title: Structures and biomimetic synthesis of novel α-pyrone polyketides of an endophytic Penicillium sp. in Catharanthus roseus.
abstract: Novel polyketides, citreoviripyrone A (1) and B (2), known citreomontanin (3), and (-)-citreoviridin (4) were isolated from the mycelium of the endophytic fungus. The endophytic fungus, which belongs to the genus Penicillium, was separated from surface-sterilized healthy leaves of Catharanthus roseus. The structures of 1 and 2 were determined on the basis of NMR data, and 1 was characterized as an α-pyrone polyketide featuring bicyclo[4.2.0]octadiene. The biomimetic synthesis of 1 and 2 from 3 elucidated a plausible biosynthetic pathway. Both Zn(II)-type and NAD(+)-dependent histone deacetylase inhibitors significantly enhanced the production of 1 and 3.
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-yama, Aoba-ku, Sendai 980-8578, Japan. tasai@m.tohoku.ac.jp
authors: Teigo
authors: T
authors: Asai
authors: Dan
authors: D
authors: Luo
authors: Kouwa
authors: K
authors: Yamashita
authors: Yoshiteru
authors: Y
authors: Oshima
mesh_terms: D001313:Aurovertins / Q000737:chemistry / Q000302:isolation & purification; D030008:Catharanthus / Q000382:microbiology*; D056572:Histone Deacetylase Inhibitors / Q000494:pharmacology; D015080:Mesna / Q000494:pharmacology; D015394:Molecular Structure; D009243:NAD / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D018515:Plant Leaves / Q000382:microbiology; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D001313:Aurovertins; D056572:Histone Deacetylase Inhibitors; D061065:Polyketides; D011753:Pyrones; D009243:NAD; C030922:citreomontanine; D015080:Mesna; C014416:citreoviridin