243707. 15: Finch SC, Fletcher LR, Babu JV. The evaluation of endophyte toxin residues in sheep fat. N Z Vet J. 2012 Jan;60(1):56-60. doi: 10.1080/00480169.2011.634746. PubMed PMID: 22175431. 16: Hovermale JT, Craig AM. Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne). J Vet Diagn Invest. 2001 Jul;13(4):323-7. PubMed PMID: 11478604. 17: Grancher D, Jaussaud P, Durix A, Berthod A, Fenet B, Moulard Y, Bonnaire Y, Bony S. Countercurrent chromatographic isolation of lolitrem B from endophyte-infected ryegrass (Lolium perenne L.) seed. J Chromatogr A. 2004 Dec 3;1059(1-2):73-81. PubMed PMID: 15628126. 18: Munday BL, Monkhouse IM, Gallagher RT. Intoxication of horses by lolitrem B in ryegrass seed cleanings. Aust Vet J. 1985 Jun;62(6):207. PubMed PMID: 4062734. 19: Gallagher RT, Hawkes AD, Stewart JM. Rapid determination of the neurotoxin lolitrem B in perennial ryegrass by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1985 Mar 8;321(1):217-26. PubMed PMID: 3988840. 20: Prestidge RA, Sprosen JM. The effect of glyphosate, paraquat and paclobutrazol on lolitrem B levels in endophyte-infected perennial ryegrass. N Z Vet J. 1995 Aug;43(4):138-40. PubMed PMID: 16031833.

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Nor-Calcimimetic B

Nor-Calcimimetic B