1. Novel Oleanane-Type Triterpene Glycosides from the Saponaria officinalis L. Seeds and Apoptosis-Inducing Activity via Mitochondria.
- Author
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Takahashi N, Iguchi T, Kuroda M, Mishima M, and Mimaki Y
- Subjects
- A549 Cells, Cell Cycle drug effects, Humans, Oleanolic Acid metabolism, Saponaria metabolism, Seeds chemistry, Seeds metabolism, Antineoplastic Agents toxicity, Apoptosis, Mitochondria metabolism, Oleanolic Acid toxicity, Saponaria chemistry
- Abstract
Saponaria officinalis L., commonly known as "Soapwort", is a rich source of triterpene glycosides; however, the chemical constituents of S. officinalis seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of S. officinalis and obtained 17 oleanane-type triterpene glycosides ( 1 - 17 ), including seven new glycosides ( 1 - 7 ). The structures of 1 - 7 were determined based on a detailed analysis of NMR spectroscopic data and chromatographic and spectroscopic analyses following specific chemical transformation. The cytotoxicities of the isolated compounds were evaluated against HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells. The cytotoxicities of 1 , 4 , and 10 toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound 1 , a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G
2 /M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by 1 , mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells.- Published
- 2022
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