Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity

Abourashed, Ehab A.; Mikell, Julie Rakel; Khan, Ikhlas A.

doi:10.1016/j.bmc.2012.03.046

Cited by 33 publications

(18 citation statements)

References 21 publications

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“…Cunninghamella species afforded Phase II metabolites identified as 2,3-dehydrosilybin-3-O-β-D-glucoside and silybin-7-sulfate and 2,3-dehydrosilybin-7-sulfate. The antioxidant activity of 2,3-dehydrosilybin-7-sulfate more than doubled in comparison with the activity of the parent compound [189].…”

Section: Microbial Transformations For Providing Information Regardinmentioning

confidence: 89%

Microbial Transformations of Plant Secondary Metabolites

Mutafova¹,

Fernandes²,

Mutafov³

et al. 2016

Bioprocessing of Plant in Vitro Systems

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The aim of this chapter is to present the authors' view on the place and role of microbial transformation reactions as a perspective means of processing of plantderived biologically active compounds into metabolites with new and/or increased activity and availability and decreased toxicity. Some microbial transformations providing information regarding metabolism in humans and mammals of plant-derived secondary metabolites applied as drugs and/or food additives are also considered.

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Section: Microbial Transformations For Providing Information Regardinmentioning

confidence: 89%

Microbial Transformations of Plant Secondary Metabolites

Mutafova¹,

Fernandes²,

Mutafov³

et al. 2016

Bioprocessing of Plant in Vitro Systems

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“…Penicillium albidum (AM79) dihydroxylated the Δ 2″(3″) double bond of xanthohumol to produce 3 0 -[3″-hydroxy-3″-methylbutyl]-4,2 0 ,4 0 -trihydroxy-6 0 -methoxychalcone (199, 22.84%) (Figure 19). significantly decreased the DPPH free radical scavenging potential; however, further dehydrogenation Δ 2 (3) to 2,3-dehydrosilbyn-7-sulfate (206) drastically enhanced the DPPH free radical scavenging potential activity [109] (Figure 21).…”

Section: Flavonoidsmentioning

confidence: 99%

Microorganisms as Biocatalysts and Enzyme Sources

Cano-Flores¹,

Gómez²,

Escalona-Torres³

et al. 2020

Microorganisms

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Microbial-catalyzed biotransformations have considerable potential for the generation of an enormous variety of structurally diversified organic compounds, especially natural products with complex structures like triterpenoids, flavonoids, steroids, steroidal saponins, and sesquiterpenoids. They offer efficient and economical ways to produce semisynthetic analogues and novel lead molecules. Microorganisms such as bacteria and fungi could catalyze chemo-, regio-, and stereospecific hydroxylations of diverse substrates that are extremely difficult to produce by chemical routes. During recent years, considerable research has been performed on the microbial transformation of bioactive compounds, in order to obtain biologically active molecules with diverse structural features. In green chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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“…Radical scavenging activity was determined by modifying method by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay 25,26 . The assay solution consisted of 100 mL of (150 mM) 2,2-diphenyl-1-picrylhydrazyl (DPPH), 20 mL of increasing concentration of test compounds and the volume was adjusted to 200 mL in each well with DMSO.…”

Section: Free Radical Scavenging Assaymentioning

confidence: 99%

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

Ashraf

Rafiq

Seo

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of umbelliferone analogues were synthesized and their inhibitory effects on the DPPH and mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant mushroom tyrosinase inhibitory activities. Especially, 2-oxo-2-[(2-oxo-2H-chromen-7-yl)oxy]ethyl-2,4-dihydroxybenzoate (4e) bearing 2,4-dihydroxy substituted phenyl ring exhibited the most potent tyrosinase inhibitory activity with IC 50 value 8.96 mM and IC 50 value of kojic acid is 16.69. The inhibition mechanism analyzed by LineweaverBurk plots revealed that the type of inhibition of compound 4e on tyrosinase was noncompetitive. The docking study against tyrosinase enzyme was also performed to determine the binding affinity of the compounds. The compounds 4c and 4e showed the highest binding affinity with active binding site of tyrosinase. The initial structure activity relationships (SARs) analysis suggested that further development of such compounds might be of interest. The statistics of our results endorses that compounds 4c and 4e may serve as a structural template for the design and development of novel tyrosinase inhibitors.

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Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity

Cited by 33 publications

References 21 publications

Microbial Transformations of Plant Secondary Metabolites

Microbial Transformations of Plant Secondary Metabolites

Microorganisms as Biocatalysts and Enzyme Sources

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

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