title: Design and synthesis of aloe-emodin derivatives as potent anti-tyrosinase, antibacterial and anti-inflammatory agents.
abstract: Twenty aloe-emodin derivatives were designed, synthesized, and their biological activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, compounds with thiosemicarbazide moiety showed more potent inhibitory effects than the other compounds. The structure-activity relationships (SARs) were preliminarily discussed. The inhibition mechanism of selected compounds 1 and 13 were investigated. The results showed compound 1 was reversible inhibitor, however, compound 13 was irreversible. Kinetic analysis indicated that compound 1 was competitive tyrosinase inhibitor. Furthermore, the antibacterial activities and anti-inflammatory activities of some selected compounds were also screened. The results showed that compound 3 exhibited more potent antibacterial activity than the aloe-emodin, compounds 5 and 6 possessed more potent anti-inflammatory activities than the diacerein.
authors.affiliation: Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, China. Electronic address: syuliujb@163.com.
authors.forename: Jinbing
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, China.
authors.forename: Fengyan
authors.initials: F
authors.lastname: Wu
authors.affiliation: Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, China.
authors.forename: Changhong
authors.initials: C
authors.lastname: Chen
mesh_terms: D000363:Agaricales; D000818:Animals; D000880:Anthraquinones / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology*; D004642:Emodin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D011753:Pyrones / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D011753:Pyrones; C025292:diacerein; C011890:kojic acid; D014442:Monophenol Monooxygenase; D004642:Emodin
keywords: Aloe-emodin derivatives; Anti-inflammatory activity; Antibacterial activity; Tyrosinase inhibitory activities