N-galloylhydroxylamine from pentagalloylglucose: analgesic and anti-inflammatory activities, semi-synthesis

ABSTRACT

The pericarp of Harpullia pendula, 1, 2, 3, 4, 6-penta-O-galloyl-beta-D-glucopyranose, as a major gallotannin [7], was isolated together with other six polyphenolic metabolites. Their structures were established as gallic acid [1], methylgallate [2], ethylgallate [3], chlorogenic acid [4], 1, 2, 6-tri-O-galloyl-beta-D-glucopyranose [5] 1, 2, 4, 6-teta-O-galloyl-beta-Dglucopyranose [6], according the chromatographic properties, chemical and spectroscopic analyses. Compound 7 was subjected to a semi-synthesis with hydroxylamine hydrochloride resulting in a significant analgesic and anti-inflammatory N-galloyl-hydroxylamine bioactive product [8], which exhibited at dose [100 mg/kg] high significant analgesic and anti-inflammatory activities compared with indomethacin in dose [10 mg/kg]