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

Abstract

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 ¹³C 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 α-glucosidase with an IC₅₀ value of 282 μM, being more active than the positive control acarbose (1.33 mM).

Keywords: 19-Nor labdane; Isolation and identification; Penicillium thomii YPGA3; α-Glucosidase.