ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Antioxidant activity guided fractionation of extracts of the aerial parts of the title plant and HPLC separation yielded a series of oxygenated long-chain alkylcatechols. Their structures were inferred by spectroscopic methods and chemical transformations to be the novel 4-[(2S,4R,6S)-4-(acetyloxy)tetrahydro-6-pentyl-2H-pyran-2-yl]benzene-1,2diol (1a), 4-[(2S,4R6S)-tetrahydro-4-hydroxy-6-pentyl-2H-pyran-2-yl]benzene-1,2-diol (1b), 4-[(3S,5S)-5-(acetyloxy)-3-hydroxydecyl]benzene-1,2-diol (2a), 4-[(3S,5S)3-(acetyloxy)-5-hydroxydecyl]benzene-1,2-diol (2b), (3S,13Z)-1-(3,4-dihydroxyphenyl)-3-hydroxydocos-13-en-5-one (3a), (Z)-1-(3,4-dihydroxyphenyl)docos-13-en-5-one (4), besides the known l-(3,4-dihydroxyphenyl)icosan-5-one (5). The absolute configurations of the optically active compounds which are structurally related to the [n]-gingerols (6) and -diols (7) were established by the high-field 1H-NMR application of Mosher's method. All compounds are in vitro potent antioxidants, inhibiting the Fe2+-catalysed autoxidation of linoleic acid in the same order of magnitude as the commercial antioxidant 2,6-di(tert-butyl)-4-methylphenol (BHT). The dose-dependent inhibitory effects on soybean-lipoxygenase are in the μmol range, that of the most effective compound (3a) in the nmol range, hence being significantly more potent than the Known anti-inflammatory and analgesic drugs indomethacin and nordihydroguaiaretic acid.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19970800209
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