Anti-inflammatory ent-kaurenoic acids and their glycosides from Gochnatia decora

• Published in: Phytochemistry (Oxford) 2017-05, Vol.137, p.174-181
• Main Authors: Zhang, Mi, Zhao, Chenxing, Dai, Weifeng, He, Jing, Jiao, Shiyun, Li, Baocai
• Format: Article
• Language: English
• Subjects: Animals; Anti-inflammatory; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Asteraceae - chemistry; China; Compositae; Diterpenes - isolation & purification; Diterpenes - pharmacokinetics; ent-kaurane; Glycosides - isolation & purification; Glycosides - pharmacology; Gochnatia decora; Leukocyte Elastase - antagonists & inhibitors; Male; Mice; Molecular Structure; Neutrophil elastase inhibition; Nitric Oxide - metabolism; Plant Bark - chemistry; Plant Extracts - pharmacology; Plants, Medicinal - chemistry; RAW 264.7 Cells
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2017.02.021

Nineteen ent-kaurane diterpenes were isolated and identified from the barks of Gochnatia decora (Kurz) A. L. Cabrera (Compositae), which has been used as an ethnic medicine for treating cough, asthma and wounds in southwestern China. Among them, six compounds are previously undescribed ent-kaurenoic acids, and a known compound, 7β,15β-dihydroxy-ent-kaur-16-en-19-oic acid, was obtained for the first time from nature. Based on its traditional effects in Chinese folk, the potential anti-inflammatory activities of its methanol extracts (ME) and isolated diterpenes were evaluated by the tests of the xylene-induced ear swelling in mice, lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage cellular RAW 264.7 and inhibition assay of neutrophil elastase, respectively, resulting that ME performed obvious effect against mouse ear swelling with a dose-dependent inhibition in vivo, and nine compounds showed significant inhibition of NO production in vitro, with IC50 values ranging from 0.042 to 8.22 μM, while they also exhibited inhibition of neutrophil elastase at 100 μM in vitro, speculating that those diterpenes may be the active substances correlated with their traditional efficacy. [Display omitted] •Six ent-kauranes and thirteen known analogs were isolated from the barks of Gochnatia decora.•Nine compounds showed significant inhibition of NO production in vitro.•Ten compounds exhibited obvious inhibition of neutrophil elastase in vitro.