Tedanol: A potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis

• Published in: Bioorganic & medicinal chemistry 2009-11, Vol.17 (21), p.7542-7547
• Main Authors: Costantino, Valeria, Fattorusso, Ernesto, Mangoni, Alfonso, Perinu, Cristina, Cirino, Giuseppe, De Gruttola, Luana, Roviezzo, Fiorentina
• Format: Article
• Language: English
• Subjects: Animals; Anti-inflammatory activity; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Biological and medical sciences; COX-2 inhibitors; Cyclooxygenase 2 - chemistry; Cyclooxygenase 2 - metabolism; Cyclooxygenase 2 Inhibitors - chemistry; Cyclooxygenase 2 Inhibitors - isolation & purification; Cyclooxygenase 2 Inhibitors - pharmacology; Diterpenes; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Diterpenes, Abietane - chemistry; Diterpenes, Abietane - isolation & purification; Diterpenes, Abietane - pharmacology; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - pharmacology; General pharmacology; Magnetic Resonance Spectroscopy; Marine sponges; Medical sciences; Mice; Molecular Conformation; Nitric Oxide Synthase Type II - antagonists & inhibitors; Nitric Oxide Synthase Type II - metabolism; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Pimarane; Porifera - chemistry; Tedania ignis
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2009.09.010

Tedanol, a new brominated and sulfated pimarane diterpene was isolated from the Caribbean sponge Tedania ignis. Structure of tedanol was elucidated by mass spectroscopy and extensive NMR studies (including spectral simulation), and its absolute configuration was determined using the Mosher method. Tedanol showed a potent anti-inflammatory activity at 1 mg/kg evaluated in vivo in a mouse model of inflammation. After a single intraperitoneal administration, tedanol significantly reduced both the acute and the subchronic phases of carrageenan-induced inflammation. The anti-inflammatory activity was coupled with a strong inhibition of COX-2 expression, inhibition of cellular infiltration measured as mieloperoxidase (MPO) levels, and inhibition of iNOS expression. These features make tedanol a promising template for the development of new anti-inflammatory molecules with low gastrointestinal toxicity. Tedanol, a new brominated and sulfated pimarane diterpene from the Caribbean sponge Tedania ignis, showed a potent in vivo anti-inflammatory activity at 1 mg/kg in a mouse model of inflammation.