Citation: Xiang Yuan, Zhenyuan Li, Ziming Feng, Jianshuang Jiang, Yanan Yang, Peicheng Zhang. Alopecuroidines A−C, three matrine-derived alkaloids from the seeds of Sophora alopecuroides[J]. Chinese Chemical Letters, ;2021, 32(12): 4058-4062. doi: 10.1016/j.cclet.2021.04.022 shu

Alopecuroidines A−C, three matrine-derived alkaloids from the seeds of Sophora alopecuroides

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

pczhang@imm.ac.cn

Received Date: 4 February 2021
Revised Date: 5 April 2021
Accepted Date: 12 April 2021
Available Online: 23 April 2021

Figures(6)

Three matrine-derived alkaloids, alopecuroidine A (1), alopecuroidine B (2a) and alopecuroidine C (2b) were isolated from the seeds of Sophora alopecuroides. Their structures were elucidated by extensive spectroscopic analyses and X-ray diffraction. Three compounds possess an unprecedented rearranged fused 7/6/5/6 tetracyclic skeleton with a diazacycloheptane structure. Their plausible biosynthetic pathway was also proposed. The anti-proliferative activities of compounds 1 and 2a were examined by the MTT assay. Compound 1 inhibited the viability of human lung cancer A549 cells, having a half maximal inhibitory concentration (IC₅₀) of 7.58 ± 2.47 µmol/L at 72 h. The flow cytometric analysis suggested that 1 inhibited A549 cell growth by inducing apoptosis and cell-cycle arrest. Additionally, 1 induced the loss of mitochondrial membrane potential, elevated intracellular reactive oxygen species, increased the Bax/Bcl-2 ratio, stimulated cleaved-caspase-3 and P53 protein levels, and suppressed the pro-caspase-3 level. Thus, 1 appeared to induce A549 cells apoptosis through a mitochondria-mediated apoptotic pathway.
- Alkaloids,
- Sophora alopecuroides,
- X-ray diffraction,
- Anti-proliferative,
- Apoptosis
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沈阳化工大学材料科学与工程学院沈阳 110142