Anti-inflammatory effects of 7-methoxycryptopleurine and structure–activity relations of phenanthroindolizidines and phenanthroquinolizidines

A cryptopleurine analogue, 7-methoxycryptopleurine, a phenanthroquinolizidine, was first found to exert potent anti-inflammatory activity in vitro and in vivo as well as have remarkable cytotoxic activity against cancer cells. The non-planar structure between the two major moieties, phenanthrene and...

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Veröffentlicht in:Biochemical and biophysical research communications 2007-03, Vol.354 (4), p.942-948
Hauptverfasser: Yang, Cheng-Wei, Chuang, Ta-Hsien, Wu, Pei-Lin, Huang, Wen-Hsin, Lee, Shiow-Ju
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Sprache:eng
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Zusammenfassung:A cryptopleurine analogue, 7-methoxycryptopleurine, a phenanthroquinolizidine, was first found to exert potent anti-inflammatory activity in vitro and in vivo as well as have remarkable cytotoxic activity against cancer cells. The non-planar structure between the two major moieties, phenanthrene and indolizidine/quinolizidine, played a crucial role in the activity of phenanthroindolizidines or phenanthroquinolizidines in terms of cytotoxic effects on cancer cells and anti-inflammatory activity. We also showed that increase in planarity and rigidity of the indolizidine/quinolizidine moiety and change of the amine group into an amide by introducing a keto group to phenanthroindolizidines or phenanthroquinolizidines at the equivalent position 9 of tylophorine significantly reduced their activities. Moreover, in general, phenanthroquinolizidines are more potent than their respective phenanthroindolizines.
ISSN:0006-291X
1090-2104
DOI:10.1016/j.bbrc.2007.01.065