Practical Synthesis and Biological Evaluation of Bergenin Analogs

• Published in: Chemical biology & drug design Vol. 78; no. 4; pp. 725 - 729
• Main Authors: Jung, Jae-Chul, Lim, Eunyoung, Kim, Seung Hwan, Kim, Nam Soo, Jung, Mankil, Oh, Seikwan
• Format: Journal Article
• Language: English
• Published: Oxford, UK Blackwell Publishing Ltd 01.10.2011; Wiley
• Subjects: Acylation; acylation reaction; Animals; Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - pharmacology; Benzopyrans - chemical synthesis; Benzopyrans - chemistry; Benzopyrans - pharmacology; bergenin; Biochemistry & Molecular Biology; Cell Line; Chemistry Techniques, Synthetic; Chemistry, Medicinal; Life Sciences & Biomedicine; Lipopolysaccharides - metabolism; methylation; Mice; Mice, Inbred C57BL; Microglia - cytology; Morphine Dependence - drug therapy; neurotoxicity; Nitric Oxide - metabolism; NO generation; Pharmacology & Pharmacy; Science & Technology; Substance-Related Disorders; ANTIOXIDANT ACTIVITY; neurotoxicity; PHYTOCONSTITUENT; methylation; BARK; acylation reaction; bergenin; NO generation; DERIVATIVES; EXTRACT
• ISSN: 1747-0277; 1747-0285
• DOI: 10.1111/j.1747-0285.2011.01194.x

Here, we describe the practical synthesis and biological properties of bergenin and its structural analogs. Synthetic bergenin compounds were prepared by acylation of bergenin. These compounds were then evaluated for suppression of lipopolysaccharide‐induced nitric oxide (NO) generation in cultured cells and anti‐narcotic effects on morphine‐dependent mice. We found that bergenin derivatives showed potent anti‐inflammatory activity (suppression of NO generation) at concentrations ranging from 20 to 30 μmin vitro, and bergenin derivatives (10–20 mg/kg) exhibited significant anti‐narcotic effects on morphine dependence in mice. These results suggest the potential utility of bergenin and its analogs as anti‐narcotic agents and the design of more potent anti‐inflammatory compounds. We have demonstrated simple and practical synthesis and evaluation of bergenin derivatives. It was found that the bergenin derivatives showed potent anti‐inflammatory (suppressor of NO generation) with the concentration range 20–30 μmin vitro, and bergenin derivatives (10–20 mg/kg) exhibited significant anti‐narcotic effect on morphine dependence in mice.