α-pyrones : Small molecules with versatile structural diversity reflected in multiple pharmacological activities-an update

Bhat, Zubair Shanib; Rather, Muzafar Ahmad; Maqbool, Mubashir; Lah, Hafiz Ul; Yousuf, Syed Khalid; Ahmad, Zahoor

doi:10.1016/j.biopha.2017.04.012

Cited by 57 publications

(37 citation statements)

References 89 publications

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“…queenslandicum [31] have been shown to be active against the gram-positive bacteria Micrococcus luteus and Bacillus subtilis with MIC values close to those obtained in this work. On the other hand, both natural and synthetic α-pyrones have shown antimicrobial and antifungal activity on a variety of species [44,45]. Substitutions in positions 4 and 6 of the pyrone ring may be related to this activity.…”

Section: Resultsmentioning

confidence: 99%

Identification and characterization of compounds from Chrysosporium multifidum, a fungus with moderate antimicrobial activity isolated from Hermetia illucens gut microbiota

et al. 2019

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The gut microbiota of insects is composed of a wide range of microorganisms which produce bioactive compounds that protect their host from pathogenic attack. In the present study, we isolate and identify the fungus Chrysosporium multifidum from the gut of Hermetia illucens larvae. Extract from C. multifidum culture broth supernatant showed moderate activity against a strain of methicillin-resistant Staphylococcus aureus (MRSA). Bioguided isolation of the extract resulted in the characterization of six α-pyrone derivatives (1–6) and one diketopiperazine (7). Of these compounds, 5,6-dihydro-4-methoxy-6-(1-oxopentyl)-2H-pyran-2-one (4) showed the greatest activity (IC50 = 11.4 ± 0.7 μg/mL and MIC = 62.5 μg/mL) against MRSA.

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Section: Resultsmentioning

confidence: 99%

Identification and characterization of compounds from Chrysosporium multifidum, a fungus with moderate antimicrobial activity isolated from Hermetia illucens gut microbiota

et al. 2019

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“…The known compounds in Chrysosporium genus have displayed biological activites as antitumour [44], antifungal (36, 37, 48, 49) and cytotoxic [41], only naphthaquinon-type compounds isolated from, queenslandicum [39] have been shown to be active on gram-positive bacteria Micrococcus luteus and Bacillus subtilis with MIC values close to those obtained in this work. On the other hand, both natural and synthetic α-pyrones have shown antimicrobial and antifungal activity on a variety of species [52, 53]. Substitutions in positions 4 and 6 of the pyrone ring would be related to this activity.…”

Section: Resultsmentioning

confidence: 99%

Bioactive compounds from Chrysosporium multifidum, a fungus isolated from Hermetia illucens gut microbiota

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Cabanillas

Jullian

et al. 2019

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The gut microbiota of insects contains a wide range of organisms that protect them against the attack of pathogens by releasing various types of bioactive compounds. In the present study, we report the isolation and identification of the fungus Chrysosporium multifidum as a component of the microbiota from the larval gut of Hermetia illucens. Extract from the broth culture of C. multifidum showed moderate activity on a strain of methicillin-resistant Staphylococcus aureus (MRSA). The bioguided isolation of the extract resulted in the characterization of six α-pyrone derivatives (1-6) and one diketopiperazines (7), among them 5,6-dihydro-4-methoxy-6-(1-oxopentyl)-2H-pyran-2-one (4) showed the best activity (IC50 = 11.4 ± 0.7 µg/ml and MIC = 62.5 μg/ml).

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“…The α-pyrone moiety constitutes an essential pharmacophore in many naturally occurring and synthetic bioactive compounds. Natural products featuring a α-pyrone ring are often involved in defense processes, while frequently they possess antibacterial, antifungal, antiviral, cytotoxic, phytotoxic and neurotoxic properties [ 13 , 14 ]. In 1976, when initially isolated and characterized, enterocin ( 7 ) was reported to be bacteriostatic in a disk-diffusion assay at a concentration of 4 mg/mL against Gram-positive and Gram-negative bacteria, including strains of Escherichia coli , Proteus vulgaris , Sarcina lutea , Staphylococcus aureus and Corynebacterium xerosis , but showed no activity against strains of Bacillus subtilis , Bacillus megaterium , Pseudomonas aeruginosa , Candida albicans and Penicillium chrysogenum [ 7 ].…”

Section: Resultsmentioning

confidence: 99%

α-Pyrone Polyketides from Streptomyces ambofaciens BI0048, an Endophytic Actinobacterial Strain Isolated from the Red Alga Laurencia glandulifera

et al. 2017

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Four new (1-4) and six previously reported (5-10) α-pyrone polyketides, along with benzoic acid, hydrocinnamic acid, and (E)-cinnamic acid, were isolated from the organic extract resulting from the cultivation of the algicolous strain Streptomyces ambofaciens BI0048, which in turn was isolated from the inner tissues of the red alga Laurencia glandulifera. The structure elucidation of the isolated natural products was based on extensive analysis of their spectroscopic data (NMR, MS, UV, IR). Compounds 1-10 were evaluated for their antibacterial and cytotoxic activities against two multidrug-resistant strains of Staphylococcus aureus and one strain of Escherichia coli, as well as two human cancer cell lines.

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α-pyrones : Small molecules with versatile structural diversity reflected in multiple pharmacological activities-an update

Cited by 57 publications

References 89 publications

Identification and characterization of compounds from Chrysosporium multifidum, a fungus with moderate antimicrobial activity isolated from Hermetia illucens gut microbiota

Identification and characterization of compounds from Chrysosporium multifidum, a fungus with moderate antimicrobial activity isolated from Hermetia illucens gut microbiota

Bioactive compounds from Chrysosporium multifidum, a fungus isolated from Hermetia illucens gut microbiota

α-Pyrone Polyketides from Streptomyces ambofaciens BI0048, an Endophytic Actinobacterial Strain Isolated from the Red Alga Laurencia glandulifera

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