Fragilides K and L, New Briaranes from the Gorgonian Coral Junceella fragilis

• Published in: Molecules (Basel, Switzerland) Switzerland), 2018-06, Vol.23 (7), p.1510
• Main Authors: Zheng, Li-Guo, Chang, Yu-Chia, Hu, Chiung-Chih, Wen, Zhi-Hong, Wu, Yang-Chang, Sung, Ping-Jyun
• Format: Article
• Language: English
• Subjects: Animals; Anthozoa - chemistry; Anthozoa - metabolism; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; briarane; Carbohydrate Conformation; Cell Survival - drug effects; Communication; COX-2; Cyclohexane; Cyclooxygenase 2 - genetics; Cyclooxygenase 2 - metabolism; Cyclooxygenase-2; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; fragilide; Gene Expression - drug effects; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; Heterocyclic Compounds, 4 or More Rings - pharmacology; Inflammation; iNOS; Junceella fragilis; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; Lipopolysaccharides; Lipopolysaccharides - antagonists & inhibitors; Lipopolysaccharides - pharmacology; Macrophages; Metabolites; Mice; Nitric oxide; Nitric Oxide Synthase Type II - antagonists & inhibitors; Nitric Oxide Synthase Type II - genetics; Nitric Oxide Synthase Type II - metabolism; Nitric-oxide synthase; Plant Proteins - chemistry; Plant Proteins - isolation & purification; Plant Proteins - pharmacology; Proteins; RAW 264.7 Cells
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23071510

Two new briarane metabolites—fragilides K ( ) and L ( )—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V ( ⁻ )—were extracted and purified from , a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes and were determined and the cyclohexane rings in and were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes , , and inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes and suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.