Abstract
One new guaiane-type sesquiterpene glycoside, 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (1), was isolated from the whole herb of Ainsliaea fragrans (Compositae), together with five known sesquiterpene lactones: 8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (2), 8alpha-hydroxy-11alpha,13-dihydrozaluzanin C (3), 3alpha-hydroxy-11beta,13-dihydro-8alpha-O-beta-D-glucozaluzanin C (4), 3beta-hydroxy-11beta,13-dihydro-8alpha-O-beta-D-glucozaluzanin C (5), 3beta-O-beta-D-glucozaluzanin C (6). The structures of isolated compounds were established by means of 1D and 2D NMR spectroscopy and chemical methods. All isolates obtained in the present study were evaluated for their inhibitory effects against cyclooxygenases-1 and 2 in vitro, and the structure-activity relationships were also discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Asteraceae / chemistry*
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Chromatography, High Pressure Liquid
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Cyclooxygenase 1 / metabolism*
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Cyclooxygenase 2 Inhibitors / isolation & purification*
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Cyclooxygenase 2 Inhibitors / pharmacology*
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Cyclooxygenase Inhibitors / isolation & purification*
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Cyclooxygenase Inhibitors / pharmacology*
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Glucosides / isolation & purification*
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Glucosides / pharmacology*
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Hydrolysis
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Molecular Conformation
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Sesquiterpenes / chemistry*
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Sesquiterpenes / isolation & purification
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Sesquiterpenes / pharmacology*
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Sesquiterpenes, Guaiane / isolation & purification*
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Sesquiterpenes, Guaiane / pharmacology*
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Spectrometry, Mass, Electrospray Ionization
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Spectrophotometry, Ultraviolet
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Spectroscopy, Fourier Transform Infrared
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Structure-Activity Relationship
Substances
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2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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Glucosides
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Sesquiterpenes
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Sesquiterpenes, Guaiane
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Cyclooxygenase 1