Idiospermine and other biogenetically related alkaloids

Alkaloids biogenetically related to idiospermine have been isolated from sources other than plants. For example, (-)-calycanthine and (+)-chimonanthine have been isolated from the Columbian poisondart frog, Phyllobates terribilis. The communesins have been isolated from a strain of Penicillum sp. marine fungus while perophoramidine has been isolated from the fungus Perophora namei (Ascidiaceae).

A list of the alkaloids biogenetically related to idiospermine include:

• Calycanthine
• Chimonanthine
• Calycanthidine (a mono methylated derivative of chimonanthine)
• Folicanthine (a di methylated derivative of chimonanthine)
• Chimonanthidine (same as calycanthidine but with the third methyl on an indole N rather than an indolamine N)
• Hodgkisine (related to chimonanthine – consisting of three N-methyl tryptamine units)
• Qudrigemine (related to chimonanthine – consisting of four N- methyl tryptamine units)
• Idiosperumline (a mono methylated derivative of hodgkinsine)
• Psychotrimine (related to chimonanthine – consisting of three N-methyl tryptamine units with an indole N bonded to a C7 position of chimonanthine)
• Psychopentamine (related to chimonanthine – consisting of five N-methyl tryptamine units with an indole N bonded to a C7 position of chimonanthine)
• Idiospermamine (consisting of three N-methyl tryptamine units with a calycanthine moiety attached to a beta position of an N-methyl tryptamine unit followed by cyclisation to form a pyrrolidine ring)
• Calycosidine (consisting of a calycanthine moiety attached to a pyrrolidinoindole moiety)
• Psycholeine (consisting of a calycanthine moiety attached to a pyrrolidinoindole moiety at each of the C8 positions)
• Psychotridine (consisting of five N-methyl tryptamine units)
• Isopsychotridine (consisting of five N-methyl tryptamine units)
• Vatine and Vatine-A (both consisting of six N-methyl tryptamine units)
• Vatamine (consisting of seven N-methyl tryptamine units)
• Vatamidine (consisting of eight N-methyl tryptamine units)
• Perophoramidine
• CPC-2

A helpful overview of the biogenesis of these alkaloids may be found in Jeremy A. May and Brian Stoltz, “The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins and nomofungin”, Tetrahedron, vol. 62 (2006), pp5262-5271.