Guttiferone F, the First Prenylated Benzophenone from Allanblackia stuhlmannii

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 1; pp. 130 - 132
• Main Authors: Fuller, Richard W, Blunt, John W, Boswell, Jamie L, Cardellina, John H, Boyd, Michael R
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 1999; Glendale, AZ American Society of Pharmacognosy
• Subjects: ACIDE BENZOIQUE; ACIDO BENZOICO; AIDS/HIV; Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; ANTIMICROBIAL PROPERTIES; ANTIVIRAL PROPERTIES; BENZOIC ACID; Benzophenones - chemistry; Benzophenones - isolation & purification; Benzophenones - pharmacology; Biological and medical sciences; BOIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CLUSIACEAE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; DERIVATIVES; DRUG PLANTS; ESPECTROMETRIA; ESTRUCTURA QUIMICA; General pharmacology; GENERO HUMANO; GENRE HUMAIN; GUTTIFERAE; HERPETOVIRIDAE; HUMAN IMMUNODEFICIENCY VIRUS; MADERA; Magnetic Resonance Spectroscopy; MANKIND; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; PLANTAS MEDICINALES; PLANTE MEDICINALE; Plants - chemistry; PROPIEDADES ANTIMICROBIANAS; PROPRIETE ANTIMICROBIENNE; RACINE; RAICES; ROOTS; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrometry, Mass, Fast Atom Bombardment; STRUCTURE CHIMIQUE; TANZANIA; TANZANIE; WOOD; Wood; Root; Pharmacognosy; Guttiferae; Enol; Retroviridae; Lentivirus; Diphenols; Medicinal plant; Virus; Ketophenols; Triketone; Dicotyledones; Angiospermae; Plant origin; Bicyclic compound; Antiviral; Benzenic compound; Isolation; Spermatophyta; Human immunodeficiency virus; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9801514

The HIV-inhibitory activity in extracts of Allanblackia stuhlmannii was tracked, via bioassay-guided fractionation, to a new member of the camboginol/guttiferone class of prenylated benzophenones, guttiferone F (1). The structure was solved by extensive NMR analyses and by acid-catalyzed conversion to 30-epi-cambogin (4). This is the first report of this compound type in the genus Allanblackia.