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Identification of the glycosidase inhibitors swainsonine and calystegine B2in weir vine (ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity

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Molyneux, R. J., McKenzie, R. A., O'Sullivan, B. M. and Elbein, A. D. (1995) Identification of the glycosidase inhibitors swainsonine and calystegine B2in weir vine (ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity. Journal of Natural Products, 58 . pp. 878-886. ISSN 0163-3864

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Article Link: https://doi.org/10.1021/np50120a009

Abstract

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 α-mannosidase, β-glucosidase, and α-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 β-glucosidase and α-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.

Item Type:Article
Subjects:Technology > Technology (General) > Chromatography
Science > Biology > Biochemistry
Live Archive:15 Feb 2024 23:07
Last Modified:15 Feb 2024 23:07

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