title: Isolation and biological activity of a novel cadinane-type sesquiterpenoid from the essential oil of Alangium salviifolium.
abstract: The components of the essential oil from the roots of Alangium salviifolium were analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Ninety compounds, representing 74.5% of the total oil, were identified; the main components of the oil were epi-α-cadinol, followed by trans-2-hydroxycalamenene, cadalene, and cadina-4,10(15)-dien-3-one. A further unknown component comprised 5.5% of the oil. Therefore, the essential oil was purified by flash column chromatography to isolate this component. Its structure was established using extensive spectroscopic data analyses, including NMR, HR-EI-MS, and IR. The results showed that this isolated compound was (-)-7, 8-dihydroxycalamenal, which is a novel cadinane-type sesquiterpenoid. This compound was tested for its antioxidant activity and inhibition of tyrosinase, and showed particularly strong inhibition effects.
authors.affiliation: Picaso Cosmetics Laboratory Limited.
authors.forename: Nobuo
authors.initials: N
authors.lastname: Yagi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nakahashi
authors.forename: Yusei
authors.initials: Y
authors.lastname: Kashima
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D032604:Alangiaceae / Q000737:chemistry*; D000975:Antioxidants; D002845:Chromatography / Q000379:methods; D004791:Enzyme Inhibitors; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D009822:Oils, Volatile / Q000737:chemistry* / Q000302:isolation & purification; D010938:Plant Oils / Q000737:chemistry* / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013764:Tetrahydronaphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: C000598335:7,8-dihydroxycalamenal; D000975:Antioxidants; D004791:Enzyme Inhibitors; D009822:Oils, Volatile; D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013764:Tetrahydronaphthalenes; C508039:cadinane; D014442:Monophenol Monooxygenase