859. The alkaloids of perennial rye-grass (Lolium perenne L.). Part I. Perloline

Abstract

Perloline is shown to be a normal constituent of perennial rye-grass growing in Britain.Perloline is shown to exist in different solvents as an anhydronium base, a pseudo-base, or an ether thereof, as a cation, or as an anion.IN 1941 Melville and Grimmett reported the presence of a yellow, fluorescent alkaloid in perennial rye-grass (Lolium perenne L.) growing in New Zealand, and called this base Per1oline.l The alkaloids of this grass have formed the subject of a number of Papers dealing with the extraction of perloline and other bases from the grass,2 the estimation of alkaloids in the grass,3 the characterisation and chemistry of perl~line,~ its toxicity and physiological effect^,^ its effect on plant growth,6 and the effect of genetic differences on the perloline content of rye-grass herbage.7 Besides perloline, a colourless fluorescent base has been characterised and called perlolidine; 2 ~p k 8 a volatile base and a red, fluorescent basic fraction have been d e ~c r i b e d , ~J b ~~ the last two not being fully characterised. Surveys of other species of grass grown in New Zealand showed that perloline was also present in Lolium temulentum L., Festuca arundinacea Shreb., and Setaria lutescens (Weigel) F. T. Hubb; it has also been reported in Lolium multiforum Lam., Dactylis glomerata L., and Phleum pratense L.2c94c In Lolium perenne the alkaloid was present chiefly in the stems, and then only in the summer.The writer has detected perloline spectroscopically in an extract from L. $eren?.te growing wild in Leeds during May (but not during the previous December) and isolated it from this grass growing wild at Barnet, Hertfordshire during July, and on a much larger scale from hay from a pure strain of Lolium perenne grown at Auchincruive, Ayrshire, harvested in the early summer. Paper chromatography of the bases from the last two sources showed that there were more alkaloids in the grass than had been previously reported. The chromatogram could be divided into ten zones, one of which is perloline. Preparative chromatography on columns has shown that some of these zones contain more than one base. The overall yield of 490 mg. of perloline from 52 kg. of hay (10 p.p.m., corresponding to about 2 p.p.m. in the grass) is low compared with that reported from New Zealand. Some perloline may have been destroyed in the hay-making (another sample of this grass, dried by hot air, contained traces only of perloline); also, the hay contained basic material which, though not perloline, gave a yellow solution in chloroform, with a green fluorescence. If this material is present in the fresh grass, then the published colorimetric method for estimating perlolineThe workers in New Zealand published analyses for perloline and derivatives, and assigned to the base the formula C4,H,N407 containing 2 basic nitrogen atoms, 4 methoxyl groups, and one acetylateable hydroxyl group. No degradation product of known

Alkaloid toxins in endophyte‐infected grasses

“…1967Kaczmarek et al, 1967 Kaczmarek et al, I967 Powell et al, I990 Karimoto et al, 1964Culvenor. 1973Davis et al, 1983Jeffreys, 1964Yates, 1962Yates, 1962Gallagher et al, 1984 Weedon and Mantle, Rowan et al, 1986Yates et al, 1975Dannhardt and Steindl, Jeffreys, 1970Jeffreys, 1964 aPlant code numbers correspond to grass and associated endophyte listed in Table I (Clement, unpublished data). Further research on the chemistry of these unique Acremonium and Bulunsiu grass-fungal interactions is expected to lead to methods to predict and control animal toxicity, to suggest leads for environmentally safe insect-control agents, and to provide new compounds useful as pharmaceuticals.…”

Factors Affecting the Alkaloid Content of Tall Fescue (Festuca arundinacea Schreb.)1

“…I N recent years there have been several reports 3 (3,5,7,8,9) of the occurrence of alkaloids in tall fescue. Because alkaloids are known to have various physiological effects on mammals, and because tall fescue is a well adapted, widely used pasture grass in the southeastern United States it is important to know more about the alkaloids of this species.…”

Advanced Data-Mining Strategies for the Analysis of Direct-Infusion Ion Trap Mass Spectrometry Data from the Association of Perennial Ryegrass with Its Endophytic Fungus,Neotyphodium lolii

“…Perloline (m/z 333), a diazaphenanthrene alkaloid, is produced by the grass plant and has been isolated from both ryegrass and tall fescue plants (Grimmett and Waters, 1943;Jeffreys, 1964;Bush and Jeffreys, 1975). Our results suggest that perloline concentrations are reduced in endophyte-infected mature blades and sheaths; the mechanism for this effect remains to be elucidated.…”