Alkaloids constitute the largest class of plant secondary compounds, occurring in 20 to 30% of perennial herbaceous species in North America. Alkaloid-containing plants are of interest, first because alkaloids often have pronounced physiological reactions when ingested by livestock, and second because alkaloids have distinctive taste characteristics. Thus, alkaloids may kill, injure, or reduce ...

Swainsonine, an indolizidine alkaloid, has been found to inhibit the experimental metastasis of B16-F10 melanoma cells when administered systemically to syngeneic C57BL/6 mice. The inhibition was both potent and dose dependent with greater than or equal to 80% reduction in pulmonary colonization being observed after only 24-h exposure to 3 micrograms/ml of swainsonine in drinking water. In cont...

With few exceptions, aposematically colored poison frogs sequester defensive alkaloids, unchanged, from dietary arthropods. In the Neotropics, myrmicine and formicine ants and the siphonotid millipede Rhinotus purpureus are dietary sources for alkaloids in dendrobatid poison frogs, yet the arthropod sources for Mantella poison frogs in Madagascar remained unknown. We report GC-MS analyses of ex...

The first detailed studies of intramolecular aza-Prins and aza-silyl-Prins reactions, starting from acyclic materials, are reported. The methods allow rapid and flexible access toward an array of [6,5] and [6,6] aza-bicycles, which form the core skeletons of various alkaloids. On the basis of our findings on the aza-Prins and aza-silyl-Prins cyclizations, herein we present simple protocols for ...

A new and efficient enantioselective total synthesis of the title deoxycastanospermine derivative has been developed, based on amino acid and b-ketophosphonate chemistry, as well as employment of internal asymmetric induction for the creation of the new chiral centers proved successful. With proper choice of reaction conditions, the approach can also be applied in selective preparation of sever...