Phenolic compounds from the aerial parts of Clematis viticella L. and their in vitro anti-inflammatory activities

• Published in: Natural product research 2019-09, Vol.33 (17), p.2541-2544
• Main Authors: Kırmızıbekmez, Hasan, İnan, Yiğit, Reis, Rengin, Sipahi, Hande, Gören, Ahmet C., Yeşilada, Erdem
• Format: Article
• Language: English
• Subjects: Animals; anti-inflammatory activity; Anti-inflammatory agents; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Caffeic acid; Clematis - chemistry; Clematis viticella; Coumaric acid; flavonoid glycosides; Flavonoids; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - pharmacology; Glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Humans; hydroxytyrosol; Indomethacin; Inflammation; L-Rhamnopyranoside; Lipopolysaccharides; Macrophages; Macrophages - metabolism; Mice; Molecular Structure; Neopterin; Nitric Acid - metabolism; NMR; Nuclear magnetic resonance; p-Coumaric acid; p-Hydroxybenzoic acid; Phenolic acids; Phenols; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Plant Components, Aerial - chemistry; Plant Extracts - chemistry; Quercetin; RAW 264.7 Cells; Spectrum Analysis; Tumor Necrosis Factor-alpha - drug effects; Tumor Necrosis Factor-alpha - metabolism; Tumor necrosis factor-α
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2018.1448815

Phytochemical investigations on the EtOH extract of Clematis viticella led to the isolation of six flavonoid glycosides, isoorientin (1), isoorientin 3′-O-methyl ether (2), quercetin 7-O-α-L-rhamnopyranoside (3), quercetin 3,7-di-O-α-L-rhamnopyranoside (4), manghaslin (5) and chrysoeriol 7-O-β-D-glucopyranoside (6), one phenylethanol derivative, hydroxytyrosol (7), along with three phenolic acids, caffeic acid (8), (E)-p-coumaric acid (9) and p-hydroxybenzoic acid (10). The structures of the isolates were elucidated on the basis of NMR and HR-MS data. All compounds were isolated from C. viticella for the first time. Compounds 7 and 8 showed significant anti-inflammatory activity at 100 μM by reducing the release of NO in LPS-stimulated macrophages comparable to positive control indomethacin. Compounds 3 and 7 exhibited anti-inflammatory activity through lowering the levels of TNF-α while 1, 3 and 5 decreased the levels of neopterin better than the positive controls.