IUPAC/Chemical Name
(1S,6R,7R,7aS)-N-methylhexahydro-1H-1,6-epoxypyrrolizin-7-amine
InChi Key
OPMNROCQHKJDAQ-FKSUSPILSA-N
InChi Code
InChI=1S/C8H14N2O/c1-9-7-6-4-10-3-2-5(11-6)8(7)10/h5-9H,2-4H2,1H3/t5-,6+,7-,8+/m0/s1
SMILES Code
CN[C@H]1[C@@]2([H])CN3[C@]1([H])[C@](O2)([H])CC3
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
Biological target:
Loline is a natural insecticidal and deterrent to a broad range of insects, including species in the Hemiptera, Coleoptera, Hymenoptera, Lepidoptera, and Blattodea orders.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
154.21
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.
| 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 |
Formulation protocol:
TBD
1: Adhikari KB, Boelt B, Fomsgaard IS. Identification and Quantification of Loline-Type Alkaloids in Endophyte-Infected Grasses by LC-MS/MS. J Agric Food Chem. 2016 Aug 10;64(31):6212-8. doi: 10.1021/acs.jafc.6b02616. Epub 2016 Aug 2. PubMed PMID: 27434508.
2: Finch SC, Munday JS, Munday R, Kerby JW. Short-term toxicity studies of loline alkaloids in mice. Food Chem Toxicol. 2016 Aug;94:243-9. doi: 10.1016/j.fct.2016.06.002. Epub 2016 Jun 6. PubMed PMID: 27276360.
3: Barker GM, Patchett BJ, Cameron NE. Epichloë uncinata Infection and Loline Content Protect Festulolium Grasses From Crickets (Orthoptera: Gryllidae). J Econ Entomol. 2015 Apr;108(2):789-97. doi: 10.1093/jee/tou058. Epub 2015 Feb 4. PubMed PMID: 26470191.
4: Miller KE, Wright AJ, Olesen MK, Hovey MT, Scheerer JR. Stereoselective synthesis of (+)-loline alkaloid skeleton. J Org Chem. 2015 Feb 6;80(3):1569-76. doi: 10.1021/jo502493e. Epub 2015 Jan 22. PubMed PMID: 25611615.
5: Pan J, Bhardwaj M, Nagabhyru P, Grossman RB, Schardl CL. Enzymes from fungal and plant origin required for chemical diversification of insecticidal loline alkaloids in grass-Epichloë symbiota. PLoS One. 2014 Dec 22;9(12):e115590. doi: 10.1371/journal.pone.0115590. eCollection 2014. PubMed PMID: 25531527; PubMed Central PMCID: PMC4274035.
6: Pan J, Bhardwaj M, Faulkner JR, Nagabhyru P, Charlton ND, Higashi RM, Miller AF, Young CA, Grossman RB, Schardl CL. Ether bridge formation in loline alkaloid biosynthesis. Phytochemistry. 2014 Feb;98:60-8. doi: 10.1016/j.phytochem.2013.11.015. Epub 2013 Dec 26. PubMed PMID: 24374065; PubMed Central PMCID: PMC3929955.
7: Roberts E, Lindow S. Loline alkaloid production by fungal endophytes of Fescue species select for particular epiphytic bacterial microflora. ISME J. 2014 Feb;8(2):359-68. doi: 10.1038/ismej.2013.170. Epub 2013 Oct 10. PubMed PMID: 24108329; PubMed Central PMCID: PMC3906823.
8: Gooneratne SR, Patchett BJ, Wellby M, Fletcher LR. Excretion of loline alkaloids in urine and faeces of sheep dosed with meadow fescue (Festuca pratensis) seed containing high concentrations of loline alkaloids. N Z Vet J. 2012 May;60(3):176-82. doi: 10.1080/00480169.2011.644189. PubMed PMID: 22480356.
9: Cakmak M, Mayer P, Trauner D. An efficient synthesis of loline alkaloids. Nat Chem. 2011 Jun 19;3(7):543-5. doi: 10.1038/nchem.1072. PubMed PMID: 21697875.
10: Zhang DX, Nagabhyru P, Blankenship JD, Schardl CL. Are loline alkaloid levels regulated in grass endophytes by gene expression or substrate availability? Plant Signal Behav. 2010 Nov;5(11):1419-22. doi: 10.1104/pp.109.138222. Epub 2010 Nov 1. PubMed PMID: 21051952; PubMed Central PMCID: PMC3115243.
