New metabolites of drospirenone obtained in Mucorales fungi culture

Quintana, Paula Gabriela; Romero, Stella Maris; Vaamonde, Graciela; Baldessari, Alicia

doi:10.1016/j.molcatb.2013.08.005

Cited by 6 publications

(1 citation statement)

References 48 publications

(60 reference statements)

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“…As shown in Figure 7 A, the biotransformation was inhibited by glycerol, glycol, ethyl acetate, acetone, methanol and dimethyl sulfoxide. This fact may be attributed to a toxic effect caused by these solvents on the biomass of strain O852 [ 42 ]. The addition of ethanol had a considerable positive effect on the formation of trans -dihydrocarvone, which was indicated by an increase in the conversion ratio from 45% up to 55%.…”

Section: Resultsmentioning

confidence: 99%

Screening a Strain of Klebsiella sp. O852 and the Optimization of Fermentation Conditions for Trans-Dihydrocarvone Production

et al. 2021

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Flavors and fragrances have high commercial value in the food, cosmetic, chemical and pharmaceutical industries. It is interesting to investigate the isolation and characterization of new microorganisms with the ability to produce flavor compounds. In this study, a new strain of Klebsiella sp. O852 (accession number CCTCC M2020509) was isolated from decayed navel orange (Citrus sinensis (L.) Osbeck), which was proved to be capable of converting limonene to trans-dihydrocarvone. Besides, the optimization of various reaction parameters to enhance the trans-dihydrocarvone production in shake flask was performed for Klebsiella sp. O852. The results showed that the yield of trans-dihydrocarvone reached up to 1 058 mg/L when Klebsiella sp. O852 was incubated using LB-M medium for 4 h at 36 °C and 150 rpm, and the biotransformation process was monitored for 36 h after adding 1680 mg/L limonene/ethanol (final ethanol concentration of 0.8% (v/v)). The content of trans-dihydrocarvone increased 16 times after optimization. This study provided a basis and reference for producing trans-dihydrocarvone by biotransformation.

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Section: Resultsmentioning

confidence: 99%

Screening a Strain of Klebsiella sp. O852 and the Optimization of Fermentation Conditions for Trans-Dihydrocarvone Production

et al. 2021

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Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

2014

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A series of hydroxy‐, methoxy‐, and nitrophenylacetamides was synthesized by enzyme catalysis. The 28 new products were obtained through a lipase‐catalyzed two‐step reaction in very good to excellent yield. In the case of nitro derivatives, a one‐pot, two‐step methodology allowed the desired products to be obtained in high yields. The influence of various reaction parameters in the lipase‐catalyzed reactions, such as enzyme source, nucleophile (alcohol or amine)/substrate ratio, enzyme/substrate ratio, solvent and temperature were studied. It was observed that nitro‐substituted phenylacetates were more reactive in the aminolysis reaction than phenylacetates substituted with a hydroxyl group. To study this substituent effect, a Hammett analysis and the determination of the ρ parameter were carried out. Moreover, a computational study was applied to the most representative systems, performing an exploration of the potential energy surface for the catalyzed and noncatalyzed aminolysis reaction for nitro‐ and hydroxyphenylacetates. Both analysis showed that the presence of a strongly electron‐attracting group favors the activity of the enzyme, in complete agreement with the experimental results of the enzymatic catalysis.

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An Efficient Lipase‐Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir‐Resistant Strains

et al. 2017

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A series of eleven N‐fatty acid derivatives of vanillylamine was synthesized following an enzymatic approach, in excellent yield and a chemoselective way. The excellent results obtained by catalysis of Thermomyces lanuginosus lipase made the procedure very efficient, considering the low amount of enzyme required and its lower price in comparison with other commercial lipases. The influence of various reaction parameters in the lipase‐catalyzed reactions, such as enzyme source, nucleophile/substrate ratio, enzyme/substrate ratio, solvent and temperature, was studied. In order to evaluate the influence of the fatty acid chain length and configuration on the reaction rate and yield, HPLC analysis and molecular modeling experiments were performed. The results showed that a chain length between 12–14 carbon atoms favors the activity of the enzyme, while insaturation had no effect on the reaction rate. These facts confirm the experimental results. In addition, some of the evaluated compounds exhibited antiviral activity against Herpes simplex virus type 1 (HSV‐1) KOS strain (TK+) and Field and B2006 strains (TK‐) in Vero cells.

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New metabolites of drospirenone obtained in Mucorales fungi culture

Cited by 6 publications

References 48 publications

Screening a Strain of Klebsiella sp. O852 and the Optimization of Fermentation Conditions for Trans-Dihydrocarvone Production

Screening a Strain of Klebsiella sp. O852 and the Optimization of Fermentation Conditions for Trans-Dihydrocarvone Production

Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

An Efficient Lipase‐Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir‐Resistant Strains

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