Isolation and NMR Study on Swainsonine from Locoweed, Astragalus strictus

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Abstract

Locoweed is a poisonous plant wildly distributed in most area of the world and can cause livestock poisoning or death with significant economic loss. The principal responsible for its toxicity is indolizidine alkaloid swainsonine, a new potential anticancer and antiviral drug. Astragalus strictus is mainly distributed in Tibet of China and is a serious hazard to the local livestock industry. To analyze its main toxic ingredients and supply more structural information and more accurate data, swainsonine has been isolated from this plant by D101 macroporous resin and the 1H and 13C chemical shifts of the compound has been assigned by 1D-NMR and 2D-NMR techniques. At the same time, complete assignments of swainsonine's 13C spectral signals are reported.

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    Swainsonine (378) could be obtained in gram quantities from extracts of A. lentiginosus by subjecting the basic aqueous fraction eluted from an ion-exchange column to continuous liquid–liquid extraction with dichloromethane, then purifying the alkaloid either by recrystallization from ammonia-saturated chloroform, by sublimation, or via a chloroform-soluble methylboronate derivative.208 Purification of swainsonine from the Tibetan species A. strictus by passage through D101 macroporous resin gave a sample of sufficient quality for thorough NMR spectroscopic analysis that included a full assignment of 13C signals,209 while ultrasound-assisted solvent extraction has been found to promote isolation and purification of the alkaloid from the Chinese locoweed O. ochrocephala.210 Detection of swainsonine in biological samples is also of interest; for example, a simple HPLC-UV method was reported for detecting the alkaloid in rat plasma.211

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    The evolutionary importance of locoweed SWA remains unclear, as it may not function as an anti-herbivore compound. Vertebrate livestock and wildlife consume locoweeds and subsequently suffer chronic damage and even death in the USA (Molyneux and Ralphs, 1992) as well as China, Tibet, and Mongolia (Zhao et al., 2009). Consistent with this observation is that high SWA var.

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    Locoweed poisoning is the most widespread poisonous plant problem in China and the western United States, and causes great economic losses to the livestock industry (James and Panter, 1989; Li and Wang, 2003). The indolizidine alkaloid swainsonine (Fig. 1), which was first isolated from Swainnona canescens (Colegate et al., 1979) and subsequently from spotted locoweed, is the toxin responsible for inducing locoweed poisoning in animals (Molyneux and James, 1982; Ralphs et al., 2002; Zhao et al., 2009). In the past few years, a swainsonine-producing fungal endophyte, Undifilum oxytropis, previously annotated as Embellesia oxytropis, has been isolated from locoweeds (Braun et al., 2003; Yu et al., 2010).

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