New norlignan enantiomers from the fruit of Crataegus pinnatifida with neuroprotective activities |
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| Institution: | 1. Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China;2. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;3. Chinese People’s Liberation Army Logistics Support Force No. 967 Hospital, Dalian 116021, China;1. Department of Natural Product Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Ji’nan 250012, China;2. Department of Thoracic Surgery, Qilu Hospital of Shandong University, Ji’nan 250012, China;1. State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau 999078, China;2. State Key Laboratory of Drug Research, & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;3. School of Life Science and Technology, Shanghai Tech University, Shanghai 201203, China;4. School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China;1. Department of Natural Products Chemistry, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People''s Republic of China;2. Xiamen Institute for Food and Drug Quality Control, Xiamen 3161012, People''s Republic of China;3. Chinese People''s Liberation Army 210 Hospital, Dalian 116021, People''s Republic of China;1. School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery (Ministry of Education), Shenyang Pharmaceutical University, Shenyang 110016, People''s Republic of China;2. Chinese People''s Liberation Army 210 Hospital, Dalian 116021, People''s Republic of China;1. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China;2. Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China;3. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China;4. College of Pharmaceutical and Biological Engineering, Shenyang University of Chemical Technology, Shenyang 110142, People’s Republic of China |
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| Abstract: | (±)-Crataegusnorin A (1a/1b) and B (2a/2b), two pairs of rare 8,9′-epoxy-type norlignan enantiomers featuring a γ-butyrolactone ring, were isolated from the fruit of Crataegus pinnatifida. Their structures were determined via extensive spectroscopic analyses. Gauge-independent atomic orbital (GIAO) NMR chemical shift calculations, combined with the advanced statistical method DP4+ were employed to establish the relative configurations of four compounds. Next, chiral separation was accomplished by chiral chromatographic column and the absolute configurations of the four compounds were unambiguously assigned by comparison between their experimental electronic circular dichroism curves with the quantum-mechanically calculated curves based on time-dependent density functional theory (TDDFT). All the isolates were evaluated for their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y cells. The results showed that two pairs of enantiomers 1a/1b and 2a/2b displayed diff ;erent effect on neuroprotective activity. Among them, compound 2a displayed the most potent neuroprotective effect. Further flow cytometry analysis indicated that 2a could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis. |
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| Keywords: | Norlignan enantiomer Neuroprotective activity SH-SY5Y cells Apoptosis |
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