title: Novel NGF-potentiating diterpenoids from a Brazilian medicinal plant, Ptychopetalum olacoides.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Wanxia
authors.initials: W
authors.lastname: Tang
authors.forename: Miwa
authors.initials: M
authors.lastname: Kubo
authors.forename: Kenichi
authors.initials: K
authors.lastname: Harada
authors.forename: Hideaki
authors.initials: H
authors.lastname: Hioki
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
mesh_terms: D000818:Animals; D001681:Biological Assay; D002454:Cell Differentiation; D004224:Diterpenes / Q000737:chemistry*; D045785:Diterpenes, Clerodane / Q000737:chemistry; D004357:Drug Synergism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D020932:Nerve Growth Factor / Q000378:metabolism*; D016501:Neurites / Q000378:metabolism; D031656:Olacaceae / Q000378:metabolism*; D016716:PC12 Cells; D010946:Plants, Medicinal / Q000737:chemistry / Q000378:metabolism*; D051381:Rats; D013055:Spectrophotometry, Infrared / Q000379:methods
chemical_list: D004224:Diterpenes; D045785:Diterpenes, Clerodane; D020932:Nerve Growth Factor