Acetylated Sesterterpenes from the Great Barrier Reef Sponge Luffariella variabilis

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 4; pp. 648 - 651
• Main Authors: Ettinger-Epstein, Piers, Motti, Cherie A, de Nys, Rocky, Wright, Anthony D, Battershill, Christopher N, Tapiolas, Dianne M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2007; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Alkynes - chemistry; Alkynes - isolation & purification; Animals; Biological and medical sciences; Chemistry, Medicinal; General pharmacology; Life Sciences & Biomedicine; Luffariella; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Porifera - chemistry; Science & Technology; Sesterterpenes; Terpenes - chemistry; Terpenes - isolation & purification; Australia; Oceania; Great Barrier Reef; Terpenoid; Cyclohexane derivatives; Aliphatic compound; Pharmacognosy; Animal origin; Hemiacetal; Enaldehyde; Marine environment; Tissue; Porifera; Acylal; Isolation; Invertebrata; Secondary alcohol; Sesterterpenes; Monocyclic compound; Cyclopentane derivatives; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np060240d

Chemical investigation of the sponge Luffariella variabilis collected from the Palm Island group of the Great Barrier Reef, Australia, yielded three new acetylated compounds, 25-acetoxyluffariellin A (1), 25-acetoxyluffariellin B (2), and 25-acetoxyseco-manoalide (3). The structures of the new compounds were elucidated on the basis of interpretation of their spectroscopic data. The known metabolites manoalide (4), seco-manoalide (5), luffariellin A (8), and manoalide monoacetate (10) were also isolated. The new acetylated compounds (1−3) were labile in the sponge tissue when samples were allowed to thaw prior to extraction, but were stable once isolated. Sponge samples that were completely thawed contained only hydroxylated compounds (alcohols). This finding supported the deduction that the acetylated compounds are being enzymatically transformed and/or degraded.