Role of hypaphorine in the toxicity ofAstragalus lusitanicus

Abstract

Hypaphorine, an alpha-N,N,N-trimethyltryptophan betaine, was isolated, for the first time, from Astragalus lusitanicus Lam. (Fabaceae), a plant highly toxic for lambs and goats. This alkaloid was characterized by NMR and MS analysis. Hypaphorine was previously reported to be a convulsive poison. To confirm the toxicity, it was synthesized and tested in goats. Hypaphorine was shown to be non-toxic for goats even at a high dose of 2 g kg(-1) by oral administration.

Major alkaloidal constituent from Impatiens niamniamensis seeds as antihyperglycemic agent

“…The quaternary carbon at d 171.2 was assigned to carboxylic group (C-12), exhibited cross peaks with H-10 and H-11. The structure of compound was thus characterized as known a-N,N, N-trimethyltryptophan betaine, trivially known as hypaphorine, which was further confirmed by matching its spectroscopic data with that reported in literature (Kassaoui et al, 2008).…”

“…Hypaphorine was previously reported to be a convulsive poison. However, later studies showed that it is not toxic (Kassaoui et al, 2008). It inhibits root hair tip growth (Dauphin et al, 2007).…”

Astraodoric Acids A–D: New Lanostane Triterpenes from Edible Mushroom Astraeus odoratus and Their Anti-Mycobacterium tuberculosis H37Ra and Cytotoxic Activity

“…Three methyl carbons attached to the nitrogen atom were observed as a singlet signal at δ C 52.8, and their methyl protons showed resonance signals at δ H 4.62 (N + Me 3 ). By comparing the 1 H and 13 C NMR spectra data with those reported from literature, 19 compound 8 was identified as a known hypaphorine.…”

“…26 In fungi, hypaphorine is an antagonist against an IAA (indole-3-acetic acid) that inhibits the root hair tip growth and hair elongation. 19 Recent studies 27 have shown that hypaphorine extracted from Impatiens niamniamensis seeds was an antihyperglycemic agent and showed some activities in streptozotocin-induced diabetic rats. This paper 27 also reviewed previous work where hypaphorine promoted sleep in mice and stimulated the fermentation process in normal male Long− Evans rats that lead to changes in phosphoenolpyruvate carboxykinase activity.…”

Phylogeny and genetic structure of Erophaca (Leguminosae), a East–West Mediterranean disjunct genus from the Tertiary

“…By mid spring (May) the plants shed their leaves, all above ground plant parts senesce and become dry, and the buried xylopodia become dormant until next winter. Throughout its distribution range populations occur as isolated patches, usually in cork oak (Quercus suber) woodlands from sea level up to 1300 m. The foliage is very toxic to sheep, goats and cattle (Bel-Kassaoui et al, 2008) and for this reason plants are sometimes cut down by shepherds and farmers, presumably to prevent them from spreading (Casimiro-Soriguer, personal observation). Consequently, in parts of its range (particularly Morocco) humans may have decimated populations for centuries.…”