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从红树林来源真菌 SYSU-MS0024 中分离得到的生物活性生物碱。

Bioactive Alkaloids from the Mangrove-Derived Fungus SYSU-MS0024.

机构信息

Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, Guangdong Province Engineering Laboratory for Marine Biological Products, Guangdong Provincial Engineering Technology Research Center of Seafood, Key Laboratory of Advanced Processing of Aquatic Product of Guangdong Higher Education Institution, Zhanjiang Municipal Key Laboratory of Marine Drugs and Nutrition for Brain Health, Research Institute for Marine Drugs and Nutrition, College of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, China.

School of Marine Sciences, Sun Yat-sen University, Zhuhai 519000, China.

出版信息

Mar Drugs. 2024 May 9;22(5):214. doi: 10.3390/md22050214.

Abstract

Chemical investigation of marine fungus SYSU-MS0024 cultured on solid-rice medium led to the isolation of three new alkaloids, including a pair of epimers, nigrosporines A () and B (), and a pair of enantiomers, (+)-nigrosporine C (+)-, and (-)-nigrosporine C (-)-, together with eight known compounds (-). Their structures were elucidated based on extensive mass spectrometry (MS) and 1D/2D nuclear magnetic resonance (NMR) spectroscopic analyses and compared with data in the literature. The absolute configurations of compounds - were determined by a combination of electronic circular dichroism (ECD) calculations, Mosher's method, and X-ray single-crystal diffraction technique using Cu Kα radiation. In bioassays, compound exhibited moderate inhibition on NO accumulation induced by lipopolysaccharide (LPS) on BV-2 cells in a dose-dependent manner at 20, 50, and 100 μmol/L and without cytotoxicity in a concentration of 100.0 μmol/L. Moreover, compound also showed moderate acetylcholinesterase (AChE) inhibitory activities with IC values of 103.7 μmol/L. Compound exhibited moderate antioxidant activity with EC values of 167.0 μmol/L.

摘要

从固态大米培养基中培养的海洋真菌 SYSU-MS0024 的化学研究导致分离出三种新的生物碱,包括一对差向异构体,即 nigrosporines A () 和 B (),以及一对对映异构体,(+) - nigrosporine C (+)-和 (-)-nigrosporine C (-)-,以及八种已知化合物 (-)。基于广泛的质谱 (MS) 和 1D/2D 核磁共振 (NMR) 光谱分析以及与文献数据的比较,确定了它们的结构。通过电子圆二色性 (ECD) 计算、Mosher 法和 X 射线单晶衍射技术的组合,使用 Cu Kα 辐射,确定了化合物 - 的绝对构型。在生物测定中,化合物在 20、50 和 100 μmol/L 时,以剂量依赖的方式对 LPS 诱导的 BV-2 细胞中 NO 积累表现出适度的抑制作用,且在 100.0 μmol/L 浓度下无细胞毒性。此外,化合物还表现出中等强度的乙酰胆碱酯酶 (AChE) 抑制活性,IC 值为 103.7 μmol/L。化合物表现出中等强度的抗氧化活性,EC 值为 167.0 μmol/L。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74db/11123012/bb08abb9ac8d/marinedrugs-22-00214-g001.jpg

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