Isolation and characterization of 3‐methoxy‐2(5H)‐furanone as the principal nephrotoxin from Narthecium ossifragum (L.) Huds.

Abstract

The principal substance in Narthecium ossifragum (L.) Huds, responsible for the nephrotoxic effects on cattle, moose, goats and other ruminants has been isolated and identified by X-ray crystallography as 3-methoxy-2(5H)-furanone. The Fourier-transform infra-red, 1H and 13C nuclear magnetic resonance, and mass spectra are also given. The concentration in four different batches of plant material varied from 113 to 344 microg g(-1) (wet weight). Extracts of N. ossifragum and fractions derived from them, including purified 3-methoxy-2(5H)-furanone, were each dosed intraruminally, to young goats. 3-Methoxy-2(5H)-furanone of 99.9% purity (15 mg kg(-1) live weight) caused increased concentration of creatinine in serum within 2-3 days, typical of kidney damage caused by N. ossifragum, while toxic effect was obtained down to 4 mg kg(-1) live weight with less purified material (> or = 95%). Toxic effect was also obtained with synthesized 3-methoxy-2(5H)-furanone (30 mg kg(-1) live weight). The isomer 4-methoxy-2(5H)-furanone, detected in some of the batches of the plant material, was not toxic when dosed at 60 mg kg(-1) live weight.

Narthecium ossifragum(L.) Huds. Causes Kidney Damage in Goats: Morphologic and Functional Effects

“…19 In Japan, the plant Narthecium asiaticum causes intoxication in cattle, with clinical, biochemical, and pathologic changes similar to those described for N. ossifragum-intoxicated cattle. 28 3M2F is also isolated from this plant.…”

“…In experiment 2, the extract was produced in the same way as in experiment 1, and the concentration of 3M2F was measured to 454 g/ ml by the method of Langseth et al (1999). 19 …”

“…Thirteen Norwegian dairy goats (Nos. [13][14][15][16][17][18][19][20][21][22][23][24][25] from the same herd, 11 males and two females, 5-7 week old, 6-to 11-kg body weight (mean 8.5 kg), were included. Four goats were kept as controls throughout the experiment (Nos.…”

Suspected bog asphodel (Narthecium ossifragum) toxicity in cattle in North Wales

“…The active toxic component has been identified as 3-methoxy-2(5H)-furanone (Langseth and others 1999). The clinical signs associated with bog asphodel toxicity include depression, anorexia, malaena or fresh blood in faeces, diarrhoea and death in many cases.…”

Liliaceae Juss.

“…They are cultivated in all parts of our range as garden plants or houseplants. The toxin in Narthecium that causes kidney disease appears to be 3 -methoxy-2furanone, although tannin concentrations are also high (10%) (Suzuki et al 1985;Fla øyen 1998;Langseth et al 1999). Like so many other genera of the family, the genus contains several steroidal saponins of unknown toxicologic signifi cance (Shimomura et al 1989).…”