Quinolactacins A, B and C. Novel Quinolone Compounds from Penicillium sp. EPF-6. I. Taxonomy, Production, Isolation and Biological Properties.

Kakinuma, Norihiro; Iwai, Hiroki; Takahashi, Senji; Hamano, Kunikatsu; Yanagisawa, Tadashi; Nagai, Koji; Tanaka, Kōichi; Suzuki, Kenichi; Kirikae, Fumiko; Kirikae, Teruo; Nakagawa, Akira

doi:10.7164/antibiotics.53.1247

Cited by 45 publications

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“…From this strain, three different natural products were isolated, which included the rather frequently occurring cladosporin (Figure 7, 17) (Reese et al 1988), and also the structurally unusual tetramic acid derivatives quinolactacin A1 (Figure 7, 18) ) and A2 (Figure 7, 19) . The latter two compounds were previously isolated from the genus Penicillium and have recently aroused interest due to their inhibitory activity against TNF-a production by macrophages that had been stimulated by LPS (Kakinuma et al 2000), as well as their inhibitory activity against acetylcholinesterase . While TNF-a is involved in inflammations and may even lead to septic shock, acetylcholinesterases are interesting drug targets for the treatment of neurodegenerative disorders, such as Alzheimer's disease.…”

Section: ) the Amino Acid Sequence Of The Peptide Is Cyclo(l-leumentioning

confidence: 99%

Sponge-associated fungi and their bioactive compounds: the Suberites case

Proksch

Ebel

Edrada

et al. 2008

Botm

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Specimens of Suberites domuncula that had been cultured in aquaria for 4 weeks were analyzed for their associated fungi. A total of 81 fungal strains belonging to 20 different genera was isolated and identified by morphological and molecular methods. The most frequently isolated taxa were Cladosporium spp., Penicillium spp., Petriella sp., Phialophora spp. and Engyodontium album. Based on chromatographic and mass spectrometric analysis of fungal extracts, as well as on bioassay results, Aspergillus ustus, Penicillium sp., Petriella sp. and Scopulariopsis sp. were selected for in-depth analysis of their natural products. A total of 19 different fungal metabolites, including three new natural products, was isolated and structurally identified. A. ustus yielded two sesquiterpenes, a drimane derivative and deoxyuvidin, as well as a sesterterpene ophiobolin H. The drimane derivative had an ED 50 value against L5178Y cells of 1.9 mg ml -1 in vitro. The crude extract of Petriella sp. was also strongly cytotoxic against the L5178Y cell line. The cyclic tetrapeptide WF-3161 was primarily responsible for the activity; the ED 50 value was -0.1 mg ml -1. It was identical to the known compound WF-3161 and had been previously isolated from Petriella guttulata. In addition to WF-3161, three further natural products were obtained and unequivocally identified as new derivatives of infectopyrone by one-and two-dimensional NMR spectroscopy and by . Penicillium sp. yielded the largest number of metabolites. Viridicatin, viridicatol, cyclopenin and cyclopenol suppressed larval growth of the polyphagous pest insect Spodoptera littoralis when incorporated into an artificial diet at an arbitrarily chosen concentration of 237 ppm. Viridicatol was the most active compound and had an ED 50 value of ca. 50 ppm. Scopulariopsis sp. yielded three metabolites, including the known acetylcholinesterase inhibitors quinolactacin A1 and A2.

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Section: ) the Amino Acid Sequence Of The Peptide Is Cyclo(l-leumentioning

confidence: 99%

Sponge-associated fungi and their bioactive compounds: the Suberites case

Proksch

Ebel

Edrada

et al. 2008

Botm

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“…In addition, novel quinolone alkaloids, quinolactacins A (1), B (2), and C (3) were obtained from the cultured broth of Penicillium sp. EPF-6, which was isolated from the larvae of the mulberry pyralid (Margaronia pyloalis Welker) [10]. Alkaloid 1, the major constituent, exhibited inhibitory activity against tumor necrosis factor (TNF) production by murine macrophages and macrophage-like J774.1 cells stimulated with lipopolysaccharide (LPS).…”

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confidence: 99%

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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Quinolactacins, which inhibit tumor necrosis factor production, contain a quinolone skeleton conjugated with a g -lactam. The biosynthesis of quinolactacin was investigated by feeding experiments using 13 Keywords quinolactacin, quinolone, biosynthesis, 13 C labeled precursor, Penicillium sp. IntroductionSince entomopathogenic fungi possess a parasitic function, it was expected that novel biologically active compounds such as insecticides and immunosuppressants would be isolated from them [1ϳ7]. In the course of an HPLC-based, chemical screening program of the metabolites of entomopathogenic fungi, the novel pyridone alkaloids, pyridovericin and pyridomacrolidin, possessing protein kinase inhibitory activity, were isolated from the cultured broth of Beauveria bassiana 9]. In addition, novel quinolone alkaloids, quinolactacins A (1), B (2), and C (3) were obtained from the cultured broth of Penicillium sp. EPF-6, which was isolated from the larvae of the mulberry pyralid (Margaronia pyloalis Welker) [10]. Alkaloid 1, the major constituent, exhibited inhibitory activity against tumor necrosis factor (TNF) production by murine macrophages and macrophage-like J774.1 cells stimulated with lipopolysaccharide (LPS).Quinolactacins have a unique quinolone skeleton conjugated with a g-lactam ring [11], as shown in Figure 1. Subsequently, Kim et al., reported the characterization of stereoisomers of 1 through a screening program for inhibitors of acetylcholinesterase [12], and Tatsuta's group reported the biomimetic synthesis of quinolactacin B (2) using acetic acid, valine, and anthranilic acid [13]. In this paper, the biosynthesis of 1 was studied by feeding experiments using several 13 C single-labeled precursors and D-[U-

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“…The fraction DLM212-MB was separated by HPLC using a C 18 (19). 27 HPLC-UV-MS analysis of the fraction DLM212-MB4 (9.0 mg) indicated a major peak with l max 224 and 283 nm in the UV spectrum, and a peak with m/z 298.3 in the mass spectrum, corresponding to the [M+H] + ion of (20). Purification of (20) O + 0.1% formic acid; flow rate of 1.0 mL/min; detection at l max 254 and 280 nm) yielded 2.0 mg of DLM212-MC2E.…”

Section: Isolation and Identification Of Fungal Secondary Metabolitesmentioning

confidence: 99%

“…HPLC-UV-MS analysis of this fraction indicated a major peak with l max 218, 250 and 316 nm in the UV spectrum, and a peak with m/z 287.0 in the mass spectrum, corresponding to the [M+H] + ion of the quinolactacin C (22). 27 Roussoella sp. DLM33, isolated from the ascidian Didemnum ligulum, was grown in 10 L of 3% malt extract medium (as described above).…”

Section: Isolation and Identification Of Fungal Secondary Metabolitesmentioning

confidence: 99%

“…HPLC-UV-MS analysis of the fraction F56-A2(4) (32.9 mg) indicated a major peak with l max 261 nm in the UV spectrum, and a peak with m/z 287.3 in the mass spectrum, corresponding to the [M+H] + ion of 25. HPLC purification of (25) (26) 33 and of 1.0 mg of anofinic acid (27). 33 HPLC-UV-MS analysis of fraction F56-A4(2) indicated a major peak with l max 240, 279 and 347 nm in the UV spectrum, and a peak with m/z 209.07 in the mass spectrum, corresponding to the [M+H] + ion of (28).…”

Section: Isolation and Identification Of Fungal Secondary Metabolitesmentioning

confidence: 99%

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A Strategy for the Rapid Identification of Fungal Metabolites and the Discovery of the Antiviral Activity of Pyrenocine a and Harzianopyridone

Ióca¹,

Romminger²,

Santos³

et al. 2016

Química Nova

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The isolation and identification of bioactive metabolites from complex extracts obtained from microbial growth media is a time consuming, costly, and labor-intensive task. A strategy to rapidly identify secondary metabolites isolated from extracts obtained from the culture media of marine-derived and endophytic fungal strains is described. Identification was achieved by HPLC-UV-MS and 1 H NMR analyses in combination with data obtained from the Dictionary of Natural Products. Among the compounds identified, (-)-naphthoquinoneimine, citreorosein, emodin, pyrenocine A and harzianopyridone displayed moderate to potent antiviral activity. (-)-Naphthoquinoneimine was isolated as the enantiomer of its previously reported dextrorotatory congener, while 6,7-dihydroxy-2,2-dimethyl-4-chromanone is herein reported for the first time as a natural product.

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Quinolactacins A, B and C. Novel Quinolone Compounds from Penicillium sp. EPF-6. I. Taxonomy, Production, Isolation and Biological Properties.

Cited by 45 publications

References 0 publications

Sponge-associated fungi and their bioactive compounds: the Suberites case

Sponge-associated fungi and their bioactive compounds: the Suberites case

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

A Strategy for the Rapid Identification of Fungal Metabolites and the Discovery of the Antiviral Activity of Pyrenocine a and Harzianopyridone

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