Showing papers in "Journal of Organic Chemistry in 1959"

Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis

Abstract: Several plants which we have studied recently have, by coincidence, yielded indole alkaloids of simple structure. Four of these are described in the present paper. Although numerous members of the maple family, Aceraceae, have been studied chemically in considerable detail, none has been known to produce alkaloids. When we learned, through qualitative tests, that alkaloids occur in the leaves of the silver maple tree, Acer saccharinum L. it was of considerable interest to us to learn their nature. Extraction of 3.75 kg. of dried, ground maple leaves2 with ethanol and concentration of the alkaloid gave a mass of large crystals in 0.05% yield. The ultraviolet spectrum of the material was almost identical with those of 3-substituted indoles such :ts gramine and tryptamine. Upon recrystallization from benzene, the alkaloid melted a t 131-132\" and was found to be identical with a synthetic specimen of the alkaloid gramine (I). As far as we know, gramine has been found to occur naturally only in the grass family and its occurrence in maple leaves was quite unexpected. The Aceraceae may now be included in the growing number of plant families known to produce indole alkaloids.