Loline | CAS# 25161-91-5 | Insecticidal

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

MedKoo CAT#: 564525

CAS#: 25161-91-5

Description: Loline is a natural insecticidal and deterrent to a broad range of insects, including species in the Hemiptera, Coleoptera, Hymenoptera, Lepidoptera, and Blattodea orders. Loline deters species such as the bird cherry-oat aphid (genus Rhopalosiphum), large milkweed bug (Oncopeltus fasciatus), and American cockroach (Periplaneta americana), thereby protecting the host plant from insect herbivory.

Chemical Structure

Loline

CAS# 25161-91-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 564525
Name: Loline
CAS#: 25161-91-5
Chemical Formula: C8H14N2O
Exact Mass: 154.11
Molecular Weight: 154.213
Elemental Analysis: C, 62.31; H, 9.15; N, 18.17; O, 10.37

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 650	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Loline

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

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:

Product Data:

Product Data

Instruction:

View handling instruction

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.
In vitro activity:	TBD
In vivo activity:	TBD

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
In vitro protocol:	TBD
In vivo protocol:	TBD

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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.

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