Isomeric Furanosesquiterpenes from the Portuguese Marine Sponge Fasciospongia sp

• Published in: Journal of natural products (Washington, D.C.) Vol. 71; no. 12; pp. 2049 - 2052
• Main Authors: Gaspar, Helena, Santos, Susana, Carbone, Marianna, Rodrigues, Ana Sofia, Rodrigues, Ana Isabel, Uriz, Maria J, Savluchinske Feio, Sónia Murta, Melck, Dominique, Humanes, Madalena, Gavagnin, Margherita
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.12.2008; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Animals; Biological and medical sciences; Chemistry, Medicinal; Furans - chemistry; Furans - isolation & purification; General pharmacology; Life Sciences & Biomedicine; Marine Biology; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Porifera - chemistry; Portugal; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Stereoisomerism; Portugal; Europe; ANTIBACTERIAL; NUDIBRANCH DORIOPSILLA-AREOLATA; PALLESCENSIN-A; CACOSPONGIONOLIDE; Terpenoid; Five membered ring; Pharmacognosy; Relative configuration; Epimer; Animal origin; Tricyclic compound; Oxygen heterocycle; In vitro; Biological activity; Marine environment; Porifera; Sesquiterpenes; Isolation; Invertebrata; Antibacterial agent; Monocyclic compound; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800346c

This paper reports the chemical study of a sample of Fasciospongia sp. collected along the Atlantic Portuguese coast. Three new isomeric furanosesquiterpenes, isomicrocionin-3 (1), (−)-microcionin-1 (2), and (−)-isomicrocionin-1 (3), were isolated along with the known (−)-ent-pallescensin A (4) and (−)-pallescensin-1 (5) from the ethyl acetate-soluble portion of the methanolic extract. The structures of the new compounds were elucidated by extensive spectroscopic studies. (−)-Microcionin-1 (2) tested positive against several Gram-negative bacteria.