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Discovery of a Short‐Chain Dehydrogenase from Catharanthus roseus that Produces a New Monoterpene Indole Alkaloid
Author(s) -
Stavrinides Anna K.,
Tatsis Evangelos C.,
Dang ThuThuy,
Caputi Lorenzo,
Stevenson Clare E. M.,
Lawson David M.,
Schneider Bernd,
O'Connor Sarah E.
Publication year - 2018
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.201700621
Subject(s) - aglycone , catharanthus roseus , monoterpene , indole alkaloid , indole test , chemistry , natural product , stereochemistry , apocynaceae , biology , biochemistry , botany , glycoside
Abstract 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.