Efficient synthesis of 9,10-dihydropyrano[2,3-<i>h</i>]chromene-2,8-dione derivatives in ionic liquid and the study of their antioxidant activity

Lasemi, Zahra; Azimi, Razieh; Amiri, Mohammadreza Azizi

doi:10.1080/14786419.2016.1166493

Cited by 23 publications

(13 citation statements)

References 21 publications

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“…OMF is a well-known γ-pyrone derivative previously isolated from Talaromyces spp. 25 , 26 , and it was the most abundant secondary metabolite biosynthesized by F36CF in single culture (Fig. 1 , peak at 10.5 min).…”

Section: Resultsmentioning

confidence: 93%

“…1 , peak at 10.5 min). OMF exhibited notable antibiotic and antitumor properties 27 , 28 , and recently an insecticidal effect has also been observed 26 , thus expanding the range of its biological activities. Herquline B, earlier purified from a strain of Penicillium herquei , is a nitrogen-containing metabolite acting as platelet anti-aggregation factor 29 .…”

Section: Resultsmentioning

confidence: 99%

“…The plates were incubated at 25 °C and fungal plugs were transferred into fresh plates until pure endophyte culture was obtained. The fungus was identified according to morphological characters and molecular analyses using primers for rDNA-ITS and β-tubulin gene sequences 26 .…”

Section: Methodsmentioning

confidence: 99%

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Co-Culture of Plant Beneficial Microbes as Source of Bioactive Metabolites

Vinale

Nicoletti

Borrelli

et al. 2017

Sci Rep

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In microbial cultures the production of secondary metabolites is affected by experimental conditions, and the discovery of novel compounds is often prevented by the re-isolation of known metabolites. To limit this, it is possible to cultivate microorganisms by simulating naturally occurring interactions, where microbes co-exist in complex communities. In this work, co-culturing experiments of the biocontrol agent Trichoderma harzianum M10 and the endophyte Talaromyces pinophilus F36CF have been performed to elicit the expression of genes which are not transcribed in standard laboratory assays. Metabolomic analysis revealed that the co-culture induced the accumulation of siderophores for both fungi, while production of M10 harzianic and iso-harzianic acids was not affected by F36CF. Conversely, metabolites of the latter strain, 3-O-methylfunicone and herquline B, were less abundant when M10 was present. A novel compound, hereby named harziaphilic acid, was isolated from fungal co-cultures, and fully characterized. Moreover, harzianic and harziaphilic acids did not affect viability of colorectal cancer and healthy colonic epithelial cells, but selectively reduced cancer cell proliferation. Our results demonstrated that the co-cultivation of plant beneficial fungi may represent an effective strategy to modulate the production of bioactive metabolites and possibly identify novel compounds.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

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Co-Culture of Plant Beneficial Microbes as Source of Bioactive Metabolites

Vinale

Nicoletti

Borrelli

et al. 2017

Sci Rep

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“…The organosulphur dipeptides in Allium are of special value considering that they are the mediators of its medicinal use and organoleptic characters. Particularly, garlic is enriched in γ-glutamyl peptides and sulfoxides [ 12 ]. The main organosulphur compounds detected in garlic were N -γ-glutamyl- S -allylcysteine, N -γ-glutamyl- S -allylthiocysteine, allithiamine and N -hexosyl- N -γ-glutamyl- S -allylcysteine identified in peaks L6/10, L8/15, L13, and L5.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Profiles and Antimicrobial Activities of Allium cepa Red cv. and A. sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics

et al. 2017

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Plants of the Allium genus produce sulphur compounds that give them a characteristic (alliaceous) flavour and mediate for their medicinal use. In this study, the chemical composition and antimicrobial properties of Allium cepa red cv. and A. sativum in the context of three different drying processes were assessed using metabolomics. Bulbs were dried using either microwave, air drying, or freeze drying and further subjected to chemical analysis of their composition of volatile and non-volatile metabolites. Volatiles were collected using solid phase micro-extraction (SPME) coupled to gas chromatography–mass spectrometry (GC/MS) with 42 identified volatiles including 30 sulphur compounds, four nitriles, three aromatics, and three esters. Profiling of the polar non-volatile metabolites via ultra-performance liquid chromatography coupled to high resolution MS (UPLC/MS) annotated 51 metabolites including dipeptides, flavonoids, phenolic acids, and fatty acids. Major peaks in GC/MS or UPLC/MS contributing to the discrimination between A. sativum and A. cepa red cv. were assigned to sulphur compounds and flavonoids. Whereas sulphur conjugates amounted to the major forms in A. sativum, flavonoids predominated in the chemical composition of A. cepa red cv. With regard to drying impact on Allium metabolites, notable and clear separations among specimens were revealed using principal component analysis (PCA). The PCA scores plot of the UPLC/MS dataset showed closer metabolite composition of microwave dried specimens to freeze dried ones, and distant from air dried bulbs, observed in both A. cepa and A. sativum. Compared to GC/MS, the UPLC/MS derived PCA model was more consistent and better in assessing the impact of drying on Allium metabolism. A phthalate derivative was found exclusively in a commercial garlic preparation via GC/MS, of yet unknown origin. The freeze dried samples of both Allium species exhibited stronger antimicrobial activities compared to dried specimens with A. sativum being in general more active than A. cepa red cv.

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“…The study also found that the combination of the essential oil with fluconazole resulted in significant synergistic effects. Vitali et al [ 43 ] demonstrated that the essential oil of Carpathian thymus , which had nerolidol as a major component, presented significant antifungal activities both alone and associated with nystatin. Of note, this is to date, the first study reporting the antifungal properties of liposomal nerolidol.…”

Section: Discussionmentioning

confidence: 99%

Antifungal Properties of Nerolidol-Containing Liposomes in Association with Fluconazole

et al. 2020

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(1) Background: Infections by Candida species represent a serious threat to the health of immunocompromised individuals. Evidence has indicated that nerolidol has significant antifungal properties. Nonetheless, its use is restricted due to a low water solubility and high photosensitivity. The incorporation into liposomes may represent an efficient alternative to improve the physicochemical and biopharmaceutical properties of this compound. The present study aimed to characterize the antifungal properties of liposomal nerolidol, alone or in combination with fluconazole. Of note, this is the first study reporting the antifungal activity of liposomal nerolidol and its potentiating effect in association with fluconazole. (2) Methods: The Inhibitory Concentration 50%-IC50 and minimum fungicide concentrations (MFC) of the substances against Candida albicans (CA), Candida tropicalis (CT), and Candida krusei (CK) were established by subculture in a solid medium. To evaluate the antifungal-enhancing effect, the MFC of fluconazole was determined in the presence or absence of subinhibitory concentrations of nerolidol (free or liposomal). The analysis of fungal dimorphism was performed through optical microscopy and the characterization of liposomes was carried out considering the vesicular size, polydispersion index, and zeta medium potential, in addition to a scanning electron microscopy analysis. (3) Results: The physicochemical characterization revealed that liposomes were obtained as homogenous populations of spherical vesicles. The data obtained in the present study indicate that nerolidol acts as an antifungal agent against Candida albicans and Candida tropicalis, in addition to potentiating (only in the liposomal form) the effect of fluconazole. However, the compound had little inhibitory effect on fungal dimorphism. (4) Conclusions: The incorporation of nerolidol into liposomes improved its antifungal-modulating properties.

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Efficient synthesis of 9,10-dihydropyrano[2,3-h]chromene-2,8-dione derivatives in ionic liquid and the study of their antioxidant activity

Cited by 23 publications

References 21 publications

Co-Culture of Plant Beneficial Microbes as Source of Bioactive Metabolites

Co-Culture of Plant Beneficial Microbes as Source of Bioactive Metabolites

Phytochemical Profiles and Antimicrobial Activities of Allium cepa Red cv. and A. sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics

Antifungal Properties of Nerolidol-Containing Liposomes in Association with Fluconazole

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