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来自牡丹(Paeonia suffruticosa Andrews)蒴果具有强细胞毒性的芪类化合物。

Stilbenes with potent cytotoxicity from the seedcases of Paeonia suffruticosa Andrews.

作者信息

Yang Meng-Yue, Shao Zhao-Xiang, Wang Yue-Tong, Hou Yong-Lian, Zhu Ding-Kang, Chen Sha, Zhang Ya-Hui, Cao Fei, Jing Yong-Kui, Lin Bin, Li Zhan-Lin, Li Da-Hong, Hua Hui-Ming

机构信息

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, PR China.

Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.

出版信息

Phytochemistry. 2023 Jan;205:113515. doi: 10.1016/j.phytochem.2022.113515. Epub 2022 Nov 17.

Abstract

Stilbenes (based on the 1,2-diphenylethylene skeleton) are a class of plant polyphenols with rich structural and bioactive diversity. Twenty-six stilbenes, including five undescribed compounds (7,8-dioxy-4,3',5'-trihydroxystilbene, trans-13'-methoxygnetin H, suffruticosol E, paestibenetrimerols A and B), were isolated from the seedcases of Paeonia suffruticosa Andrews. Their structures were elucidated by spectroscopic analyses and comparison with previously reported data. The absolute configurations of trans-13'-methoxygnetin H, suffruticosol E, paestibenetrimerols A and B were assigned from their respective electronic circular dichroism (ECD) spectra. Additionally, the structures of known compounds suffruticosols A, B and rockiol B were revised and the absolute configurations of them, and along with (+)-davidiol A, were also further determined by ECD. The isolated compounds, trans-gnetin H, cis-gnetin H and suffruticosol E, were found to have potent cytotoxicity against the DU-145 and MDA-MB-231 cell lines with IC values of 4.89-8.61 μM. The preliminary antitumor structure-activity relationship of these stilbenes is discussed as well.

摘要

芪类化合物(基于1,2 - 二苯乙烯骨架)是一类具有丰富结构和生物活性多样性的植物多酚。从牡丹(Paeonia suffruticosa Andrews)的种皮中分离出了26种芪类化合物,包括5种未描述的化合物(7,8 - 二氧基 - 4,3',5' - 三羟基芪、反式 - 13' - 甲氧基gnetin H、suffruticosol E、paestibenetrimerols A和B)。通过光谱分析并与先前报道的数据进行比较来阐明它们的结构。反式 - 13' - 甲氧基gnetin H、suffruticosol E、paestibenetrimerols A和B的绝对构型通过各自的电子圆二色光谱(ECD)确定。此外,对已知化合物suffruticosols A、B和rockiol B的结构进行了修正,并且它们以及(+)-davidiol A的绝对构型也通过ECD进一步确定。发现分离出的化合物反式gnetin H、顺式gnetin H和suffruticosol E对DU - 145和MDA - MB - 231细胞系具有较强的细胞毒性,IC值为4.89 - 8.61 μM。还讨论了这些芪类化合物初步的抗肿瘤构效关系。

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