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(±)-Hypernumqulins A–H: Eight pairs of unexpected [2+2] cycloaddition sesquiterpenoid alkaloid with 6/6/6/4/10 ring system from Hypericum monogynum L.
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2024-06-14 , DOI: 10.1016/j.bioorg.2024.107564 Zhaoyue Dong 1 , Qingxiu Pu 2 , Yinda Qiu 2 , Ruifeng Zhang 2 , Qianyu Chen 2 , Qingju Liu 2 , Ammara Khalid 2 , Fancheng Meng 2 , Guowei Wang 2 , Zhihua Liao 3 , Min Chen 1
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2024-06-14 , DOI: 10.1016/j.bioorg.2024.107564 Zhaoyue Dong 1 , Qingxiu Pu 2 , Yinda Qiu 2 , Ruifeng Zhang 2 , Qianyu Chen 2 , Qingju Liu 2 , Ammara Khalid 2 , Fancheng Meng 2 , Guowei Wang 2 , Zhihua Liao 3 , Min Chen 1
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(±)-Hypernumqulins A–H (), eight pairs of enantiomeric quinoline alkaloids fused with an isopentenyl and a germacrane-type sesquiterpenoid, featuring an unprecedented skeleton with 6/6/6/4/10 ring system, were isolated from L. under the guidance of molecular networking strategy. Their structures including absolute configuration were elucidated by NMR spectroscopy analysis, X-ray crystallography and quantum chemical calculation. The proposed [2+2] cycloaddition may play a key biogenic step in building the unexpected skeleton. Most of the isolates exhibited cytotoxicity with IC values ranging from 2.82 ± 0.03 to 45.25 ± 1.26 μM against MCF-7, A549 or SGC7901 cells. Furthermore, compounds (±)- and (−)- could induce apoptosis by upregulating the protein expression level of Bax and downregulating of Bcl-2 in MCF-7 cells. These findings provided the first example of germacrane sesquiterpene quinoline alkaloids, and supported the possibilities for the development of new anti-tumor agents.
中文翻译：
(±)-Hypernumqulins A–H：来自 Hypericum monogynum L 的八对意想不到的 [2+2] 环加成倍半萜生物碱，具有 6/6/6/4/10 环系统。
(±)-Hypernumqulins A–H ()是从 L.在分子网络策略的指导下。通过核磁共振波谱分析、X射线晶体学和量子化学计算阐明了它们的结构，包括绝对构型。所提出的[2+2]环加成可能在构建意想不到的骨架中发挥关键的生物发生步骤。大多数分离株对 MCF-7、A549 或 SGC7901 细胞表现出细胞毒性，IC 值范围为 2.82 ± 0.03 至 45.25 ± 1.26 μM。此外，化合物(±)-和(-)-可以通过上调MCF-7细胞中Bax蛋白表达水平并下调Bcl-2来诱导细胞凋亡。这些发现提供了吉马鹤倍半萜喹啉生物碱的第一个例子，并支持了开发新型抗肿瘤药物的可能性。
更新日期：2024-06-14
中文翻译：
(±)-Hypernumqulins A–H：来自 Hypericum monogynum L 的八对意想不到的 [2+2] 环加成倍半萜生物碱，具有 6/6/6/4/10 环系统。
(±)-Hypernumqulins A–H ()是从 L.在分子网络策略的指导下。通过核磁共振波谱分析、X射线晶体学和量子化学计算阐明了它们的结构，包括绝对构型。所提出的[2+2]环加成可能在构建意想不到的骨架中发挥关键的生物发生步骤。大多数分离株对 MCF-7、A549 或 SGC7901 细胞表现出细胞毒性，IC 值范围为 2.82 ± 0.03 至 45.25 ± 1.26 μM。此外，化合物(±)-和(-)-可以通过上调MCF-7细胞中Bax蛋白表达水平并下调Bcl-2来诱导细胞凋亡。这些发现提供了吉马鹤倍半萜喹啉生物碱的第一个例子，并支持了开发新型抗肿瘤药物的可能性。
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