biostudies-literatureWang LNatural Science Foundation of Beijing MunicipalityFundamental Research Funds for the Central UniversitiesNational Natural Science Foundation of China754-764https://www.ebi.ac.uk/biostudies/studies/S-EPMC9979263biostudies-literatureUnknown13(2)A chemical investigation on the aqueous extract of Corydalis yanhusuo tubers led to the isolation and structural elucidation of three pairs of trace enantiomeric hetero-dimeric alkaloids, (+)/(-)-yanhusamides A-C (1-3), featuring an unprecedented 3,8-diazatricylco[5.2.2.02,6]undecane-8,10-diene bridged system. Their structures were exhaustively characterized by X-ray diffraction, comprehensive spectroscopic data analysis, and computational methods. Guided by the hypothetical biosynthetic pathway for 1-3, a gram-scale biomimetic synthesis of (±)-1 was achieved in 3 steps using photoenolization/Diels-Alder (PEDA) [4+2] cycloaddition. Compounds 1‒3 exhibited potent inhibition of NO production induced by LPS in RAW264.7 macrophages. The in vivo assay showed that oral administration of 30 mg/kg of (±)-1 attenuated the severity of rat adjuvant-induced arthritis (AIA). Additionally, (±)-1 induced a dose-dependent antinociceptive effect in the acetic acid-induced mice writhing assay.Acta pharmaceutica Sinica. B(+)/(-)-Yanhusamides A-C, three pairs of unprecedented benzylisoquinoline-pyrrole hetero-dimeric alkaloid enantiomers from Corydalis yanhusuo.PMC9979263JQ18026820739782022-JYB-JBZR-015Xia HLin SWei XWang YXia GWang Lfalse(+)/(-)-Yanhusamides A-C, three pairs of unprecedented benzylisoquinoline-pyrrole hetero-dimeric alkaloid enantiomers from Corydalis yanhusuo.A chemical investigation on the aqueous extract of Corydalis yanhusuo tubers led to the isolation and structural elucidation of three pairs of trace enantiomeric hetero-dimeric alkaloids, (+)/(-)-yanhusamides A-C (1-3), featuring an unprecedented 3,8-diazatricylco[5.2.2.02,6]undecane-8,10-diene bridged system. Their structures were exhaustively characterized by X-ray diffraction, comprehensive spectroscopic data analysis, and computational methods. Guided by the hypothetical biosynthetic pathway for 1-3, a gram-scale biomimetic synthesis of (±)-1 was achieved in 3 steps using photoenolization/Diels-Alder (PEDA) [4+2] cycloaddition. Compounds 1‒3 exhibited potent inhibition of NO production induced by LPS in RAW264.7 macrophages. The in vivo assay showed that oral administration of 30 mg/kg of (±)-1 attenuated the severity of rat adjuvant-induced arthritis (AIA). Additionally, (±)-1 induced a dose-dependent antinociceptive effect in the acetic acid-induced mice writhing assay.2023-01-01T00:00:00Z2023 Feb2026-03-17T15:25:02.462Z2025-08-16T03:06:24.081ZS-EPMC99792633687318610.1016/j.apsb.2022.10.025