Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.
The polyhydroxy alkaloid glycosidase inhibitors swainsonine [1] and calystegine B2 [6] have been identified as constituents of the seeds of the Australian plant Ipomoea sp. Q6 [aff. calobra] (Weir vine) by gas chromatography-mass spectrometry and by their biological activity as inhibitors of specific glycosidases. This plant, which is known only from a small area of southern Queensland, has been reported to produce a neurological disorder when consumed by livestock. The extract of the seeds showed inhibition of alpha-mannosidase, beta-glucosidase, and alpha-galactosidase, consistent with the presence of 1 and alkaloids of the calystegine class. Histological examination of brain tissue from field cases of sheep and cattle poisoned by Weir vine showed lesions similar to those observed in animals poisoned by the swainsonine-containing poison peas (Swainsona spp.) of Australia and locoweeds (Astragalus and Oxytropis spp.) of North America. These results indicate that Weir vine poisoning is an additional manifestation of the induced lysosomal storage disease, mannosidosis, possibly exacerbated by inhibition of the enzymes beta-glucosidase and alpha-galactosidase by calystegine B2. This is the first reported example of a single plant species capable of producing structurally distinct glycosidase inhibitors, namely, alkaloids of the indolizidine and nortropane classes.
Molyneux
R J
RJ
Western Regional Research Center, USDA, Albany, California 94710, USA.
McKenzie
R A
RA
O'Sullivan
B M
BM
Elbein
A D
AD
D001315:Australia; D001643:Bridged Bicyclo Compounds / Q000302:isolation & purification* / Q000494:pharmacology; D002852:Chromatography, Ion Exchange; D008401:Gas Chromatography-Mass Spectrometry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D009662:Nortropanes; D010947:Plants, Toxic / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D012991:Solanaceous Alkaloids; D017026:Swainsonine / Q000302:isolation & purification* / Q000494:pharmacology
D001643:Bridged Bicyclo Compounds; D009662:Nortropanes; D012991:Solanaceous Alkaloids; C095613:calystegine B(2); D006026:Glycoside Hydrolases; D017026:Swainsonine