title: Two cytochromes P450 catalyze S-heterocyclizations in cabbage phytoalexin biosynthesis.
abstract: Phytoalexins are abundant in edible crucifers and have important biological activities, yet no dedicated gene for their biosynthesis is known. Here, we report two new cytochromes P450 from Brassica rapa (Chinese cabbage) that catalyze unprecedented S-heterocyclizations in cyclobrassinin and spirobrassinin biosynthesis. Our results provide genetic and biochemical insights into the biosynthesis of a prominent pair of dietary metabolites and have implications for pathway discovery across >20 recently sequenced crucifers.
authors.affiliation: Department of Chemical Engineering, Stanford University, Stanford, California, USA.
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Klein
authors.affiliation: Department of Chemical Engineering, Stanford University, Stanford, California, USA.
authors.forename: Elizabeth S
authors.initials: ES
authors.lastname: Sattely
mesh_terms: D001483:Base Sequence; D055162:Biocatalysis; D029741:Brassica rapa / Q000201:enzymology* / Q000235:genetics; D019607:Brassicaceae / Q000201:enzymology* / Q000235:genetics; D003500:Cyclization; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D015870:Gene Expression; D059014:High-Throughput Nucleotide Sequencing; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D007527:Isoenzymes / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D007700:Kinetics; D008861:Microsomes / Q000737:chemistry / Q000378:metabolism; D008969:Molecular Sequence Data; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D010940:Plant Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D012333:RNA, Messenger / Q000235:genetics / Q000378:metabolism; D011994:Recombinant Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D013141:Spiro Compounds / Q000737:chemistry / Q000378:metabolism*; D013844:Thiazoles / Q000737:chemistry / Q000378:metabolism*; D013859:Thiocarbamates / Q000737:chemistry / Q000378:metabolism*; D014675:Vegetables / Q000737:chemistry / Q000378:metabolism; D000094162:Phytoalexins
chemical_list: D007211:Indoles; D007527:Isoenzymes; D010940:Plant Proteins; D012333:RNA, Messenger; D011994:Recombinant Proteins; D012717:Sesquiterpenes; D013141:Spiro Compounds; D013844:Thiazoles; D013859:Thiocarbamates; C581768:cyclobrassinin; C417935:spirobrassinin; D003577:Cytochrome P-450 Enzyme System; D000094162:Phytoalexins