Novel Oleanane-Type Triterpene Glycosides from the <i>Saponaria officinalis</i> L. Seeds and Apoptosis-Inducing Activity via Mitochondria

Novel Oleanane-Type Triterpene Glycosides from the <i>Saponaria officinalis</i> L. Seeds and Apoptosis-Inducing Activity via Mitochondria

<i>Saponaria officinalis</i> L., commonly known as “Soapwort”, is a rich source of triterpene glycosides; however, the chemical constituents of <i>S. officinalis</i> seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of...

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Bibliographic Details
Main Authors: Naoki Takahashi, Tomoki Iguchi, Minpei Kuroda, Masaki Mishima, Yoshihiro Mimaki
Format: Article
Language:English
Published: MDPI AG 2022-02-01
Series:International Journal of Molecular Sciences
Subjects:
<i>Saponaria officinalis</i>
Caryophyllaceae
seed
triterpene glycoside
cytotoxicity
apoptosis
Online Access:https://www.mdpi.com/1422-0067/23/4/2047
Description
Summary:<i>Saponaria officinalis</i> L., commonly known as “Soapwort”, is a rich source of triterpene glycosides; however, the chemical constituents of <i>S. officinalis</i> seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of <i>S. officinalis</i> and obtained 17 oleanane-type triterpene glycosides (<b>1</b>–<b>17</b>), including seven new glycosides (<b>1</b>–<b>7</b>). The structures of <b>1</b>–<b>7</b> 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 <b>1</b>, <b>4</b>, and <b>10</b> toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound <b>1</b>, a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G<sub>2</sub>/M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by <b>1</b>, mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells.
ISSN:1661-6596
1422-0067

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