Cadinane-type sesquiterpenoid dimeric diastereomers hibisceusones A-C from infected stems of Hibiscus tiliaceus with cytotoxic activity against triple-negative breast cancer cells

IF 4.5 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2022-10-01 DOI:10.1016/j.bioorg.2022.105982

De-Li Chen , Guo-Xu Ma , Er-Lan Yang , Yun Yang , Can-Hong Wang , Zhao-Cui Sun , Han-Qiao Liang , Xu-Dong Xu , Jian-He Wei

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引用次数: 2

Abstract

Three new cadinane-type sesquiterpenoid dimeric diastereomers (1–3) named hibisceusones A-C were obtained from the infected stems of Hibiscus tiliaceus. The structures were determined by NMR spectroscopy and MS techniques, and the absolute configurations were assigned by ECD and single-crystal X-ray diffraction techniques. Compounds 1–3 are diastereomers, and contain a 1,4-dioxane ring linearly fused to different cadinane-type polycyclic skeletons. This is the first time that such a structure has been identified in natural products. Compounds 1–3 exhibited cytotoxic activities, and 2 showed a significantly high anti-triple-negative breast cancer (TNBC) effect. The anti-cancer effect of compound 2 was 3–4 fold higher than that of 1 and 3. The anti-cancer effect was generated via the induction of the apoptosis of the MDA-MB-231 cells by inhibiting the PI3Kα pathway.

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从感染的木槿茎中提取的对三阴性乳腺癌细胞具有细胞毒活性的cadine型倍半萜二聚体二对映体hibisceusones A-C

从木槿(hibisceusones)侵染茎中分离得到3个新的苯甲酸型倍半萜类二聚体(1-3)，命名为hibisceusones A-C。通过核磁共振光谱和质谱技术确定了结构，通过ECD和单晶x射线衍射技术确定了绝对构型。化合物1 - 3为非对映体，含有一个1,4-二氧六环，与不同的苯甲酸型多环骨架线性融合。这是首次在天然产物中发现这种结构。化合物1 ~ 3具有细胞毒活性，化合物2具有显著的抗三阴性乳腺癌(TNBC)作用。化合物2的抗癌效果是化合物1和化合物3的3 - 4倍。其抗癌作用是通过抑制PI3Kα通路诱导MDA-MB-231细胞凋亡而产生的。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.