Quinoline alkaloids with anti-inflammatory activity from Zanthoxylum avicennae?
Organic & Biomolecular Chemistry Pub Date: 2022-05-10 DOI: 10.1039/D2OB00711H
Abstract
Zanthoxylum avicennae fruits were traditionally used to treat many inflammatory-related diseases, such as icterohepatitis, nephritis and colitis, which inspired us to explore the active chemicals and pharmacological activity. As a result, ten quinoline alkaloids, including six new ones, avicenines A–F (1–6), were isolated and structurally characterized by solid data. Compounds 1, 7 and 8 were identified as three pairs of enantiomers by chiral HPLC separation, of which 1 was an unusual 6/6/5/5-fused quinoline alkaloid bearing a unique cis-hexahydrofuro[3,2-b]furan moiety. The putative biosynthetic pathway for enantiomeric compounds was also proposed. In addition, compound 6 significantly suppressed the gene expression and secretion of pro-inflammatory cytokines IL-1β and IL-6 in macrophages.
Recommended Literature
- [1] Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France) Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique DesoeuvreEnviron. Sci.: Processes Impacts, 2013,15, 1536-1544 10.1039/C3EM00215B
- [2] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
- [3] Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent? Yukiya KitayamaPolym. Chem., 2014,5, 2784-2792 10.1039/C3PY01539D
- [4] Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling?? Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang ChiJ. Mater. Chem. A, 2021,9, 2111-2119 10.1039/D0TA07814J
- [5] Embedding heteroatoms: an effective approach to create porphyrin-based functional materials Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro OsukaDalton Trans., 2017,46, 13322-13341 10.1039/C7DT02815F
- [6] Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes? Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. ParkinJ. Mater. Chem. A, 2020,8, 22075-22082 10.1039/D0TA08638J
- [7] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [8] Excitable dynamics in the bromate–sulfite–ferrocyanide reaction J. Zagora,M. Vosla?,L. Schreiberová,I. SchreiberPhys. Chem. Chem. Phys., 2002,4, 1284-1291 10.1039/B110048C
- [9] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
- [10] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)