Pipestelides A-C: cyclodepsipeptides from the Pacific marine sponge Pipestela candelabra

  • J Nat Prod. 2012 Apr 27;75(4):759-63. doi: 10.1021/np200714m.
Jonathan Sorres  1 ,  Marie-Thérèse Martin ,  Sylvain Petek ,  Hélène Levaique ,  Thierry Cresteil ,  Suzanne Ramos ,  Odile Thoison ,  Cécile Debitus ,  Ali Al-Mourabit
Affiliations
  • 1. 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.
PMID: 22364566 DOI: 10.1021/np200714m
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.