Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids.
[reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).
Vergne
Carine
C
Institut de Chimie des Substances Naturelles du CNRS, Gif-sur-Yvette, France.
Boury-Esnault
Nicole
N
Perez
Thierry
T
Martin
Marie-Thérèse
MT
Adeline
Marie-Thérèse
MT
Tran Huu Dau
Elise
E
Al-Mourabit
Ali
A
D000470:Alkaloids / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D047089:Axinella / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry* / Q000302:isolation & purification
D000470:Alkaloids; D010456:Peptides, Cyclic; D010879:Piperazines; C518054:cyclo(prolylarginyl); C518053:cyclo(prolylprolyl); C465248:phakellin