Four new compounds from the bulbs of Lycoris aurea with neuroprotective effects against CoCl2 and H2O2-induced SH-SY5Y cell injuries

다국어 초록 (Multilingual Abstract)

Three new alkaloids, 2a-hydroxy-6-O-n-butyloduline,O-n-butyllycorenine, (-)-N-(chloromethyl)lycoramine(1–3), and a new phenolic compound, ((7S)-7-(4-hydroxyphenyl)-7-hydroxypropyl)-20-methylbenzene-30,60-diol (14), along with ten known alkaloids (4–13), wereisolated from the bulbs of Lycoris aurea collected fromHuaihua County of Hunan Province, China. Their structureswere elucidated by spectroscopic methods includingHRESIMS, UV, IR, and NMR. All the isolated compoundswere tested for their neuroprotective effects against CoCl2and H2O2-induced SH-SY5Y cell death. Compounds 1–7and 10 exhibited significant neuroprotective effects againstCoCl2-induced SH-SY5Y cell injury, while compounds1–5, 7, 10 and 12 showed obvious neuroprotective effectsagainst H2O2-induced SH-SY5Y cell death.

참고문헌 (Reference)

1 Chandra, J., "Triggering and modulation of apoptosis by oxidative stress" 29 : 323-333, 2000

2 Tsuda, Y., "Total synthesis of the Amaryllidaceae alkaloids, lycorine and zephyranthine. Journal of the Chemical Society" 1972–1999 : 1358-1363, 1979

3 Bohno, M., "Total synthesis of Amaryllidaceae alkaloids, (?)-vittatine and(?)-haemanthamine, starting from D-glucose" 63 : 6977-6989, 2007

4 Li, H., "Studies on the alkaloids of Amaryllidaceae. Part X. Alkaloids of Lycoris guangxiensis" 53 : 259-261, 1987

5 Jeffs, P. W., "Structures of 9-O-demethylhomolycorine and 5a-hydroxyhomolycorine. Alkaloids of Crinum defixum, C. scabrum, and C. latifolium. Assignment of aromatic substitution patterns from 1H-coupled 13C Spectra" 50 : 1732-1737, 1985

6 Kreh, M., "O-Methyloduline and N-demethylmasonine, alkaloids from Narcissus pseudonarcissus" 38 : 1533-1535, 1995

7 Kim, S., "Neuroprotective effects of 3, 5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells" 19 : 243-245, 2005

8 Kihara, M., "Isolation and structure elucidation of a novel alkaloid, incartine, a supposed biosynthetic intermediate, from flowers of Lycoris incarnata" 42 : 289-292, 1994

9 Harken, R. D., "Interconversions in the pluviine–lycorenine series" 41 : 2450-2454, 1976

10 Cuong, T. D., "Inhibitory effect on NO production of phenolic compounds from Myristica fragrans" 21 : 6884-6887, 2011

11 Matusch, R., "Formation, x-ray crystal structure, and absolute configuration of(-)-N-(chloromethyl)galanthaminium chloride" 77 : 1611-1615, 1994

12 Zeno, S., "CoCl2 induces apoptosis via the 18 kDa translocator protein in U118MG human glioblastoma cells" 48 : 4652-4661, 2009

13 Lee, J., "CoCl2 induces apoptosis through the mitochondria-and death receptor-mediated pathway in the mouse embryonic stem cells" 379 : 133-140, 2013

14 Kornienko, A., "Chemistry, biology, and medicinal potential of narciclasine and its congeners" 108 : 1982-2014, 2008

15 Jin, Z., "Amaryllidaceae and Sceletium alkaloids" 26 : 363-381, 2009

16 Jin, Z., "Amaryllidaceae and Sceletium alkaloids" 24 : 886-905, 2007

17 Jin, Z., "Amaryllidaceae and Sceletium alkaloids" 28 : 1126-1142, 2011

18 Yang, Y., "Alkaloids from the bulbs of Lycoris aurea" 88 : 2550-2553, 2005

19 Almanza, G. R., "Alkaloids from Narcissus cv. Salome" 43 : 1375-1378, 1996

20 Kihara, M., "Alkaloidal constituents of the flowers of Lycoris radiata Herb. (Amaryllidaceae)" 39 : 1849-1853, 1991

21 Lo´pez, S., "Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts" 71 : 2521-2529, 2002

22 Pi, H. F., "A new alkaloid from Lycoris aurea" 20 : 1319-1320, 2009