Journal
CHEMBIOCHEM
Volume 13, Issue 12, Pages 1759-1766Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201200287
Keywords
bacteria; chemical defense; invertebrates; natural products; polyketides; symbiosis
Funding
- Italian Research Council (CNR)
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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.
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