Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)

• Published in: Chemical & Pharmaceutical Bulletin Vol. 56; no. 1; pp. 60 - 63
• Main Authors: Kuroyanagi, Masanori, Ikeda, Ryuya, Gao, Hui Yuan, Muto, Norio, Otaki, Keisuke, Sano, Toshikazu, Kawahara, Nobuo, Nakane, Takahisa
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 01.01.2008; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemistry; 4-Butyrolactone - isolation & purification; 4-Butyrolactone - pharmacology; Animals; Benzodioxoles; Chamaecyparis - chemistry; Chamaecyparis obtusa; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Cupressus; Dioxoles - chemistry; Dioxoles - isolation & purification; Dioxoles - pharmacology; Life Sciences & Biomedicine; lignan; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; Molecular Structure; Nerve Growth Factor - chemistry; Nerve Growth Factor - isolation & purification; Nerve Growth Factor - pharmacology; neurite outgrowth-promoting activity; Neurites - drug effects; PC12 cell; PC12 Cells; Pharmacology & Pharmacy; Physical Sciences; Plant Leaves - chemistry; Plants, Medicinal - chemistry; Rats; Science & Technology; sesquiterpene–lignan conjugate; Chamaecyparis obtusa; lignan; NMR; JAPONICA; EPIDERMAL-CELLS; PC12 cell; neurite outgrowth-promoting activity; FORMOSANA; H-1; sesquiterpene - lignan conjugate; FUROFURAN LIGNANS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.56.60

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.