63992-22-3Relevant articles and documents
Strigolactones: A plant phytohormone as novel anti-inflammatory agents
Zheng, Jun-Xia,Han, Yu-Shui,Wang, Jin-Cai,Yang, Hui,Kong, Hao,Liu, Kang-Jia,Chen, Si-Yu,Chen, Yi-Rui,Chang, Yi-Qun,Chen, Wei-Min,Guo, Jia-Liang,Sun, Ping-Hua
, p. 181 - 188 (2018)
Strigolactones (SLs) are a novel class of plant hormones with enormous potential for the prevention and treatment of inflammation. To further investigate the anti-inflammatory activities of SLs, a representative SL, GR24, and the reductive products of its D-ring were synthesized and their anti-inflammatory activities were fully evaluated on both in vitro and in vivo models. Among these compounds, the two most active optical isomers (2a and 6a) demonstrated strong inhibitory activity on the release of inflammatory cytokines, including nitric oxide (NO), tumor necrosis factor-alpha (TNF-α), and interleukin-6 (IL-6) by blocking the nuclear factor kappa B (NF-κB) and mitogen-activated protein kinase (MAPK) signaling pathways; they also greatly inhibited the migration of neutrophils and macrophages in fluorescent protein labeled zebrafish larvae. These results identified the promising anti-inflammatory effects of SLs, and suggested that both the absolute configuration of SL and the α,β-unsaturated D-ring structure are essential for the observed anti-inflammatory activity.
A new efficient synthesis of GR24 and dimethyl A-ring analogues, germinating agents for seeds of the parasitic weeds Striga and Orobanche spp.
Malik, Heetika,Rutjes, Floris P.J.T.,Zwanenburg, Binne
experimental part, p. 7198 - 7203 (2010/10/02)
An efficient and high yielding preparation for the synthetic germination stimulant GR24 (5) and its A-ring dimethyl-substituted analogues 30-32 has been described. The first step involves a Stobbe condensation of benzaldehydes 9-11 with dimethyl succinate. Subsequent transposition of the ester and reduction of the double bond provides the building blocks 15-17 for an intramolecular Friedel-Crafts acylation. ABC-lactones 22-25 are prepared from γ-keto esters 18-21 by saponification, subsequent reduction with sodium borohydride followed by acid-catalyzed lactonization. Coupling of the lactones with the D-ring is accomplished by formylation and subsequent treatment with bromobutenolide 8 to give GR24 and its dimethyl analogues. Bioassays with Striga hermonthica seeds reveal that the dimethyl analogues are slightly less active than GR24 itself.
The Preparation of Synthetic Analogues of Strigol
Johnson, Alan W.,Gowda, Gopala,Hassanali, Ahmed,Knox, John,Monaco, Sam,et al.
, p. 1734 - 1743 (2007/10/02)
A range of analogues of the natural germination stimulant, strigol, for parasitic weeds of the genera Striga and Orobanche, has been prepared.Most of the products contain an α-formyl-γ-lactone (or α-formyl-γ-lactam) grouping attached through an enol-ether linkage to the 5-position of a but-2-enolide.Some have shown sufficiently high activities as to warrant large-scale field trials.
