Norcolocynthenins A and B, two cucurbitane 3-nor-Triterpenoids from Citrullus colocynthis and their cytotoxicity.,Bioorganic Chemistry

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Norcolocynthenins A and B, two cucurbitane 3-nor-Triterpenoids from Citrullus colocynthis and their cytotoxicity.
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2020-06-25 , DOI: 10.1016/j.bioorg.2020.104045
Yushuang Liu ₁ , Lu Zhang ₂ , Jingjing Xue ₃ , Kaibo Wang ₄ , Huiming Hua ₃ , Tao Yuan ₅

Affiliation

The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang330022, China; The Key Laboratory of Plant Resources and Chemistry of Arid Zone, State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, IN 47907, United States.
The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang330022, China.
Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, IN 47907, United States.
The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang330022, China; The Key Laboratory of Plant Resources and Chemistry of Arid Zone, State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China.

Two novel cucurbitane 3-nor-triterpenoids, named norcolocynthenins A (1) and B (2), were isolated from the fruits of Citrullus colocynthis. The structures including their absolute configurations were determined by extensive spectroscopic analyses and theoretical calculations. Compound 1 features an unprecedented 5/6/6/5-fused ring system while compound 2 possesses a rare lactone moiety at modified ring A. Compounds 1 and 2 showed significant cytotoxic activity against human cancer cell lines of HL-60 (IC₅₀ = 8.32, 6.49 μM) and PC-3 (IC₅₀ = 31.26, 13.42 μM). The plausible biosynthetic pathway of compounds 1 and 2 via a key enzymatic Baeyer-Villiger reaction is proposed.

中文翻译：

Norcolocynthenins A和B，两个瓜（Citrullus colocynthis）的葫芦烷3-nor-三萜类化合物及其细胞毒性。

两种新型葫芦3去甲三萜类化合物，命名为norcolocynthenins A（1）和B（2），从该果实中分离西瓜colocynthis。通过广泛的光谱分析和理论计算确定包括绝对构型在内的结构。化合物1具有前所未有的5/6/6/5稠合的环系统，而化合物2在修饰的环A上具有稀有的内酯部分。化合物1和2对HL-60的人类癌细胞系显示出显着的细胞毒活性（IC ₅₀ = 8.32、6.49μM）和PC-3（IC ₅₀ = 31.26，13.42μM）。化合物的合理生物合成途径提出了通过关键的酶促Baeyer-Villiger反应的图1和图2。

更新日期：2020-07-03

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