8,15-Epoxylabdane and norlabdane diterpenoids from Eragrostis viscosa

• Published in: Phytochemistry (Oxford) 2010-05, Vol.71 (7), p.798-803
• Main Authors: Sebastião, N’Soki N., Cordeiro, Inês J.S., dos Santos, Aldenir F., Gaspar, Jorge F., Martins, Célia, Rueff, José, Diakanamwa, Carlos, Sant’Ana, Antônio E.G., de Mendonça, Dina I.M.D.
• Format: Article
• Language: English
• Subjects: 8,15-Epoxylabdanes; Animals; Biological and medical sciences; Biomphalaria glabrata; chemical constituents of plants; Chemical constitution; chemical structure; Clastogenic activity; Crystallography, X-Ray; Diterpenes; Diterpenes - analysis; diterpenoids; Eragrostis; Eragrostis - chemistry; Eragrostis viscosa; Fundamental and applied biological sciences. Psychology; labdane diterpene; Magnetic Resonance Spectroscopy; Models, Molecular; molluscicidal properties; Molluscicide activity; Mutagenic activity; mutagenicity; Plant physiology and development; Poaceae; Snails; spectral analysis; stereochemistry
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2010.02.003

Four labdanes with a 8α,15-epoxy ring, were isolated from the hexane extract of the aerial parts of Eragrostis viscosa. The extract presented moderate activity against Biomphalaria glabrata. 8α,15-Epoxylabdan-16β-oic acid 1 showed no mutagenic activity and no significant clastogenic activity. Four labdanes with a 8α,15-epoxy ring (8α,15-epoxylabdan-16β-oic acid; 8α,15-epoxy-16-norlabdan-13-one; 8α,15-epoxy-16-norlabdane; and 16-acetoxy-8α,15-epoxylabdane) and the known compound ambreinolide were isolated from the hexane extract of the aerial parts of the grass Eragrostis viscosa. The structures of all compounds were established based on spectroscopic data and the X-ray analysis of 8α,15-epoxy-16-norlabdan-13-one. The hexane extract presented moderate activity against the snail Biomphalaria glabrata. 8α,15-Epoxylabdan-16β-oic acid showed no mutagenic activity for doses up to 1000 μg/plate and no significant clastogenic activity for doses up to 100 μg/ml.