Azaphilones: Chemistry and Biology

Gao, Jin‐Ming; Shen, Yang; Qin, Jianchun

doi:10.1021/cr300402y

Cited by 361 publications

(351 citation statements)

References 365 publications

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“…This chain was connected to C-3 by HMBC correlations of H-9 (d H 6.24) and H-10 (d H 6.67) to C-3. Thus, compound 1 was determined as a new azaphilone derivative belonging to sclerotiorin-type compounds (Gao et al, 2013). The stereochemistry of 1 was suggested by comparisons of experimental spectroscopic data with those of 2, which are discussed below.…”

Section: Structure Elucidationmentioning

confidence: 99%

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Son

Kim

et al. 2016

Phytochemistry

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Section: Structure Elucidationmentioning

confidence: 99%

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Son

Kim

et al. 2016

Phytochemistry

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“…KCB12C078 was isolated from marine sediment in the Korea western sea region, Anmyeon Island, and chemical investigation of fungus led to the isolation of two new azaphilone derivatives, penidioxolanes A (1) and B (2), and four known azaphilones (3)(4)(5)(6). In this study, we describe the fermentation, isolation, and structural determination of these compounds, and their biological activity.…”

Section: -13mentioning

confidence: 99%

“…4 Among these various bioactive compounds, azaphilone family has been isolated from fungi belonging to 23 genera from 13 families, such as, Aspergillus, Penicillium, Chaetomium, Talaromyces, Pestalotiopsis, Phomopsis, Emericella, and Epicoccum, as well as Monascus and Hypoxylon sp.. Several azaphilones are unique to one species and constitute taxonomically important marker metabolites. 5,6 Azaphilone family are structurally diverse pigments, mostly secondary metabolites of fungal origin, and are highly oxygenated bicyclic rings showing various biological activities, including antimicrobial, antifungal, antiviral, antioxidant, cytotoxic, nematicidal and anti-inflammatory activities.…”

Section: Introductionmentioning

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 (Az) compounds are a group of fungal aromatic polyketides featuring an oxidized pyranoquinone bicyclic structure with a tertiary alcohol that is generally acylated. Az compounds display diverse biological activities that apparently involve interfering with specific protein-protein interactions (Gao et al 2013). Az is synthesized by a non-reducing fungal polyketide synthase with a reductive release domain (NR-fPKS-R) and its collaborating enzymes (Zabala et al 2012).…”

Section: Introductionmentioning

confidence: 99%

Selective production of red azaphilone pigments in a Monascus purpureus mppDEG deletion mutant

Balakrishnan

Lim

Hwang

et al. 2017

JABC

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The Monascus azaphilone (MAz) pigment is a wellknown food colorant that has yellow, orange and red components. The structures of the yellow and orange MAz differ by two hydride reductions, with yellow MAz being the reduced form. Orange MAz can be non-enzymatically converted to red MAz in the presence of amine derivatives. It was previously demonstrated that mppE and mppG are involved in the biosynthesis of yellow and orange MAz, respectively. However, ΔmppE and ΔmppG knockout mutants maintained residual production of yellow and orange MAz, respectively. In this study, we deleted the region encompassing mppD, mppE and mppG in M. purpureus and compared the phenotype of the resulting mutant (ΔmppDEG) with that of an mppD knockout mutant (ΔmppD). It was previously reported that the ΔmppD strain retained the ability to produce MAz but at approximately 10% of the level observed in the wildtype strain. A chemical analysis demonstrated that the ΔmppDEG strain was still capable of producing both yellow and orange MAz, suggesting the presence of minor MAz route(s) not involving mppE or mppG. Unexpectedly, the ΔmppDEG strain was observed to accumulate fast-eluting pigments in a reverse phase high-performance liquid chromatography analysis. A LC-MS analysis identified these pigments as ethanolamine derivatives of red MAz, which had been previously identified in an mppE knockout mutant that produces high amounts of orange MAz.Although the underlying mechanism is largely unknown, this study has yielded an M. purpureus strain that selectively accumulates red MAz.

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Azaphilones: Chemistry and Biology

Cited by 361 publications

References 365 publications

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

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

Selective production of red azaphilone pigments in a Monascus purpureus mppDEG deletion mutant

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