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Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates

Li XiangShanghai Institute of Materia Medica, Chinese Academy of SciencesJishan QinState Key Laboratory of Drug ResearchTemur A. KushatovSamarkand State UniversityFirdavsi TursunovSamarkand State UniversityOzod FarmonovState Key Laboratory of Drug ResearchXiangrui JiangBohai Rim Advanced Research Institute for Drug DiscoveryFeipu YangShanghai Institute of Materia Medica, Chinese Academy of SciencesJingshan ShenUniversity of Chinese Academy of SciencesKhurshed BozorovSamarkand State UniversityHaji Akber AisaXinjiang Medical University

Journal of Natural Productsjournal2025en

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ABI

Annotatsiya

The first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (1a) and oxyacanthine (1b) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for macrocycle formation. Our synthesis unequivocally confirmed the sample misidentification of 1a, as indicated in our previous work. Evaluation of anti-inflammatory activities revealed that both synthetic and natural berbamine or oxyacanthine comparably suppressed gene expression of pro-inflammatory cytokines IL-6 and IL-1β in LPS-stimulated RAW 264.7 macrophages. Notably, intermediate 15a displayed potent anti-inflammatory activity coupled with minimal cytotoxicity, emerging as a promising lead candidate for the development of novel anti-inflammatory agents.

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Mavzular

Berberine and alkaloids research Ziziphus Jujuba Studies and Applications Traditional and Medicinal Uses of Annonaceae

Identifikatorlar

DOI: 10.1021/acs.jnatprod.5c01211

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