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Biosynthesis and Cellular Localization of Functional Polyketides in the Gastropod Mollusc Scaphander lignarius
Author(s) -
Cutignano Adele,
Avila Conxita,
Rosica Annamaria,
Romano Giovanna,
Laratta Bruna,
DomenechColl Anna,
Cimino Guido,
Mollo Ernesto,
Fontana Angelo
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200287
Subject(s) - biosynthesis , biology , biochemistry , phenylalanine , polyketide , biogenesis , gene , amino acid
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 2 H‐ and 13 C‐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.