title: Pipestelides A-C: cyclodepsipeptides from the Pacific marine sponge Pipestela candelabra.
abstract: Pipestelides A-C (2-4) are three new NRPS-PKS hybrid macrolides containing uncommon moieties, isolated from the Pacific marine sponge Pipestela candelabra. Their structures were elucidated on the basis of spectroscopic data. These cyclodepsipeptides appear to be biosynthetically related to jaspamide (aka jasplakinolide) (1) by chemical modification of the building blocks of the polyketide or peptide chains. Pipestelides A-C (2-4) contain a bromotyrosine [3-amino-3-(bromo-4-hydroxyphenyl)propanoic acid] unit, a polypropionate with a Z double bond, and a 2-hydroxyquinolinone, respectively. Revised chemical shift assignments are provided for the co-isolated known jasplakinolide C(a) (5). In addition, compounds 2 and 3 exhibited cytotoxic activities in the micromolar range.
authors.affiliation: Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, ICSN-CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sorres
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Sylvain
authors.initials: S
authors.lastname: Petek
authors.forename: Hélène
authors.initials: H
authors.lastname: Levaique
authors.forename: Thierry
authors.initials: T
authors.lastname: Cresteil
authors.forename: Suzanne
authors.initials: S
authors.lastname: Ramos
authors.forename: Odile
authors.initials: O
authors.lastname: Thoison
authors.forename: Cécile
authors.initials: C
authors.lastname: Debitus
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
mesh_terms: D000818:Animals; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D008386:Marine Biology; D008542:Melanesia; D019906:Nuclear Magnetic Resonance, Biomolecular; D010140:Pacific Ocean; D011161:Porifera / Q000737:chemistry*
chemical_list: D047630:Depsipeptides; C573606:pipestelide A; C573608:pipestelide B; C573607:pipestelide C; C057531:jasplakinolide