title: 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.
authors.affiliation: National Veterinary Institute, Department of Chemistry, Oslo, Norway. wenche.langseth@vetinst.no
authors.forename: W
authors.initials: W
authors.lastname: Langseth
authors.forename: T
authors.initials: T
authors.lastname: Torgersen
authors.forename: P
authors.initials: P
authors.lastname: Kolsaker
authors.forename: C
authors.initials: C
authors.lastname: Rømming
authors.forename: T G
authors.initials: TG
authors.lastname: Jantsch
authors.forename: P G
authors.initials: PG
authors.lastname: Mantle
authors.forename: J
authors.initials: J
authors.lastname: Pearce
authors.forename: S E
authors.initials: SE
authors.lastname: Gibson
authors.forename: M G
authors.initials: MG
authors.lastname: Goicochea
authors.forename: A
authors.initials: A
authors.lastname: Flåøyen
mesh_terms: D000818:Animals; D002417:Cattle; D018360:Crystallography, X-Ray; D005663:Furans / Q000302:isolation & purification* / Q000633:toxicity; D007668:Kidney / Q000187:drug effects*; D013058:Mass Spectrometry; D010947:Plants, Toxic / Q000737:chemistry*
chemical_list: C403722:3-methoxy-2(5H)-furanone; D005663:Furans