Abstract
Three new alkaloids, 2α-hydroxy-6-O-n-butyloduline, O-n-butyllycorenine, (−)-N-(chloromethyl)lycoramine (1–3), and a new phenolic compound, ((7S)-7-(4-hydroxyphenyl)-7-hydroxypropyl)-2′-methylbenzene-3′,6′-diol (14), along with ten known alkaloids (4–13), were isolated from the bulbs of Lycoris aurea collected from Huaihua County of Hunan Province, China. Their structures were elucidated by spectroscopic methods including HRESIMS, UV, IR, and NMR. All the isolated compounds were tested for their neuroprotective effects against CoCl2 and H2O2-induced SH-SY5Y cell death. Compounds 1–7 and 10 exhibited significant neuroprotective effects against CoCl2-induced SH-SY5Y cell injury, while compounds 1–5, 7, 10 and 12 showed obvious neuroprotective effects against H2O2-induced SH-SY5Y cell death.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Almanza, G.R., J.M. Fernandez, E.W.T. Wakori, F. Viladomat, C. Codina, and J. Bastida. 1996. Alkaloids from Narcissus cv. Salome. Phytochemistry 43: 1375–1378.
Bohno, M., K. Sugie, H. Imase, Y.B. Yusof, T. Oishi, and N. Chida. 2007. Total synthesis of Amaryllidaceae alkaloids, (+)-vittatine and (+)-haemanthamine, starting from d-glucose. Tetrahedron 63: 6977–6989.
Chandra, J., A. Samali, and S. Orrenius. 2000. Triggering and modulation of apoptosis by oxidative stress. Free Radical Biology & Medicine 29: 323–333.
Cuong, T.D., T.M. Hung, M. Na, D.T. Ha, J.C. Kim, D. Lee, S. Ryoo, J.H. Lee, J.S. Choi, and B.S. Min. 2011. Inhibitory effect on NO production of phenolic compounds from Myristica fragrans. Bioorganic & Medicinal Chemistry Letters 21: 6884–6887.
Harken, R.D., C.P. Christensen, and W.C. Wildman. 1976. Interconversions in the pluviine–lycorenine series. Journal of Organic Chemistry 41: 2450–2454.
Jeffs, P.W., A. Abou-Donia, D. Campau, and D. Staiger. 1985. Structures of 9-O-demethylhomolycorine and 5α-hydroxyhomolycorine. Alkaloids of Crinum defixum, C. scabrum, and C. latifolium. Assignment of aromatic substitution patterns from 1H-coupled 13C Spectra. Journal of Organic Chemistry 50: 1732–1737.
Jin, Z. 2007. Amaryllidaceae and Sceletium alkaloids. Natural Products Reports 24: 886–905.
Jin, Z. 2009. Amaryllidaceae and Sceletium alkaloids. Natural Products Reports 26: 363–381.
Jin, Z. 2011. Amaryllidaceae and Sceletium alkaloids. Natural Products Reports 28: 1126–1142.
Kihara, M., K. Konishi, L. Xu, and S. Kobayashi. 1991. Alkaloidal constituents of the flowers of Lycoris radiata Herb. (Amaryllidaceae). Chemical & Pharmaceutical Bulletin 39: 1849–1853.
Kihara, M., L. Xu, K. Konishi, K. Kida, Y. Nagao, S. Kobayashi, and T. Shingu. 1994. Isolation and structure elucidation of a novel alkaloid, incartine, a supposed biosynthetic intermediate, from flowers of Lycoris incarnata. Chemical & Pharmaceutical Bulletin 42: 289–292.
Kim, S., R. Park, H. Jeon, Y. Kwon, and W. Chun. 2005. Neuroprotective effects of 3,5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells. Phytotherapy research: PTR 19: 243–245.
Kornienko, A., and A. Evidente. 2008. Chemistry, biology, and medicinal potential of narciclasine and its congeners. Chemical Reviews 108: 1982–2014.
Kreh, M., and R. Matusch. 1995. O-Methyloduline and N-demethylmasonine, alkaloids from Narcissus pseudonarcissus. Phytochemistry 38: 1533–1535.
Lee, J., Choi, S., Baek, M., Kim, M., Kim, H., Kim, S., Oh, S., Park, H., Kim, W., and J. Jung. 2013. CoCl2 induces apoptosis through the mitochondria- and death receptor-mediated pathway in the mouse embryonic stem cells. Molecular and Cellular Biochemistry 379: 133–140.
Li, H., G. Ma, Y. Xu, and S. Hong. 1987. Studies on the alkaloids of Amaryllidaceae. Part X. Alkaloids of Lycoris guangxiensis. Planta Medica 53: 259–261.
López, S., J. Bastida, F. Viladomat, and C. Codina. 2002. Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sciences 71: 2521–2529.
Matusch, R., M. Kreh, and U. Mueller. 1994. Formation, x-ray crystal structure, and absolute configuration of (−)-N-(chloromethyl)galanthaminium chloride. Helvetica Chimica Acta 77: 1611–1615.
Pi, H.F., P. Zhang, H.L. Ruan, Y.H. Zhang, H.D. Sun, and J.Z. Wu. 2009. A new alkaloid from Lycoris aurea. Chinese Chemical Letters 20: 1319–1320.
Tsuda, Y., T. Sano, J. Taga, K. Isobe, J. Toda, S. Takagi, M. Yamaki, M. Murata, H. Irie, and H. Tanaka. 1979. Total synthesis of the Amaryllidaceae alkaloids, lycorine and zephyranthine. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry 1972–1999: 1358–1363.
Yang, Y., S. Huang, Y. Zhao, Q. Zhao, and H. Sun. 2005. Alkaloids from the bulbs of Lycoris aurea. Helvetica Chimica Acta 88: 2550–2553.
Zeno, S., M. Zaaroor, S. Leschiner, L. Veenman, and M. Gavish. 2009. CoCl2 induces apoptosis via the 18 kDa translocator protein in U118MG human glioblastoma cells. Biochemistry-Us 48: 4652–4661.
Acknowledgments
Financial support from the Ministry of Science and Technology of the People’s Republic of China (International Cooperative Project, Grant No. 2010DFA32430) and Natural Science Foundation of China (No. 81072547, 31270394 and 30873361) is gratefully acknowledged.
Conflict of interest
All the authors have no conflict of interest to declare.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jin, A., Li, X., Zhu, YY. et al. Four new compounds from the bulbs of Lycoris aurea with neuroprotective effects against CoCl2 and H2O2-induced SH-SY5Y cell injuries. Arch. Pharm. Res. 37, 315–323 (2014). https://doi.org/10.1007/s12272-013-0188-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-013-0188-1