Loline

By 1950 a reforming process was introduced using a catalyst to improve the yield loline components while minimizing the formation of unwanted material. In catalytic as in thermal reforming, a naphtha-type material serves as the feedstock, but the reactions are carried out in the presence of... 

Lolin Y Chronic neurological toxicity associated with exposure to volatile substances. Hum Toxicol 8 293-300, 1989... 

Lolin Y, O Gorman P. 1988. An intra-erythrocytic low molecular weight lead-binding protein in acute and chronic lead exposure and its possible protective role in lead toxicity. Ann Clin Biochem 25 688-697. 

An intermediate 5-hydroxy-5,6-dihydro-2/7-pyrrolo[l,2- ][l,2]oxazin-7(4a//)-one 142 has been described in the total synthesis of (—)-loline, a pyrrolizidine alkaloid extracted from rye grass Lolium cuneatum. The key step of the synthesis was an intramolecular cycloaddition of acylnitrosodienes (obtained by in situ oxidation of the corresponding hydroxamic acids 143). This reaction generated predominantly the rro/o-stereoisomer that was further cleaved at the N-O bond with Na(Hg) and further elaborated in several steps to reach the target compound (Scheme 19) <2001J(P 1)1831 >. 

Tong DW et al, Seasonal change of loline alkaloids in endophyte-infected meadow fescue, Agric Sci China 5 793-797, 2006. 

Spiering MJ et al. Gene clusters for insecticidal loline alkaloids in the grass-endophytic fungus Neotyphodium uncinatum, Genetics 169 1403—1414, 2005. 

Fused ring products also may be formed from the transannular cyclization of medium ring unsaturated amine derivatives, as shown in Table 27.218 A transannular cyclization to the loline ring system was reported by Wilson (entry 4).218c Cyclization of a tertiary amine to a pyrrolizidine perchlorate has also been reported.219... 

The simple necine bases loline (18), norloline (19), and lolinine (20) have been identified previously from Lolium cuneatum Nevski.7 Further investigations on the seeds of this plant by Russian workers have established the presence of four new alkaloids. N-Formylnorloline (21),8 JV-methyl-loline (22), JV-acetylnorloline (23), and AT-formyl-loline (24)9 have been identified. In addition, a novel dimeric pyrrolizidine alkaloid, lolidine, containing chlorine, was isolated in trace amounts (7 mg from 10 kg of seeds). The structure (25) has been suggested for lolidine on the basis of spectral data.10... 

The bases (46) and (47), derived from the loline group of alkaloids, have been used as stimulants of plant growth.40... 

Norditerpene Loline Pyrrolizidine Delphinium occidentale Lolium temulentum Castilleja sulphurea Rhinanthus minor... 

A number of closely related naturally occurring pyrrolizidine cyclic ethers have been identified. Four of these, loline ( = festucine ) (119), norloline... 

The structure (25) has been deduced for both loline, an alkaloid of Lolium cuneatum Nevski, ° and festucine, a constituent of Festuca arundinacea Schreb. The identity of loline and festucine has now been confirmed by direct comparison. 

Blankenship JD, Spiering MJ, Wilkinson UH, Fannin FF, Bush LP, Schardl CL. Production of loline alkaloids by the grass endophyte, Neotyphodium uncinatum, in defined media. Phytochemistry 58 395-401, 2001. 

TePaske MR, Powell RG, Clement SL. Analyses of selected endophyte-infected grasses for the presence of loline-type and ergot-type alkaloids. J Agric Food Chem 41 2299-2303, 1993. 

Wilkinson HH, Siegel MR, Blankenship JD, Mallory AC, Bush LP, Schardl CL. Contribution of fungal loline alkaloids to protection from aphids in a grass-endophyte mutualism. Mol Plant-Microbe Int 13 1027-1033, 2000. 

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