title: Synthesis, photostability and bioactivity of 2,3-cyclopropanated abscisic acid.
abstract: The plant hormone abscisic acid (ABA) plays a central role in the regulation of plant development and adaptation to environmental stress. The isomerization of ABA to the biologically inactive 2E-isomer by light considerably limits its applications in agricultural fields. To overcome this shortcoming, an ABA analogue, cis-2,3-cyclopropanated ABA, was synthesized, and its photostability and biological activities were investigated. This compound showed high photostability under UV light exposure, which was 4-fold higher than that of (±)-ABA. cis-2,3-cyclopropanated ABA exhibited high ABA-like activity, including the ability to effectively inhibit seed germination, seedling growth and stomatal movements of Arabidopsis. In some cases, its bioactivity approaches that of (±)-ABA. trans-2,3-cyclopropanated abscisic acid was also prepared, an isomer that was more photostable but which showed weak ABA-like activity.
authors.affiliation: College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Liu
authors.initials: L
authors.lastname: Wenjian
authors.forename: Han
authors.initials: H
authors.lastname: Xiaoqiang
authors.forename: Xiao
authors.initials: X
authors.lastname: Yumei
authors.forename: Fan
authors.initials: F
authors.lastname: Jinlong
authors.forename: Zhang
authors.initials: Z
authors.lastname: Yuanzhi
authors.forename: Lu
authors.initials: L
authors.lastname: Huizhe
authors.forename: Wang
authors.initials: W
authors.lastname: Mingan
authors.forename: Qin
authors.initials: Q
authors.lastname: Zhaohai
mesh_terms: D000040:Abscisic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000235:genetics / Q000494:pharmacology; D017360:Arabidopsis / Q000235:genetics / Q000254:growth & development / Q000378:metabolism; D003521:Cyclopropanes / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D015394:Molecular Structure; D000081222:Monocyclic Sesquiterpenes; D019906:Nuclear Magnetic Resonance, Biomolecular; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: C000588996:2,3-cyclopropanated abscisic acid; D003521:Cyclopropanes; D000081222:Monocyclic Sesquiterpenes; D000040:Abscisic Acid
keywords: Abscisic acid; Arabidopsis thaliana; Bioactivity; Cruciferae; Photostability; Synthesis; cis-2,3-Cyclopropanated ABA