Abstract:
:12-O-β-D-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for the FLAG-tagging of JAG target. We synthesized four hybrid-type JAG-CMP stereoisomers (7, ent-7, 8, and ent-8), which are composed of (-)-12-OH-JA (2)/D-galactopyranoside, (-)-2/L-galactopyranoside, (+)-ent-2/d-galactopyranoside, and (+)-ent-2/L-galactopyranoside moieties, respectively, and we examined their biological features, such as the stereospecific induction of shrinkage, rate of the cellular response, and dependence on potassium channel activity. These features of the JAG-CMPs were completely consistent with those of the original JAG. These results indicate the biological equivalence of JAG and the JAG-CMPs. During the course of such biological evaluations, it was revealed that the biological activity of the CMPs is greatly dependent on the d/l-stereochemistry of a glycon moiety. To the best of our knowledge, this is the first study suggesting that the d/l-stereochemistry of the glycon moiety significantly affects the biological activity of the associated glycoside.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Ueda M,Yang G,Ishimaru Y,Itabashi T,Tamura S,Kiyota H,Kuwahara S,Inomata S,Shoji M,Sugai Tdoi
10.1016/j.bmc.2012.08.003subject
Has Abstractpub_date
2012-10-01 00:00:00pages
5832-43issue
19eissn
0968-0896issn
1464-3391pii
S0968-0896(12)00616-5journal_volume
20pub_type
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