title: Bioactive dehydrotyrosyl and dehydrodopyl compounds of marine origin.
abstract: The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa-containing compounds possess dehydro groups in their side chains. Examples span the range from simple dehydrotyrosine and dehydrodopamines to complex metabolic products, including peptides and polycyclic alkaloids. Based on structural information, these compounds can be subdivided into five categories: (a) Simple dehydrotyrosine and dehydrotyramine containing molecules; (b) simple dehydrodopa derivatives; (c) peptidyl dehydrotyrosine and dehydrodopa derivatives; (d) multiple dehydrodopa containing compounds; and (e) polycyclic condensed dehydrodopa derivatives. These molecules possess a wide range of biological activities that include (but are not limited to) antitumor activity, antibiotic activity, cytotoxicity, antioxidant activity, multidrug resistance reversal, cell division inhibition, immunomodulatory activity, HIV-integrase inhibition, anti-viral, and anti-feeding (or feeding deterrent) activity. This review summarizes the structure, distribution, possible biosynthetic origin, and biological activity, of the five categories of dehydrotyrosine and dehydrodopa containing compounds.
authors.affiliation: Department of Biology, University of Massachusetts Boston, MA 02125, USA. manickam.sugumaran@umb.edu
authors.forename: Manickam
authors.initials: M
authors.lastname: Sugumaran
authors.forename: William E
authors.initials: WE
authors.lastname: Robinson
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D059001:Aquatic Organisms / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D007448:Invertebrates / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry / Q000627:therapeutic use; D011083:Polycyclic Compounds / Q000737:chemistry / Q000627:therapeutic use; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001688:Biological Products; D010455:Peptides; D011083:Polycyclic Compounds; D014443:Tyrosine; D004295:Dihydroxyphenylalanine