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Journal of Ocean University of China

, Volume 17, Issue 4, pp 967–972 | Cite as

Synthesis and Neuroprotective Activity of Neolamellarin A Analogues

  • Meng Zhang
  • Ruijuan Yin
  • Yiran Zhang
  • Cui Hao
  • Lijuan Zhang
  • Tao Jiang
Article
  • 10 Downloads

Abstract

Alkaloids are a class of natural products with a wide range of biological activities. Due to the special living environment, the alkaloids from marine sponges have exhibited different biological activities and promising medical application potential. Neolamellarin A is a marine alkaloid possessing bisaryl-pyrrole structural features. Here, the synthesis of 12 different 3,4-bisaryl-N-alkylated permethylated analogues of neolamellarin A and their outstanding neuroprotective activity in PC12 cells are presented and discussed.

Key words

alkaloids neolamellarin A synthesis PC12 cells neuroprotective activity 

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Notes

Acknowledgements

This study is supported by the National Natural Science Foundation of China (Nos. 21171154 and 81672585), the Key Technology Fund of Shandong Province (No. 2016ZDJS07 A07), and the Taishan Scholar Fellowship of Shandong Province in China to L. Z.

References

  1. Ayedi, M. A., Le Bigot, Y., Ammar, H., Abid, S., El Gharbi, R., and Delmas, M., 2013. ChemInform abstract: Synthesis of primary amines by one-pot reductive amination of aldehydes. ChemInform, 43 (44): 2127–2133, DOI: 10.1002/chin.201343053.Google Scholar
  2. Bailly, C., 2014. Lamellarins: A tribe of bioactive marine natural products. In: Outstanding Marine Molecules. LA Barre, S., and Kornprobst, J., eds., Wiley-VCH Verlag GmbH & Co. KGaA, 377–386.CrossRefGoogle Scholar
  3. Bharate, J. B., Singh, S., Wani, A., Sharma, S., Joshi, P., Khan, I. A., Kumar, A., Vishwakarma, R. A., and Bharate, S. B., 2015. Discovery of 4-acetyl-3-(4-fluorophenyl)-1-(p-tolyl)-5-methy-lpyrrole as a dual inhibitor of human P-glycoprotein and Staphylococcus aureus Nor A efflux pump. Organic & Biomolecular Chemistry, 19 (13): 5424–5431, DOI: 10.1039/c5ob00246j.CrossRefGoogle Scholar
  4. Fan, A. L., Lin, W. H., and Jia, Y. X., 2011. Recent progress in the research on lamellarins and related pyrrole-derived alkaloids from marine organisms. Journal of Chinese Pharmaceutical Sciences, 5 (20): M5, DOI: 10.5246/jcps.2011.05.054.Google Scholar
  5. Fan, H., Peng, J., Hamann, M. T., and Hu, J., 2008. ChemInform abstract: Lamellarins and related pyrrole-derived alkaloids from marine organisms. ChemInform, 18 (39): 264–287, DOI: 10.1002/chin.200818251.Google Scholar
  6. Hao, C., Gao, L., Zhang, Y., Wang, W., Yu, G., Guan, H., Zhang, L., and Li, C., 2015. Acetylated chitosan oligosaccharides act as antagonists against glutamate-induced PC12 cell death via Bcl-2/Bax signal pathway. Marine Drugs, 3 (13): 1267–1289, DOI: 10.3390/md13031267.CrossRefGoogle Scholar
  7. He, Y., Lan, Y., Liu, Y., Yu, H., Han, Z., Li, X., and Zhang, L., 2016. Pingyangmycin and bleomycin share the same cytotoxicity pathway. Molecules, 7 (21): DOI: 10.3390/molecules 21070862.Google Scholar
  8. Li, Q., Fan, A., Lu, Z., Cui, Y., Lin, W., and Jia, Y., 2010. One-pot AgOAc-mediated synthesis of polysubstituted pyrroles from primary amines and aldehydes: Application to the total synthesis of purpurone. Organic Letters, 18 (12): 4066–4069, DOI: 10.1021/ol101644g.CrossRefGoogle Scholar
  9. Liu, R., Liu, Y., Zhou, Y. D., and Nagle, D. G., 2007. Molecular targeted antitumor agents. 15. Neolamellarins from the marine sponge Dendrilla nigra inhibit hypoxia-inducible factor-1 activation and secreted vascular endothelial growth factor production in breast tumor cells. Journal of Natural Products, 11 (70): 1741–1745, DOI: 10.1021/np070206e.CrossRefGoogle Scholar
  10. Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65 (1-2): 55–63, DOI: 10.1016/0022-1759(83)90303-4.CrossRefGoogle Scholar
  11. Plisson, F., Huang, X. C., Zhang, H., Khalil, Z., and Capon, R. J., 2012. Lamellarins as inhibitors of P-glycoprotein-mediated multidrug resistance in a human colon cancer cell line. Chemistry Asian Journal, 7 (7): 1616–1623, DOI: 10.1002/asia.201101049.CrossRefGoogle Scholar
  12. Quesada, A. R., Grávalos, M. G., and Puentes, J. F., 1996. Polyaromatic alkaloids from marine invertebrates as cytotoxic compounds and inhibitors of multidrug resistance caused by P-glycoprotein. British Journal of Cancer, 74 (5): 677–682, DOI: 10.1038/bjc.1996.421.CrossRefGoogle Scholar
  13. Rosowsky, A., Chen, H., Fu, H., and Queener, S. F., 2003. Synthesis of new 2,4-Diaminopyrido[2,3-d]pyrimidine and 2,4-Diaminopyrrolo[2,3-d]pyrimidine inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductase. Bioorganic & Medicinal Chemistry, 1 (11): 59–67, DOI: 10.1016/S0968-0896(02)00325-5.CrossRefGoogle Scholar
  14. Tong, S., Zhang, M., Wang, S., Yin, R., Yu, R., Wan, S., Jiang, T., and Zhang, L., 2016. Isothiouronium modification empowers pyrimidine-substituted curcumin analogs potent cytotoxicity and Golgi localization. European Journal of Medicinal Chemistry, (123): 849–857, DOI: 10.1016/j.ejmech.2016.07.071.CrossRefGoogle Scholar
  15. Yin, R., Jiang, L., Wan, S., and Jiang, T., 2015. Efficient syntheses of permethylated derivatives of neolamellarin A, a pyrrolic marine natural product. Journal of Ocean University of China, 2 (14): 329–334, DOI: 10.1007/s11802-015-2372-z.CrossRefGoogle Scholar
  16. Yin, R., Zhang, M., Hao, C., Wang, W., Qiu, P., Wan, S., Zhang, L., and Jiang, T., 2013. Different cytotoxicities and cellular localizations of novel quindoline derivatives with or without boronic acid modifications in cancer cells. Chemical Communications (Camb), 76 (49): 8516–8518, DOI: 10.1039/c3cc 45203d.CrossRefGoogle Scholar
  17. Zhang, P. Y., Wong, I. L., Yan, C. S., Zhang, X. Y., Jiang, T., Chow, L. M., and Wan, S. B., 2010. Design and syntheses of permethyl ningalin B analogues: Potent multidrug resistance (MDR) reversal agents of cancer cells. Journal of Medicinal Chemistry, 14 (53): 5108–5120, DOI: 10.1021/jm100035c.CrossRefGoogle Scholar

Copyright information

© Science Press, Ocean University of China and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Systems Biology and Medicine Center for Complex DiseasesAffiliated Hospital of Qingdao UniversityQingdaoChina
  2. 2.School of Medicine and PharmacyOcean University of ChinaQingdaoChina
  3. 3.Marine Biomedical Research Institute of QingdaoQingdaoChina

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