title: Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities.
abstract: A series of isoquinoline alkaloids including tetrahydroprotoberberines, N-methyl tetrahydroprotoberberines and protoberberines were facile synthesised with protopines as the starting material. All compounds were evaluated for their antibacterial activities against four pathogenic bacteria Escherichia coli, Staphyloccocus aureus, Staphylococcus gallinarum and Salmonella choleraesuis. Experimental results indicated that protoberberines were the most active compounds to the target bacteria among the tested alkaloids. It was suggested that planar molecule with high aromatisation level (e.g. coptisine 5 and berberine 6) or a positive charge of the molecules (e.g. N-methyl tetrahydroprotoberberines 11 and 12) had a positive influence on the antibacterial effects.
authors.affiliation: a Pre-State Key Laboratory for Germplasm Innovation and Utilization of Crop , Hunan Agricultural University , Changsha , Hunan 410128 , P.R. China.
authors.forename: Pi
authors.initials: P
authors.lastname: Cheng
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.forename: Xiubin
authors.initials: X
authors.lastname: Liu
authors.forename: Wei
authors.initials: W
authors.lastname: Liu
authors.forename: Weisong
authors.initials: W
authors.lastname: Kang
authors.forename: Jie
authors.initials: J
authors.lastname: Zhou
authors.forename: Jianguo
authors.initials: J
authors.lastname: Zeng
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D053119:Benzophenanthridines / Q000737:chemistry*; D001599:Berberine / Q000031:analogs & derivatives / Q000737:chemistry; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013210:Staphylococcus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D007546:Isoquinolines; C034384:coptisine; D001599:Berberine; C009093:protopine