4.4 Article

Two new morphinane alkaloids from Sinomenium acutum

Journal

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
Volume 13, Issue 6, Pages 523-528

Publisher

TAYLOR & FRANCIS LTD
DOI: 10.1080/10286020.2011.574617

Keywords

Sinomenium acutum; 1-hydroxy-10-oxo-sinomenine; 4; 5-epoxy-14-hydroxy sinomenine N-oxide

Funding

  1. Shaanxi Science and Technology Commission [2010JM2014]
  2. Shaanxi Education Commission [09JS067, 2010JK407]
  3. Baoji Technology Department [08SF01-2]

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Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC50 of 27.9M. Compound 2 was tested for neuroprotective effect and showed significant activity against -amyloid25-35-induced oxidative injury (*P0.05) at 10M in PC-12 cells.

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