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Phytochemistry ; 171: 112247, 2020 Mar.
Article in English | MEDLINE | ID: mdl-31927201

ABSTRACT

Four previously undescribed acylated iridoid glucosides, linaburiosides A‒D, one undescribed iridoid, 7-deoxyiridolactonic acid, and one known acylated iridoid glucoside, iridolinarin C, were isolated from the aerial parts of a Mongolian traditional herbal medicine, Linaria buriatica. Linaburiosides A‒D had an acyl moiety corresponding to 7-deoxyiridolactonic acid. Detailed spectroscopic analyses of linaburiosides A‒D and 7-deoxyiridolactonic acid led to the assignment of their structures. The absolute configuration of 7-deoxyiridolactonic acid was elucidated by application of the PGME method; those of linaburiosides A‒D were assigned on the basis of chemical conversions, as well as application of the modified Mosher's method. The absolute configuration of iridolinarin C was also elucidated in this study. Anti-inflammatory and antiproliferative activities of isolated compounds and their derivatives were evaluated.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Glucosides/pharmacology , Iridoids/pharmacology , Linaria/chemistry , Phytochemicals/pharmacology , A549 Cells , Acylation , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Glucosides/chemistry , Glucosides/isolation & purification , Humans , Interleukin-1beta/antagonists & inhibitors , Interleukin-1beta/biosynthesis , Iridoids/chemistry , Iridoids/isolation & purification , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , MCF-7 Cells , Microglia/drug effects , Microglia/metabolism , Molecular Conformation , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Tumor Cells, Cultured
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