Daphmacrimines A−K, Daphniphyllum alkaloids from Daphniphyllum macropodum Miq

Daphmacrimines A–K (1–11) were isolated from the leaves and stems of Daphniphyllum macropodum Miq. Their structures and stereochemistries were determined by extensive techniques, including HRESIMS, NMR, ECD, IR, and single-crystal X-ray crystallography. Daphmacrimines A–D (1–4) are unprecedented Daphniphyllum alkaloids with a 2-oxazolidinone ring. Daphmacrimine I (9) contains a nitrile group, which is relatively rare in naturally occurring alkaloids. The abilities of daphmacrimines A–D and daphmacrimines G–K to enhance lysosomal biogenesis were evaluated through LysoTracker Red staining. Daphmacrimine K (11) can induce lysosomal biogenesis and promote autophagic flux. Eleven previously undescribed Daphniphyllum alkaloids daphmacrimines A–K (1–11), were isolated from the leaves and stems of Daphniphyllum macropodum Miq. Daphmacrimines A–D (1–4) were unprecedented Daphniphyllum alkaloids with a 2-oxazolidinone ring. Daphmacrimine I (9) contains a nitrile group which is relatively rare in naturally occurring alkaloids. Furthermore, the abilities of daphmacrimines A–D (1–4) and daphmacrimines G–K (7–11) to enhance lysosomal biogenesis were evaluated through LysoTracker Red staining. Daphmacrimine K (11) could induce lysosomal biogenesis and promote autophagic flux. [Display omitted] •Eleven undescribed Daphniphyllum alkaloids were isolated from the leaves and stems of Daphniphyllum macropodum Miq.•Daphmacrimines A–D (1–4) were unprecedented Daphniphyllum alkaloids with a 2-oxazolidinone ring.•Daphmacrimine I (9) contains a nitrile group which is relatively rare in naturally occurring alkaloids.•Daphmacrimine K (11) could induce lysosomal biogenesis and promote autophagic flux.