Improved synthetic route of exo-16,17-dihydro-gibberellin A5-13-acetate and the bioactivity of its derivatives towards Arabidopsis thaliana.

The use of exo-16,17-dihydro-gibberellin A5-13-acetate (DHGA₅ ) in agriculture has been limited by its low synthetic yield. This study was aimed at optimizing the synthetic route of DHGA₅ , designing and synthesizing new derivatives with strong plant growth inhibitory activities.

Previous synthetic methods were replaced with a shorter, milder and faster reaction route with higher yield (76.3%) of DHGA₅ . Based on this novel route, a series of new derivatives were designed and synthesized using DHGA₅ as a lead compound and characterized and evaluated for biological activities in Arabidopsis thaliana. Among the 15 tested derivatives, compound 14j showed a lower medium inhibition concentration (IC₅₀ , 73 μm) in Arabidopsis than that of DHGA₅ (91 μm). Gibberellin deficient mutant assay further revealed that 14j had very different activities compared to DHGA₅ as it specifically inhibits gibberellin biosynthetic pathways. In addition, 14j does not influence the interaction between gibberellin receptors (GID1) and the master growth repressor (RGA) based on yeast two-hybrid assay.

The optimized synthetic route provides a promising method for large-scale preparation of DHGA₅ . Our biological assays indicate that 14j likely acts on gibberellin signaling elements other than GID1. These results indicate that novel plant growth regulators can be developed. © 2019 Society of Chemical Industry.