title: Chemical and pharmacological significance of natural guanidines from marine invertebrates.
abstract: Natural Guanidines from marine invertebrates represent a group of bioactive secondary metabolites that revealed prominent pharmacological activities such as antimicrobial, antiproliferative, analgesic, and anti-coagulant properties. Acyclovir (Zovirax(®)), the first guanidine-derived pharmaceutical for the treatment of herpes infections since late 1970s, was synthesized based on a marine arabinosyl nucleoside, spongosine. Recently, ziconotide (Prialt(®)), a synthetic form of the marine-derived peptide (ω-conotoxin MVIIA) comprising a guanidine moiety, has been approved for the treatment of chronic pain. This review surveys over 130 compounds of guanidine-containing secondary metabolites from marine invertebrates with emphasis on their pharmacological significance and structure-activity relationships.
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitaetsstrasse 1, D-40225 Duesseldorf, Germany.
authors.forename: S S
authors.initials: SS
authors.lastname: Ebada
authors.forename: P
authors.initials: P
authors.lastname: Proksch
mesh_terms: D000818:Animals; D059001:Aquatic Organisms / Q000737:chemistry / Q000378:metabolism; D006146:Guanidines / Q000737:chemistry* / Q000494:pharmacology; D007448:Invertebrates / Q000737:chemistry* / Q000378:metabolism; D010455:Peptides / Q000737:chemistry / Q000494:pharmacology; D011743:Pyrimidines / Q000737:chemistry / Q000494:pharmacology; D011758:Pyrroles / Q000737:chemistry / Q000494:pharmacology; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D014443:Tyrosine / Q000031:analogs & derivatives / Q000494:pharmacology
chemical_list: D006146:Guanidines; D010455:Peptides; D011743:Pyrimidines; D011758:Pyrroles; D014443:Tyrosine; C015685:aplysinopsin; D014364:Tryptophan