Gramine (Gra)

Gramine is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms. Gramine has been found in the giant reed, Arundo donax, Acer saccharinum (Silver Maple), Hordeum, (a grass genus that includes barley) and Phalaris (another grass genus). Gramine is used mostly in synthetic organic chemistry as a starting material for tryptophan syntheses. All reactions of gramine follow the same general reaction scheme. Gramine is reacted with a strong electrophile, such as methyl iodide, to form the quaternary ammonium salt. The ammonium salt will undergo a Hofmann elimination or Michael addition to give the very active intermediate, which can accept a wide range of nucleophiles to give the desired product. Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).