Meroterpenes from Penicillium sp found in association with Melia azedarach

Berkeleyones and Related Meroterpenes from a Deep Water Acid Mine Waste Fungus That Inhibit the Production of Interleukin 1-β from Induced Inflammasomes

“…3 In our continuing studies of this extremophilic fungus 1-3 we have used signal transduction enzyme inhibition to guide the isolation of new compounds. In this case we combined bioassay-guided fractionation (inhibition of caspase-1) with NMR-guided fractionation to direct the isolation of three berkeleyone analogs ( 4 , 5 and 7 ) as well as the known compounds preaustinoid A ( 3 ) 4 and A1 ( 6 ), 5 from this fungus.…”

“…Promising candidates were purified and elucidated. The previously reported preaustinoid A ( 3) 4 and preaustinoid A1 ( 6 ) 5 as well as three new berkeleyone analogs 4, 5 and 7, were isolated by this methodology.…”

“…Comparison of the 1 H NMR and 13 C NMR spectra to those of the known compound preaustinoid A, which was also isolated from a Penicillium sp., and 3 indicated that the two compounds were identical. 4 …”

“…4 In a 2009 publication that reported the x-ray structure of preaustinoid A the authors stated that the absolute configuration of the compound was established by the optical rotation reported in the original paper and not by x-ray analysis. 13 Optical rotation is generally not sufficient to determine the absolute configuration of a molecule unless it is being compared to a molecule with a clearly defined absolute configuration.…”

Three New Polyketide−Terpenoid Hybrids from Penicillium sp.

“…8 An epoxide-initiated cyclization of a generates a tetracyclic intermediate (b), which is known as a key precursor of austin 9 and related compounds. [10][11][12] Oxidative transformations of b give rise to berkeleytrione 3 (5), recently isolated from an acid mine organism together with berkeleydione (2). Berkeleydione is supposed to be produced from the trione (5) by (i) a BaeyerVilliger type oxidation of the A-ring ketone and (ii) a 1,2-alkyl shift to form a cycloheptadiene B-ring.…”