title: Biosynthesis of yatein in Anthriscus sylvestris.
abstract: Little is known about the biosynthesis of yatein, in spite of its importance as a typical heartwood lignan and a key biosynthetic intermediate of the antitumor lignan podophyllotoxin. The present study, based on individual administration of [13C]phenylalanine and deuterium labelled lignans and simultaneous administration of two distinct lignans labelled with deuterium atoms to Anthriscus sylvestris, established the two independent branch pathways from matairesinol, one to afford yatein via thujaplicatin, 5-methylthujaplicatin, and 4,5-dimethylthujaplicatin and the other to bursehernin via pluviatolide. The latter pathway did not lead to yatein, eliminating the presence of a metabolic grid from matairesinol to yatein.
authors.affiliation: Wood Research Institute, Kyoto University, Uji, Kyoto 611-0011, Japan.
authors.forename: Norikazu
authors.initials: N
authors.lastname: Sakakibara
authors.forename: Shiro
authors.initials: S
authors.lastname: Suzuki
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Umezawa
authors.forename: Mikio
authors.initials: M
authors.lastname: Shimada
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000096:biosynthesis* / Q000378:metabolism; D019661:Apiaceae / Q000378:metabolism*; D001593:Benzyl Compounds; D002247:Carbon Isotopes; D003903:Deuterium; D004149:Dioxoles; D005663:Furans / Q000378:metabolism; D007783:Lactones; D017705:Lignans / Q000737:chemistry / Q000378:metabolism; D013058:Mass Spectrometry / Q000379:methods; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000378:metabolism; D011033:Podophyllin / Q000031:analogs & derivatives* / Q000378:metabolism
chemical_list: D001593:Benzyl Compounds; D002247:Carbon Isotopes; D004149:Dioxoles; D005663:Furans; D007783:Lactones; D017705:Lignans; C452802:yatein; C023816:bursehernin; D010649:Phenylalanine; C068935:matairesinol; D011033:Podophyllin; D003903:Deuterium; D015107:4-Butyrolactone