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Bioorg Med Chem Lett. 2009 Feb 1;19(3):882-6. doi: 10.1016/j.bmcl.2008.11.100. Epub 2008 Dec 3.

Novel NGF-potentiating diterpenoids from a Brazilian medicinal plant, Ptychopetalum olacoides.

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Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Yamashiro-cho, Tokushima 770-8514, Japan.


From the MeOH extract of Ptychopetalum olacoides, which is used in Brazilian folk medicine for the treatment of chronic degenerative conditions of the nervous system, four novel clerodane-type diterpenoids named 6alpha,7alpha-dihydroxyannonene (1), 7alpha,20-dihydroxyannonene (2), 7alpha-hydroxysolidagolactone I (3), and ptycho-6alpha,7alpha-diol (4) were isolated by bioassay-directed fractionation using NGF-differentiated PC12 cells. The structures of 1-4 were established by extensive NMR spectroscopic analyses and chemical conversion. Compounds 1 and 2 significantly enhanced NGF-mediated neurite outgrowth in PC12 cells at concentrations ranging from 0.1 to 50.0 microM for 1 and 0.1 to 30.0 microM for 2, whereas 3 and 4 had no morphological effect on NGF-mediated PC12 cells in the same concentration range. The structure-activity relationship of these compounds is also discussed.

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