title: Parallel synthesis and anti-inflammatory activity of cyclic peptides cyclosquamosin D and Met-cherimolacyclopeptide B and their analogs.
abstract: We report the parallel synthesis of two natural cyclopeptides, isolated from the seeds of Annona squamosa, cyclosquamosin D (A1), and Met-cherimolacyclopeptide B (B) and their analogs. All of the compounds were screened for anti-inflammatory activity by evaluating their inhibitory effects on the production of pro-inflammatory cytokines using the lipopolysaccharide stimulated macrophage J774A.1 cell line. Compounds having significant anti-inflammatory activity in suppressing the secretion of IL-6 and TNF-α have been identified, some of which exhibit activity superior to that observed with the natural products.
authors.affiliation: Faculté de Pharmacie, Laboratoire de Pharmacologie Marine, 5000 Monastir, Tunisia.
authors.forename: Afef
authors.initials: A
authors.lastname: Dellai
authors.forename: Igor
authors.initials: I
authors.lastname: Maricic
authors.forename: Vipin
authors.initials: V
authors.lastname: Kumar
authors.forename: Sergey
authors.initials: S
authors.lastname: Arutyunyan
authors.forename: Abderrahman
authors.initials: A
authors.lastname: Bouraoui
authors.forename: Adel
authors.initials: A
authors.lastname: Nefzi
mesh_terms: D000818:Animals; D031041:Annona / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D015850:Interleukin-6 / Q000378:metabolism; D051379:Mice; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D015850:Interleukin-6; C555988:Met-cherimolacyclopeptide B; D010456:Peptides, Cyclic; D014409:Tumor Necrosis Factor-alpha; C527767:cyclosquamosin D
references.citation: J Nat Prod. 2005 Nov;68(11):1686-8
references.pmid: 16309326
references.citation: Arch Pharm Res. 2007 Nov;30(11):1380-6
references.pmid: 18087804
references.citation: J Immunol. 2009 Jun 1;182(11):6959-68
references.pmid: 19454693
references.citation: Science. 1986 Apr 18;232(4748):341-7
references.pmid: 3961484
references.citation: Chemistry. 2008;14(12):3620-9
references.pmid: 18278777
references.citation: Biopolymers. 2008;90(3):175-84
references.pmid: 18213693
references.citation: Int J Pept Protein Res. 1990 Mar;35(3):161-214
references.pmid: 2191922
references.citation: J Immunol. 2006 Dec 1;177(11):7645-55
references.pmid: 17114434
references.citation: J Agric Food Chem. 2008 Jan 23;56(2):386-92
references.pmid: 18072745
references.citation: Science. 1993 Jul 16;261(5119):308-9
references.pmid: 8392747
references.citation: J Antibiot (Tokyo). 1982 Sep;35(9):1130-6
references.pmid: 7142019
references.citation: Org Biomol Chem. 2009 Jan 21;7(2):259-68
references.pmid: 19109670
references.citation: J Nat Prod. 2006 Oct;69(10):1435-41
references.pmid: 17067157
references.citation: Chem Rev. 2005 Dec;105(12):4441-82
references.pmid: 16351050