Synthesis and bioactivity of potassium beta-D-glucopyranosyl 12-hydroxy jasmonate and related compounds.
Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. beta-D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (-)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.
Nakamura
Yoko
Y
Department of Chemistry, Faculty of Science, Tohoku University, Sendai, Japan.
Miyatake
Ryoji
R
Inomata
Sho
S
Ueda
Minoru
M
D031289:Albizzia / Q000378:metabolism; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D054883:Oxylipins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
D003517:Cyclopentanes; D005960:Glucosides; D054883:Oxylipins; C534725:glucopyranosyl 12-hydroxyjasmonic acid; C494598:glucosyl jasmonate