title: Synthesis of all stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol and their plant growth inhibitory activity.
abstract: All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.
authors.affiliation: Faculty of Agriculture, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.forename: Kumiko
authors.initials: K
authors.lastname: Nakayama
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shuto
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
mesh_terms: 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; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D017705:Lignans; D010937:Plant Growth Regulators
keywords: 3,3′-dimethoxy-7,7′-epoxylignane-4,4′-diol; Italian ryegrass; lettuce; lignan; plant growth inhibitory activity