Bioactive butylphthalide derivatives from Ligusticum chuanxiong |
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| Institution: | 1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100050, China;2. Institute for Control of Chinese Traditional Medicine and Ethnic Medicine, National Institutes for Food and Drug Control, Beijing 100050, China;1. State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People''s Republic of China;2. Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, Medical University of South Carolina, Charleston, SC 29425, United States;3. Department of BioMolecular Sciences, Division of Medicinal Chemistry, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, MS 38677-1848, United States;4. Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, United States;5. Department of Biochemistry and Molecular Biology, Medical University of South Carolina, Charleston, SC 29425, United States;6. Department of BioMolecular Sciences, Division of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, MS 38677-1848, United States |
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| Abstract: | Seven new butylphthalide derivatives, ligusticumolide A-G (1–7), together with two known butylphthalide derivatives (8–9) were isolated from an ethanol extract of Ligusticum chuanxiong Hort. The structures of these derivatives were elucidated from analysis of 1D/2D NMR, UV, IR and HRESIMS data. The absolute configurations of these derivatives were determined by electronic circular dichroism (ECD) calculations and Mosher′s method. Ligusticumolide A (1) and ligusticumolide B (2) are enantiomers that were obtained by chiral separation. Ligusticumolide C (3) and ligusticumolide D (4) are diastereomers. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 4, 5, and 7–9 showed more significant hepatoprotective activity than that of the positive control drug (bicyclol) at a concentration of 10 μM (p < 0.01). |
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| Keywords: | Butylphthalide derivatives Structure elucidation Hepatoprotective activity |
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