Isochromophilone IX, a Novel GABA-Containing Metabolite Isolated from a Cultured Fungus, Penicillium sp.

Michael, Adam P.; Grace, Emily J.; Kotiw, Michael; Barrow, Russell A.

doi:10.1071/ch02021

Cited by 35 publications

(16 citation statements)

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“…It became evident that 4 , just like 1 – 3 , was a chloroazaphilone, its planar structure was determined mainly based on the 1 H– 13 C HMBC data. In comparison to NMR data of some related structures [7,9,10], our data indicated a similar isoquinoline-6,8-dione skeletal structure substituted with a 3,5-dimethyl-1,3-heptadienyl side chain. Another side chain, a (2 E )-3-methylpent-2-enedioic acid, was linked by an ester bond as found in the helicusins and a hydroxyethyl moiety as described for isochromophilone VI [9].…”

Section: Resultssupporting

confidence: 57%

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Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

et al. 2013

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Microbial studies of the Mediterranean sponge Tethya aurantium led to the isolation of the fungus Bartalinia robillardoides strain LF550. The strain produced a number of secondary metabolites belonging to the chloroazaphilones. This is the first report on the isolation of chloroazaphilones of a fungal strain belonging to the genus Bartalinia. Besides some known compounds (helicusin A (1) and deacetylsclerotiorin (2)), three new chloroazaphilones (helicusin E (3); isochromophilone X (4) and isochromophilone XI (5)) and one new pentaketide (bartanolide (6)) were isolated. The structure elucidations were based on spectroscopic analyses. All isolated compounds revealed different biological activity spectra against a test panel of four bacteria: three fungi; two tumor cell lines and two enzymes.

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Section: Resultssupporting

confidence: 57%

“…For example, isochromophilone IX has been described with MRSA activity [9], but only with an MIC value of approximately 100 μM.…”

Section: Resultsmentioning

confidence: 99%

Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

et al. 2013

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“…The EtOAc-soluble portion of the fungal extract was purified using silica gel chromatography and ODS flash column chromatography followed by reverse-phase HPLC to afford two novel fungal metabolites named penidioxolanes A (1, 1.3 mg) and B (2, 0.9 mg), together with compounds 3 (406.0 mg), 4 (0.6 mg), 5 (508.2 mg), and 6 (0.8 mg). Compounds 3-6 were identified to isochromophilone IX (3), 14 isochromophilone VI (4), 15 sclerotiorin (5), 16,17 and chloroisotiorin (6), 18 respectively, by comparing the spectroscopic data in the literature (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derivedPenicilliumsp. KCB12C078

et al. 2015

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-Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (3-6) by chemical investigation. Compounds 1 -6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.

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“…Azaphilone compounds had a wide range of bioactivities including cytotoxic, antifungal, antimicrobial, antioxidant and antiinflammatory activities, [4][5][6][7][8] and could be generally produced by Penicillium, Chaetomium and Monascus. 3 In the course of our search for novel and/or bioactive metabolites from microbes lived in special niche, 4,9,10 five azaphilones including three new isochromophilones X-XII (1-3) and two known compounds sclerotioramine (4) 11 and isochromophilone VI (5) 12 were isolated from the solid-substrate fermentation cultures of an endophytic fungus Diaporthe sp. The structures were identified on the basis of extensive spectroscopic methods.…”

Section: Introductionmentioning

confidence: 99%

Isochromophilones from an endophytic fungus Diaporthe sp.

Zang

Wei

Wang

et al. 2012

Nat. Prod. Bioprospect.

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Three new azaphilone compounds, isochromophilones X–XII ( 1–3 ), together with two known ones sclerotioramine ( 4 ) and isochromophilone VI ( 5 ) were isolated from the cultures of an endophytic fungus Diaporthe sp. The structures were elucidated by extensive HRESIMS and NMR spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines by MTT method, among which compound 1 showed moderate inhibitory effects on these cell lines. This was the first report of azaphilones isolated from Diaporthe sp. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0023-2 and is accessible for authorized users.

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Isochromophilone IX, a Novel GABA-Containing Metabolite Isolated from a Cultured Fungus, Penicillium sp.

Cited by 35 publications

References 0 publications

Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derivedPenicilliumsp. KCB12C078

Isochromophilones from an endophytic fungus Diaporthe sp.

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