1962/03/01 by WD Crow
Agricultural and Biological Sciences · #Botanical Research and Chemistry #Plant and fungal interactions
paper · doi:10.1071/ch9620159
The immense economic importance of the grasses has led to a large number of investigations, but these are primarily concerned with the use of such plants as pasture materials.The possibility that alkaloids might be present in grasses has nevertheless not been entirely overlooked.The occurrence of the indole bases, gramine in barley (von Euler and Hellstrom 1932) and 5-methoxy-Nmethyltryptamine in Phalaris aruwdinacea L. (Wilkinson 1958), are recorded in the literature, as also is the occurrence of perloline, C,,H,,O,N, (Melville and Grimmett 1941) in Lolium perenme.The same compound was later shown to occur in two other species of LoZium, as well as in Pestuca arundiwacea and Setaria lutescens by Reifer and White (1945), who examined a number of grasses specifically for alkaloids.More recently, Punusov and Akramov (1960) have isolated the pyrrolizidine derivatives loline, lolinine, and lolinidine from LoZium ouneaturn.The observation that Thelepogon elegans, a sample of which was available from the Plant Introduction Section, C.S.I.R.O., contained alkaloids, was therefore followed up by extraction and isolation of the constituents.Paper chromatography showed the presence of at least five bases, two of which were isolated in sufficient amount for purification.Thelepogine (C,,H,,ON) showed the presence of an hydroxyl group (3300 em-l) in the infrared, but was transparent a t ~/20000 in the ultraviolet.The associated base thelepogidine (C,,H,,O,N) showed no evidence of hydroxyl or carbonyl absorption in the infrared, so that both oxygen atoms must be in the form of ether linkages.I n view of the shortage of material a heavy atom derivative of thelepogine was prepared for X-ray dBraction studies.The methiodide was examined by Fridrichsons and Mathieson (1960) of these Laboratories who have reported the structure (I) as a result of their investigations, and have indicated a possible