日々草内生Penicillium属菌から

Org. Lett., 2013, 15 (5), pp 1020–1023  /    , DOI: 10.1021/ol303506t ,

Structures and Biomimetic Synthesis of Novel α-Pyrone Polyketides of an Endophytic Penicillium sp. in Catharanthus roseus

Teigo Asai*, Dan Luo, Kouwa Yamashita and Yoshiteru Oshima*

Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-yama, Aoba-ku, Sendai 980-8578, Japan
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

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.