Penitholabene, a rare 19-nor labdane-type diterpenoid from the deep-sea-derived fungus Penicillium thomii YPGA3

Chemical examination of the fermented material of the deep-sea-derived fungus Penicillium thomii YPGA3 led to the identification of a rare 19-nor labdane-type diterpenoid, named penitholabene (1). The structure was elucidated based on extensive analyses of the spectroscopic data and quantum chemical calculations of the C-13 NMR and ECD data. A synthetic compound from commercial sources with the same planar structure is recorded in SciFinder (CAS number: 1217878-75-5), but there is no related reference and the configurations of chiral centers and double bond are not depicted. Penitholabene was reported as a new compound in the current study. To our knowledge, Penitholabene represents the first 19-nor labdane-type diterpenoid found in nature. It showed inhibitory effect against alpha-glucosidase with an IC50 value of 282 mu M, being more active than the positive control acarbose (1.33 mM).