Carpesium divaricatum Sieb. & Zucc. Revisited: Newly Identified Constituents from Aerial Parts of the Plant and Their Possible Contribution to the Biological Activity of the Plant

• Published in: Molecules (Basel, Switzerland) Switzerland), 2019-04, Vol.24 (8), p.1614
• Main Authors: Kłeczek, Natalia, Michalak, Barbara, Malarz, Janusz, Kiss, Anna Karolina, Stojakowska, Anna
• Format: Article
• Language: English
• Subjects: 12-oxo-phytodienoic acid; Acids; anti-inflammatory; Asteraceae - chemistry; Biological activity; Caffeic acid; caffeic acid derivatives; Caffeic Acids - chemistry; Caffeic Acids - isolation & purification; Caffeic Acids - pharmacology; Carpesium divaricatum; Chemokine CCL2 - genetics; Chemokines; Chlorogenic acid; Chlorogenic Acid - chemistry; Chlorogenic Acid - isolation & purification; Chromatography; Chromatography, High Pressure Liquid; Constituents; Cytokines; Cytotoxicity; Fatty Acids, Unsaturated - chemistry; Fatty Acids, Unsaturated - isolation & purification; Fatty Acids, Unsaturated - pharmacology; Fractionation; Functional foods & nutraceuticals; Gene Expression Regulation - drug effects; High-performance liquid chromatography; Humans; IL-1β; Interleukin 8; Interleukin-8 - genetics; Leukocytes (neutrophilic); Lipophilic; Lipopolysaccharides; Lipopolysaccharides - pharmacology; Liquid chromatography; Metabolites; Monocyte chemoattractant protein 1; Neutrophils; Neutrophils - drug effects; Plant Components, Aerial - chemistry; Plant Shoots - chemistry; Reactive oxygen species; Reactive Oxygen Species - chemistry; ROS; Seeds; Shoots; Tumor Necrosis Factor-alpha - genetics; Tumor necrosis factor-α
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24081614

Sieb. & Zucc. has a long history of use as both a medicinal and a food plant. However, except for terpenoids, its chemical constituents have remained poorly investigated. The composition of hydroalcoholic extract from aerial parts of was analyzed by HPLC-DAD-MS , revealing the presence of numerous caffeic acid derivatives that were formerly unknown constituents of the plant. In all, 17 compounds, including commonly found chlorogenic acids and rarely occurring butyryl and methylbutyryl tricaffeoylhexaric acids, were tentatively identified. Fractionation of lipophilic extract from cultivated shoots led to the isolation of 12-oxo-phytodienoic acid (12-OPDA), which is a newly identified constituent of the plant. The compound, at concentrations of 0.5, 1.0, and 2.5 μM, significantly reduced IL-8, IL-1β, TNFα, and CCL2 excretion by lipopolysaccharide (LPS)-stimulated human neutrophils. Reactive oxygen species (ROS) production induced by f-MLP was also significantly diminished in the neutrophils pretreated by 12-OPDA. The newly identified constituents of the plant seem to be partly responsible for its pharmacological activity and elevate the value of as a potential functional food.