title: Cystophloroketals A-E, Unusual Phloroglucinol-Meroterpenoid Hybrids from the Brown Alga Cystoseira tamariscifolia.
abstract: Cystophloroketals A-E (1-5), five new phloroglucinol-meroditerpenoid hybrids, have been isolated together with their putative biosynthetic precursor, the monocyclic meroditerpenoid 6, from the Mediterranean brown alga Cystoseira tamariscifolia. They represent the first examples of meroditerpenoids linked to a phloroglucinol through a 2,7-dioxabicyclo[3.2.1]octane moiety. The chemical structures, including absolute configurations, were elucidated on the basis of extensive spectroscopic analysis (HR-ESIMS, 1D and 2D NMR, and ECD) and TDDFT ECD calculations. Compounds 1-6 were tested for their antifouling activity against several marine colonizing species (bacteria, fungi, invertebrates, micro- and macroalgae). Compound 6 showed high potency for the inhibition of macrofoulers (invertebrates and macroalgae), while cystophloroketals B (2) and D (4) displayed strong inhibition of the germination of the two macroalgae tested and moderate antimicrobial activities (bacteria, microalgae, and fungi).
authors.affiliation: †Laboratoire de Chimie des Substances Naturelles et de Biomolécules, Université de Blida 1, Blida, Algérie.
authors.forename: Mohamed
authors.initials: M
authors.lastname: El Hattab
authors.affiliation: ‡Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences, Université Nice Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France.|§Laboratoire de Pharmacognosie et de Chimie des Substances Naturelles, UMR 8638 CNRS, Sorbonne Paris Cité, Faculté des Sciences Pharmaceutiques et Biologiques, Université Paris Descartes, 75006 Paris, France.
authors.forename: Grégory
authors.initials: G
authors.lastname: Genta-Jouve
authors.affiliation: †Laboratoire de Chimie des Substances Naturelles et de Biomolécules, Université de Blida 1, Blida, Algérie.
authors.forename: Naïma
authors.initials: N
authors.lastname: Bouzidi
authors.affiliation: ⊥MAPIEM, EA 4323, Université de Toulon, 83957 La Garde, France.
authors.forename: Annick
authors.initials: A
authors.lastname: Ortalo-Magné
authors.affiliation: ∥Biodimar/LEMAR, UMR 6539, IUEM, Université de Bretagne Occidentale, 29238 Brest, France.
authors.forename: Claire
authors.initials: C
authors.lastname: Hellio
authors.affiliation: ∇Observatoire du Milieu Marin Martiniquais, Fond Lahaye, 97233 Schoelcher, Martinique, FWI, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Maréchal
authors.affiliation: ⊥MAPIEM, EA 4323, Université de Toulon, 83957 La Garde, France.
authors.forename: Louis
authors.initials: L
authors.lastname: Piovetti
authors.affiliation: ‡Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences, Université Nice Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Olivier P
authors.initials: OP
authors.lastname: Thomas
authors.affiliation: ‡Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences, Université Nice Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France.|⊥MAPIEM, EA 4323, Université de Toulon, 83957 La Garde, France.
authors.forename: Gérald
authors.initials: G
authors.lastname: Culioli
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D057219:Biofouling / Q000517:prevention & control*; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000459:Phaeophyceae / Q000737:chemistry*; D010696:Phloroglucinol / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D012624:Seaweed / Q000187:drug effects; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D013729:Terpenes; D010696:Phloroglucinol