Stemona alkaloids: biosynthesis, classification, and biogenetic relationships.

Stemona alkaloids form a unique class, which can be attributed to hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine-class alkaloids originated from L-ornithine and glutamic acid. By the end of 2013, approximately 183 Stemona alkaloids had been isolated from nature. The literature on Stemona alkaloids in the realms of chemical structure, synthesis, and bioactivities has been elegantly summarized and reviewed. We thus summarize in this review the biosynthesis, structural classification, and the intrinsic, biogenetic relationships of Stemona alkaloids. Based on the comprehensive consideration of biogenetic pathways and chemical features, the 183 Stemona alkaloids are classified into two classes (hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine) and fourteen types.