Eudistoma Shermilamines

Tunicates are the only marine invertebrates in which alkaloid biosynthesis has been extensively investigated (189). In addition to the eudistomins, described below, the tripeptide tunichromes have been investigated, by Nakanishi and coworkers at Columbia University, in the solitary tunicate Ascidia nigra (191) and shermilamine, a benzo-3,6-phenanthroline alkaloid, has been studied in Cystodytes dellechiajei, by Steffan and coworkers at the University of Munich (192). The origin of the (3-carboline ring system of the eudistomins has been studied, by Baker s group at Florida Tech, in Eudistoma olivaceum (193, 194). 

Shermilamines A and B were isolated from a purple Trididemnum sp. [146,147], while shermilamine C was reported from a purple fleshy Cystodytes sp. from Fiji [132]. Both shermilamines A and B were reported in a paper which described metabolites from Amphicarpa meridiana and Leptoclinides sp. [145], while shermilamine B was also reported under the name debromoshermilamine from a Red Sea Eudistoma sp, [135]. Biosynthetic studies on shermilamine B have been reported [150]. The... 

Eudistones A and B were obtained from an undetermined species of Eudistoma from the Seychelles Islands. Tintamine, shermilamine E and cydoshermil-amine D are three sulfur-containing pyridoacridines. These new alkaloids were extracted from Cystodytes viola-tinctus, whose specific name refers to the animal s color and whose origin is the lagoon of Mayotte. Tintamine is the first example of a pyridoacridine associated with a tropolone and shermilamine E is a rare example of an N-oxide derivative isolated from a marine organism. 

---