Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI

Liu Mengting; Zhou Qun; Wang Jianping; Liu Junjun; Qi Changxing; Lai Yongji; Zhu Hucheng; Xue Yongbo; Hu Zhengxi; Zhang Yonghui

首页> 外文期刊>RSC Advances >Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI

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Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI

机译：来自珊瑚衍生的真菌的抗炎丁烯酯衍生物，曲霉属叶绿素D和G，丁内酯VI和4,8-二乙酰丁内酯VI的结构修订

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Chemical investigation of the coral-derived fungus Aspergillus terreus led to the discovery of ten butenolide derivatives (1-10), including four new ones (1-4). The new structures were characterized on the basis of comprehensive spectroscopic analysis, including 1D and 2D NMR and HRESIMS data. Compounds 1 and 2 were a pair of rare C-8 epimers with vicinal diol motifs. The absolute configurations of 1-4 were determined via [Mo-2(AcO)(4)] induced circular dichroism (ICD) spectra and comparison of their experimental ECD spectra. Importantly, the structures of reported aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI have been correspondingly revised via a combined strategy of experimental validations, C-13 NMR predictions by ACD/Labs software, and C-13 NMR calculations. Herein we provide valuable referenced C-13 NMR data (C-7, C-8, and C-9) for the structure elucidations of butenolide derivatives with 1-(2-hydroxyphenyl)-3-methylbutane-2,3-diol, 2-(2,3-dihydrobenzofuran-2-yl)propan-2-ol, or 2,2-dimethylchroman-3-ol motifs. Additionally, all the isolates (1-10) were assessed for anti-inflammatory activity by measuring the amount of NO production in lipopolysaccharide (LPS)-induced RAW 264.7 mouse macrophages, and compound 10 showed an even stronger inhibitory effect than the postive control indomethacin, presenting it as a promising lead compound for the development of new anti-inflammatory agents.

机译：珊瑚衍生的真菌的化学研究导致了十种丁醇钠衍生物（1-10）的发现，包括四个新（1-4）。新结构的特征在于综合光谱分析，包括1D和2D NMR和HRESIMS数据。化合物1和2是含有邻甲基二醇基序的一对稀有的C-8个基础。通过[Mo-2（ACO）（4）]诱导的圆形二色性（ICD）光谱和其实验ECD光谱比较确定1-4的绝对配置。重要的是，通过ACD / Labs软件的实验验证C-13 NMR预测和C-13 NMR计算的组合策略，对报告的曲脂糖苷D和G，丁内酯VI和4,8-二乙酰丁内酯VI的结构已相应地修订，C-13 NMR预测和C-13 NMR计算。在此，我们提供有价值的C-13 NMR数据（C-13 NMR数据（C-7，C-8和C-9），用于用1-（2-羟基苯基）-3-甲基丁烷-2,3-二醇的丁醇钠衍生物的结构阐明， 2-（2,3-二氢呋喃脲-2-基）Propan-2-OL，或2,2-二甲基核 - 3-OL主题。另外，通过测量脂多糖（LPS）诱导的未生产的生产量来评估所有分离物（1-10）的抗炎活性，诱导的原料264.7小鼠巨噬细胞，化合物10显示出比垂直控制吲哚美辛的肿瘤效果更强，将其作为开发新的抗炎剂的有前途的铅化合物。

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《RSC Advances》 |2018年第23期|共8页
作者
Liu Mengting; Zhou Qun; Wang Jianping; Liu Junjun; Qi Changxing; Lai Yongji; Zhu Hucheng; Xue Yongbo; Hu Zhengxi; Zhang Yonghui;
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Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Cent Hosp Wuhan Dept Pharm Wuhan 430014 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

Huazhong Univ Sci &

Technol Tongji Med Coll Sch Pharm Hubei Key Lab Nat Med Chem &

Resource Evaluat Wuhan 430030 Hubei Peoples R China;

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1. Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI [J] . Liu Mengting, Zhou Qun, Wang Jianping, RSC Advances . 2018,第23期

机译：来自珊瑚衍生的真菌的抗炎丁烯酯衍生物，曲霉属叶绿素D和G，丁内酯VI和4,8-二乙酰丁内酯VI的结构修订
2. Butyrolactone-I from Coral-Derived Fungus Aspergillus terreus Attenuates Neuro-Inflammatory Response via Suppression of NF-κB Pathway in BV-2 Cells [J] . Yuan Yuan Zhang, Yi Zhang, Yuan-Bei Yao, Marine Drugs . 2018,第6期

机译：珊瑚来源的真菌曲霉曲霉的丁内酯-I通过抑制BV-2细胞中的NF-κB通路来减轻神经炎症反应。
3. Structures and Antiviral Activities of Butyrolactone Derivatives Isolated from Aspergillus terreus MXH-23 [J] . MA Xinhua, ZHU Tianjiao, GU Qianqun, 中国海洋大学学报（英文版） . 2014,第006期

机译：从土壤曲霉MXH-23分离丁内酯衍生物的结构和抗病毒活性。
4. Phase Behavior and Solvation of Lithium Triflate in γ-Butyrolactone [C] . M. P. Foley, D. M. Seo, P. D. Boyle, Symposium on grahame award symposium and physical and analytical electrochemistry general session;Meeting of the Electrochemical Society . 2012

机译：三氟甲磺酸锂在γ-丁内酯中的相行为和溶剂化
5. Synthesis of C2 symmetric cyclobutanes and gamma-butyrolactones via photoinduced electron transfer. [D] . Riener, Michelle. 2014

机译：通过光致电子转移合成C2对称环丁烷和γ-丁内酯。
6. Butyrolactone-I from Coral-Derived Fungus Aspergillus terreus Attenuates Neuro-Inflammatory Response via Suppression of NF-κB Pathway in BV-2 Cells [O] . Yuan Yuan Zhang, Yi Zhang, Yuan-Bei Yao, 2018

机译：珊瑚来源的真菌曲霉曲霉的丁内酯-I通过抑制BV-2细胞中的NF-κB通路来减轻神经炎症反应。
7. Territrem and Butyrolactone Derivatives from a Marine-Derived Fungus Aspergillus Terreus [O] . Xu-Hua Nong, Yi-Fei Wang, Xiao-Yong Zhang, 2014

机译：来自海洋衍生真菌aspergillus Terreus的Territrem和丁内酯衍生物

Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4,8-diacetoxy butyrolactone VI

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