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),...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[5.2.2.0^(2,6)]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.展开更多
基金supported by the National Natural Science Foundation of China(No.82073978)Beijing Natural Science Foundation(No.JQ18026,China)the Fundamental Research Funds for the Central Universities(2022-JYB-JBZR-015,China)。
文摘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[5.2.2.0^(2,6)]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.
