Статья

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

Li XiangState Key Laboratory of Drug ResearchJishan QinShanghai Institute of Materia Medica, Chinese Academy of SciencesTemur A. KushatovDepartment of Organic Synthesis and Bioorganic Chemistry, Institute of BiochemistryFirdavsi TursunovDepartment of Organic Synthesis and Bioorganic Chemistry, Institute of BiochemistryOzod FarmonovShanghai Institute of Materia Medica, Chinese Academy of SciencesXiangrui JiangBohai Rim Advanced Research Institute for Drug DiscoveryFeipu YangShanghai Institute of Materia Medica, Chinese Academy of SciencesJingshan ShenShanghai Institute of Materia Medica, Chinese Academy of SciencesKhurshed BozorovDepartment of Organic Synthesis and Bioorganic Chemistry, Institute of BiochemistryHaji Akber AisaSchool of Pharmacy

Journal of Natural Productsjournal2025en

ABI

Аннотация

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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Темы

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

Идентификаторы

DOI: 10.1021/acs.jnatprod.5c01211

Цитирования и источники

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