Taxamairins are a subclass of highly unsaturated icetexanes ketones isolated from Taxus species with potential medicinal significance. However, collecting taxamairins from natural sources is illegal and ineffective, significantly limiting further research. The published organic total synthesis techniques to produce taxamairins have limitations for large-scale synthesis, such as protracted synthetic approaches, poor yields, impractical key steps, high costs of reagents, etc.<br/>    The natural compounds TaxA and TaxB were practically semi-synthesized from the commercially available natural product carnosic acid, which went through 6 and 7 steps, respectively, with yields of 12% and 21% in gram scales in 7 days. Additionally, 17 taxamairin analogs were created and produced for the SAR study through hydroxylation, oxidation, esterification, amidation, and coupling reactions.<br/>    According to the bioactivity experiments, taxamairins had strong anti-inflammatory effects in LPS-induced macrophages and DSS-induced acute colitis mouse models. Taxamairins inhibited LPS-induced NO production, iNOS expression, and the transcription and secretion of pro-inflammatory cytokines including IL-1β, TNF-α, and IL-6. Taxamairins also suppressed the inflammatory response and made mice less susceptible to DSS-induced colitis. The findings show that taxamairins have anti-inflammatory properties and have the potential to be used as a therapeutic agent in the treatment of IBD.

Semi-synthesis and anti-inflammatory activities evaluation of taxamairins

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