title: Biosynthesis of sesquiterpene lactones in pyrethrum (Tanacetum cinerariifolium).
abstract: The daisy-like flowers of pyrethrum (Tanacetum cinerariifolium) are used to extract pyrethrins, a botanical insecticide with a long history of safe and effective use. Pyrethrum flowers also contain other potential defense compounds, particularly sesquiterpene lactones (STLs), which represent problematic allergenic residues in the extracts that are removed by the pyrethrum industry. The STLs are stored in glandular trichomes present on the pyrethrum achenes, and have been shown to be active against herbivores, micro-organisms and in the below-ground competition with other plants. Despite these reported bioactivities and industrial significance, the biosynthetic origin of pyrethrum sesquiterpene lactones remains unknown. In the present study, we show that germacratrien-12-oic acid is most likely the central precursor for all sesquiterpene lactones present in pyrethrum. The formation of the lactone ring depends on the regio- (C6 or C8) and stereo-selective (α or β) hydroxylation of germacratrien-12-oic acid. Candidate genes implicated in three committed steps leading from farnesyl diphosphate to STL and other oxygenated derivatives of germacratrien-12-oic acid were retrieved from a pyrethrum trichome EST library, cloned, and characterized in yeast and in planta. The diversity and distribution of sesquiterpene lactones in different tissues and the correlation with the expression of these genes are shown and discussed.
authors.affiliation: Plant Research International, Wageningen University and Research Centre, Wageningen, The Netherlands.
authors.forename: Aldana M
authors.initials: AM
authors.lastname: Ramirez
authors.forename: Nils
authors.initials: N
authors.lastname: Saillard
authors.forename: Ting
authors.initials: T
authors.lastname: Yang
authors.forename: Maurice C R
authors.initials: MC
authors.lastname: Franssen
authors.forename: Harro J
authors.initials: HJ
authors.lastname: Bouwmeester
authors.forename: Maarten A
authors.initials: MA
authors.lastname: Jongsma
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000235:genetics / Q000378:metabolism; D001692:Biological Transport; D053898:Biosynthetic Pathways; D011723:Chrysanthemum cinerariifolium / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D018506:Gene Expression Regulation, Plant; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D010940:Plant Proteins / Q000235:genetics / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D064201:Trichomes / Q000737:chemistry / Q000648:ultrastructure; D015003:Yeasts / Q000235:genetics / Q000378:metabolism
chemical_list: D007783:Lactones; D010940:Plant Proteins; D012717:Sesquiterpenes; D019883:Alkyl and Aryl Transferases