title: Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities.
abstract: All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8'R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity.
authors: Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors: Hisashi
authors: H
authors: Nishiwaki
authors: Mitsuko
authors: M
authors: Kumamoto
authors: Yoshihiro
authors: Y
authors: Shuto
authors: Satoshi
authors: S
authors: Yamauchi
mesh_terms: D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018525:Germination / Q000187:drug effects; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008129:Lolium / Q000187:drug effects / Q000254:growth & development; D063245:Plant Development; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D010944:Plants / Q000187:drug effects*; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D005663:Furans; D017705:Lignans; C060282:lariciresinol