Discovery of a Short-Chain Dehydrogenase from Catharanthus roseus that Produces a New Monoterpene Indole Alkaloid.

Autor: Stavrinides AK; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK.; UMR DIADE, Institut de Recherche pour le Développement, BP 64501, 34394, Montpellier, France., Tatsis EC; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK., Dang TT; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK., Caputi L; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK., Stevenson CEM; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK., Lawson DM; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK., Schneider B; Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, 07745, Jena, Germany., O'Connor SE; Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK.
Jazyk: angličtina
Zdroj: Chembiochem : a European journal of chemical biology [Chembiochem] 2018 May 04; Vol. 19 (9), pp. 940-948. Date of Electronic Publication: 2018 Mar 22.
DOI: 10.1002/cbic.201700621
Abstrakt: Plant monoterpene indole alkaloids, a large class of natural products, derive from the biosynthetic intermediate strictosidine aglycone. Strictosidine aglycone, which can exist as a variety of isomers, can be reduced to form numerous different structures. We have discovered a short-chain alcohol dehydrogenase (SDR) from plant producers of monoterpene indole alkaloids (Catharanthus roseus and Rauvolfia serpentina) that reduce strictosidine aglycone and produce an alkaloid that does not correspond to any previously reported compound. Here we report the structural characterization of this product, which we have named vitrosamine, as well as the crystal structure of the SDR. This discovery highlights the structural versatility of the strictosidine aglycone biosynthetic intermediate and expands the range of enzymatic reactions that SDRs can catalyse. This discovery further highlights how a sequence-based gene mining discovery approach in plants can reveal cryptic chemistry that would not be uncovered by classical natural product chemistry approaches.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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