Neurite outgrowth-promoting active constituents of the Japanese cypress (Chamaecyparis obtusa).
In the screening of biologically active constituents from woody plants, the methanol extract of leaves of Chamaecyparis obtusa showed potent neurite outgrowth-promoting activity in neuronal PC12 cells. The ethyl acetate-soluble fraction of the methanol extract showed potent activity and was separated by means of various chromatographic methods to give the two new compounds 1 and 2, as well as 11 known lignan and sesquiterpene derivatives. The structures of the new compounds were determined to be 9-O-acetyldihydrosesamin (1) and 9-O-(11-hydroxyeudesman-4-yl)dihydrosesamin (2), respectively, in NMR studies including 2D-NMR experiments. Of the 13 compounds, the known compound hinokinin (5) and the new compound 2 showed potent neurite outgrowth-promoting activity in PC 12 cells.
Kuroyanagi
Masanori
M
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, Hiroshima, Japan. kuroyang@pu-hiroshim.ac.jp
Ikeda
Ryuya
R
Gao
Hui Yuan
HY
Muto
Norio
N
Otaki
Keisuke
K
Sano
Toshikazu
T
Kawahara
Nobuo
N
Nakane
Takahisa
T
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D052117:Benzodioxoles; D029780:Chamaecyparis / Q000737:chemistry*; D004149:Dioxoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D020932:Nerve Growth Factor / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016501:Neurites / Q000187:drug effects*; D016716:PC12 Cells; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats
C525686:9-O-(11-hydroxyeudesman-4-yl)dihydrosesamin; C525685:9-O-acetyldihydrosesamin; D052117:Benzodioxoles; D004149:Dioxoles; D017705:Lignans; C475934:hinokinin; D020932:Nerve Growth Factor; D015107:4-Butyrolactone