Novel oxygenated meroterpenoids and drimane sesquiterpenoids from the sponge-derived fungus Penicillium citreonigrum

Ebel, Rainer; Rusman, Yudi; Brauers, Gernot; Proksch, Peter; Frank, Walter; Wray, Victor

doi:10.1055/s-2006-949760

Cited by 3 publications

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“…have been extensively studied as a source of bioactive metabolites. We could find only two other reports of the 6-7 A-B ring system found in berkeleydione and the berkeleyacetals: paraherquonin 6 22 and citreonigrin A, 23 which was reported in a conference abstract. Paraherquonin also possesses a similar acetal moiety, as do additional citreonigrins, which have been reported in a doctoral thesis.…”

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confidence: 82%

The Berkeleyacetals, Three Meroterpenes from a Deep Water Acid Mine Waste Penicillium

2007

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Berkeley Pit Lake is a 1500 ft. deep abandoned open-pit copper mine filled with over 1140 billion liters of acidic, metal-sulfate contaminated water. This harsh environment is proving to be a source of unusual microorganisms that produce novel bioactive compounds. We recently reported the structures of berkeleydione (1) and berkeleytrione, two novel hybrid polyketide-terpenoid metabolites isolated from a deep water Penicillium sp. growing in Berkeley Pit lake. In this paper we report the structures of three new compounds, berkeleyacetals A-C (3-5) isolated from extracts of this fungus. The structures of these compounds were deduced by comparison of mass spectral and NMR data to that of berkeleydione 1.The Berkeley Pit Lake System is part of the largest EPA Superfund site in North America. Berkeley Pit Lake contains roughly 1140 billion liters of acidic (pH 2.5), metal-sulfate rich water that sits poised at the head of the Columbia River ecosystem. 1 We are studying the secondary metabolism of the culturable microbes isolated from Pit water and sediment samples. Several interesting compounds have been isolated from these microbes based on their activities in different bioassay guided fractionation schemes. [2][3][4][5][6] One of the first microbes to be studied from this environment was isolated from a depth of 885 feet and was subsequently identified as Penicillium rubrum Stoll based on rRNA sequencing alignment data (300 base pairs). 3 The fungus was grown in acidified potato dextrose broth (pH 2.7, still) for 21 days. At harvest time the fungus was killed by the addition of MeOH, the mycelia removed by gravity filtration and the filtrate extracted with CHCl 3 . The CHCl 3 extract inhibited both MMP-3 and caspase-1 in assay systems so it was fractionated by LH-20 column chromatography followed by HPLC to yield berkeleydione (1) and berkeleytrione (2). 3 The 1 H NMR spectra from all of the column fractions were examined for evidence of related analogs. Promising candidates were purified and tested for activity. The three new berkeleyacetals 3-5 were isolated based on this "NMR guided" fractionation as well as their activity in both enzyme bioassays. We report here the isolation and characterization of berkeleyacetals A-C, (3-5). The structures were established based upon extensive spectroscopic data and a single crystal X-ray structure for 1.We are exploring the possibility of isolating compounds with anticancer potential using in vitro signal transduction bioassay systems. Two enzyme inhibition schemes have shown promising correlation to the National Cancer Institutes Developmental Therapeutics Program human cancer cell line assay. To date, compounds isolated in our lab based on these assays have shown activity against non-small cell lung cancer 3 and ovarian cancer 4 . Matrix metalloproteinases (MMP) hydrolyze the extracellular matrix of connective tissues and basement membranes. 7, 8 MMP-3 is up-regulated in many tumors 9, 10 and can induce *To whom correspondence should be addressed. Tel: (406) Casp...

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confidence: 82%

The Berkeleyacetals, Three Meroterpenes from a Deep Water Acid Mine Waste Penicillium

2007

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“…Stierle & Stierle two reports in the literature of the six-seven A-B ring system found in berkeleydione and the berkeleyacetals: paraherquonin (20) [39] and citreonigrin A, which was reported in a conference abstract [40]. Paraherquonin also possesses a similar acetal moiety, as do the citreonigrins [41].…”

Section: Berkeleyacetalsmentioning

confidence: 99%

“…Phomopsolides A-C(33)(34)(35), E, F (36 and 37), phompyrone(38), berkbenzofuran thioester(39), phomfuranone(40), patulin (41), and dimethylphthalides 42 and 43 were all isolated from the fungal CHCl 3 extract[50]. Phomopsolide A (33) was the most active MMP-3 inhibitor with an IC 50 of 100 μM.…”

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confidence: 99%

Bioactive Secondary Metabolites from Acid Mine Waste Extremophiles

Stierle

2014

Natural Product Communications

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The extremophilic microbes of the Berkeley Pit Lake are a valuable source of new and interesting secondary metabolites. It is of particular interest that these acidophilic microbes produce small molecule inhibitors of pathways associated with low pH and high Eh. These same small molecules also inhibit molecular pathways induced by reactive oxygen species (ROS) and inflammation in mammalian cells. Low pH is a hallmark of inflammation and high Eh is one of ROS, so the suitability of this collection as a source of bioactive metabolites is actually quite biorational. Compound isolation was guided by inhibition of caspase-1 and matrix metalloproteinase-3, and active compounds were sent to the National Cancer Institute-Developmental Therapeutics Program and Memorial Sloan Kettering Cancer center for evaluation as either antiproliferative or cytotoxic agents.

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Marine Natural Products from Indonesian Waters

et al. 2019

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Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

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Novel oxygenated meroterpenoids and drimane sesquiterpenoids from the sponge-derived fungus Penicillium citreonigrum

Cited by 3 publications

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The Berkeleyacetals, Three Meroterpenes from a Deep Water Acid Mine Waste Penicillium

The Berkeleyacetals, Three Meroterpenes from a Deep Water Acid Mine Waste Penicillium

Bioactive Secondary Metabolites from Acid Mine Waste Extremophiles

Marine Natural Products from Indonesian Waters

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