The Berkeleyamides, Amides from the Acid Lake FungusPenicillum rubrum

Abstract

We previously reported several novel bioactive hybrid polyketide-terpenoid metabolites from a deep water Penicillium rubrum isolated from Berkeley Pit Lake, Butte, Montana. In this paper we report the structures of four new amides, berkeleyamides A-D (1, 4, 5, 7), isolated from extracts of this fungus. The structures of these compounds were deduced by analysis of NMR data, chemical derivatization, and comparison of their spectroscopic data to those of known compounds.

Lactone Derivatives from the Marine-Derived Fungus Penicillium sp. PSU-F44

“…PSU-F44, isolated from a sea fan Annella sp., exhibited antibacterial activity against a clinical isolate of methicillinresistant Staphylococcus aureus (MRSA) SK1 and a clinical isolate of Microsporum gypseum (MG) SH-MU-4 with the respective minimum inhibitory concentration (MIC) values of 320 and 160 mg/ml. We report herein the isolation of one new pyrone, penicipyrone (1), and one new g-lactone, penicilactone (2), together with three known macrolides, (ϩ)-brefeldin A (3), 8) (ϩ)-brefeldin C (4), 9) and 7-oxobrefeldin A (5) 10) from this extract. Their antimicrobial activities against MRSA SK1 and MG SH-MU-4 were evaluated.…”

“…The fungi in the genus Penicillium have produced a variety of compounds, for example, polyketide-terpenoid, 1) alkaloid, 2) lactone, 3) and quinone derivatives. 4) Some of these exhibit a wide range of biological and pharmacological activities, e.g., anticancer penicidones, 2) antifungal botryodiplodin, 5) antibacterial rugulotrosins, 6) and antioxidant pennicitrinone.…”

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.…”

Nature: a vital source of leads for anticancer drug development

“…Novel sesquiterpenoid and polyketide-terpenoid metabolites, berkeleydione and berkeleytrione, and berkeleyamides A-D (Fig. 6), showing inhibition against metalloproteinase-3 and caspase-1, activities relevant to cancer, have been isolated from Penicillium rubrum Stoll found in the polluted waters of Berkeley Pit Lake in Montana (Stierle et al 2008). …”