title: Biosynthesis and cellular localization of functional polyketides in the gastropod mollusc Scaphander lignarius.
abstract: Opisthobranchs belong to a subclass of highly evolved and specialised marine gastropods that rely on the use of secondary metabolites for their survival. Here we report the full elucidation of the biosynthesis of aromatic metabolites, lignarenones, in one of these gastropods, the cephalaspidean Scaphander lignarius. Feeding experiments with ²H- and ¹³C-labelled precursors revealed a mixed acetate/propionate polyketide pathway primed by benzoic acid. Phenylalanine ammonia lyase (PAL), unprecedented in animals, is central to the synthesis of this aromatic precursor by oxidative deamination of L-phenylalanine to cinnamic acid. Lignarenones are synthesised in the cytoplasm of specialised eukaryotic cells named Blochmann's glands, which are distributed in biosynthetic tissue localised in the vulnerable mantle of the mollusc. This result supports the hypothesis that this lineage of gastropods has acquired the genetic information to produce the chemical substances that they use for their survival.
authors: Consiglio Nazionale delle Ricerch, Istituto di Chimica Biomolecolare, Via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy.
authors: Adele
authors: A
authors: Cutignano
authors: Conxita
authors: C
authors: Avila
authors: Annamaria
authors: A
authors: Rosica
authors: Giovanna
authors: G
authors: Romano
authors: Bruna
authors: B
authors: Laratta
authors: Anna
authors: A
authors: Domenech-Coll
authors: Guido
authors: G
authors: Cimino
authors: Ernesto
authors: E
authors: Mollo
authors: Angelo
authors: A
authors: Fontana
mesh_terms: D000818:Animals; D059001:Aquatic Organisms; D019817:Benzoic Acid / Q000378:metabolism; D002247:Carbon Isotopes; D002934:Cinnamates / Q000378:metabolism; D003593:Cytoplasm / Q000378:metabolism*; D003903:Deuterium; D005057:Eukaryotic Cells / Q000378:metabolism*; D049851:Gastropoda / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010649:Phenylalanine / Q000378:metabolism; D010650:Phenylalanine Ammonia-Lyase / Q000378:metabolism*; D011090:Polyenes / Q000378:metabolism; D061065:Polyketides / Q000378:metabolism*; D011422:Propionates / Q000378:metabolism
chemical_list: D002247:Carbon Isotopes; D002934:Cinnamates; D011090:Polyenes; D061065:Polyketides; D011422:Propionates; C029010:cinnamic acid; D010649:Phenylalanine; D019817:Benzoic Acid; D003903:Deuterium; D010650:Phenylalanine Ammonia-Lyase