Daphmacrimines A-K, Daphniphyllum alkaloids from Daphniphyllum macropodum Miq

Li-Li Xu; Zhen-Peng Niu; Duo-Zhi Chen; Yu Zhang; Qian Zhao; Hong Liang; Sheng Li; Jin-Liang Li; Xiao Ding; Chong-Lin Yang; Xiao-Jiang Hao

doi:10.1016/j.phytochem.2024.114106

Daphmacrimines A-K, Daphniphyllum alkaloids from Daphniphyllum macropodum Miq

Phytochemistry. 2024 Apr 23:223:114106. doi: 10.1016/j.phytochem.2024.114106. Online ahead of print.

Authors

Li-Li Xu¹, Zhen-Peng Niu², Duo-Zhi Chen², Yu Zhang³, Qian Zhao⁴, Hong Liang², Sheng Li³, Jin-Liang Li³, Xiao Ding⁵, Chong-Lin Yang⁶, Xiao-Jiang Hao⁷

Affiliations

¹ Center for Life Sciences, School of Life Sciences, Yunnan University, Kunming, 650091, China; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China; Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China; Research Unit of Chemical Biology of Natural Anti-Virus Products, Chinese Academy of Medical Sciences, Beijing, 100730, China. Electronic address: dingxiao@mail.kib.ac.cn.
⁶ Center for Life Sciences, School of Life Sciences, Yunnan University, Kunming, 650091, China. Electronic address: clyang@ynu.edu.cn.
⁷ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China; Research Unit of Chemical Biology of Natural Anti-Virus Products, Chinese Academy of Medical Sciences, Beijing, 100730, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming, 650106, China. Electronic address: haoxj@mail.kib.ac.cn.

PMID: 38657885
DOI: 10.1016/j.phytochem.2024.114106

Abstract

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.

Keywords: Daphniphyllaceae; Daphniphyllum alkaloids; Daphniphyllum macropodum miq.; Lysosomal biogenesis; Structural elucidation.