Benzophenones from an Endophytic Fungus, Graphiopsis chlorocephala, from Paeonia lactiflora Cultivated in the Presence of an NAD+‑Dependent HDAC Inhibitor

• Published in: Organic letters Vol. 15; no. 8; pp. 2058 - 2061
• Main Authors: Asai, Teigo, Otsuki, Sae, Sakurai, Hiroaki, Yamashita, Kouwa, Ozeki, Tomoji, Oshima, Yoshiteru
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 19-04-2013
• Subjects: Ascomycota - chemistry; Benzophenones - chemistry; Benzophenones - isolation & purification; Benzophenones - pharmacology; Crystallography, X-Ray; Histone Deacetylase Inhibitors - chemistry; Histone Deacetylase Inhibitors - pharmacology; Molecular Conformation; NAD; Niacinamide - metabolism; Nuclear Magnetic Resonance, Biomolecular; Paeonia - microbiology; Plant Leaves - chemistry; X-Ray Diffraction
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol400781b

Graphiopsis chlorocephala was separated from the surface-sterilized healthy leaves of Paeonia lactiflora (Paeoniaceae) and cultivated with nicotinamide (an NAD+-dependent HDAC inhibitor). The culture conditions significantly enhanced secondary metabolite production in the fungus and led to the isolation of a structurally diverse set of new benzophenones, cephalanones A–F (1–6), and a known 2-(2,6-dihydroxy-4-methylbenzoyl)-6-hydroxybenzoic acid (7). The structures of 1–6 were determined from NMR data, single crystal X-ray diffraction, and chemical transformations.