scholarly journals Microbial Synthesis and Evaluation of Fungistatic Activity of 3-Butyl-3-hydroxyphthalide, the Mammalian Metabolite of 3-n-Butylidenephthalide

2021 ◽  
Vol 22 (14) ◽  
pp. 7600
Author(s):  
Joanna Gach ◽  
Teresa Olejniczak ◽  
Piotr Krężel ◽  
Filip Boratyński
Keyword(s):  
High Performance ◽  
Product Yield ◽  
Product Formation ◽  
Reversed Phase ◽  
Log P ◽  
P Value ◽  
Fungistatic Activity ◽  
Microdilution Method ◽  
Aspergillus Candidus ◽  
Layer Chromatography

Phthalides are bioactive compounds that naturally occur in the family Apiaceae. Considering their potentially versatile applications, it is desirable to determine their physical properties, activity and metabolic pathways. This study aimed to examine the utility of whole-cell biocatalysts for obtaining 3-butyl-3-hydroxyphthalide, which is the metabolite formulated during mammalian metabolism of 3-n-butylidenephthalide. We performed transformations using 10 strains of fungi, five of which efficiently produced 3-butyl-3-hydroxyphthalide. The product yield, determined by high-performance liquid chromatography, reached 97.6% when Aspergillus candidus AM 386 was used as the biocatalyst. Increasing the scale of the process resulted in isolation yields of 29–45% after purification via reversed-phase thin layer chromatography, depending on the strain of the microorganism used. We proposed different mechanisms for product formation; however, hydration of 3-n-butylidenephthalide seems to be the most probable. Additionally, all phthalides were tested against clinical strains of Candida albicans using the microdilution method. Two phthalides showed a minimum inhibitory concentration, required to inhibit the growth of 50% of organisms, below 50 µg/mL. The 3-n-butylidenephthalide metabolite was generally inactive, and this feature in combination with its low lipophilicity suggests its involvement in the detoxification pathway. The log P value of tested compounds was in the range of 2.09–3.38.

Hydrophobicity parameters (Log P) of glycoconjugated porphyrins for photodynamic therapy evaluated by reversed phase HPLC

2004 ◽  
Vol 08 (11) ◽  
pp. 1289-1292 ◽  
Author(s):  
Shiho Hirohara ◽  
Makoto Obata ◽  
Shun-ichiro Ogura ◽  
Ichiro Okura ◽  
Suguru Higashida ◽  
...  
Keyword(s):  
High Performance Liquid Chromatography ◽  
Photodynamic Therapy ◽  
High Performance ◽  
Reversed Phase ◽  
Log P ◽  
P Value ◽  
Reversed Phase Hplc ◽  
Free Base ◽  
P Values ◽  
Rp Hplc

Photodynamic therapy (PDT) is one of the most effective treatments for cancer. We synthesized and characterized a series of 16 glycoconjugated porphyrins using a modification of the Lindsey method in the presence of Zn ( OAc )2·2 H 2 O as a template. The Zn 2+ ion template strategy improved the yield about 3-fold in the case of meta-substituted tetraphenylporphyrins, and free-base porphyrins were obtaind almost quantitatively by demetalation with 4 M HCl . The hydrophobicity parameter (Log P) of these porphyrins was evaluated by reversed phase high-performance liquid chromatography (RP-HPLC). The Log P values ranged from +4.8 to +7.8, so that most of the compounds are amphiphilic. The effect of the glycopyranosyl unit on the hydrophobicity of these compounds is discussed on the basis of the Log P value.

scholarly journals Reversed-phase thin-layer chromatography behavior of aldopentose derivatives

2012 ◽  
Vol 66 (3) ◽  
pp. 365-372 ◽  
Author(s):  
Dragana Livaja-Popovic ◽  
Eva Loncar ◽  
Lidija Jevric ◽  
Radomir Malbasa
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Stationary Phases ◽  
Reversed Phase ◽  
Chromatographic Behavior ◽  
Log P ◽  
Retention Factors ◽  
Mobile Phases ◽  
Acetone Water ◽  
Layer Chromatography

Quantitative structure-retention relationships (QSRR) have been used to study the chromatographic behavior of some aldopentose. The behavior of aldopentose derivatives was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on the silica gel impregnated with paraffin oil stationary phases. Binary mixtures of methanol-water, acetone-water and dioxane-water were used as mobile phases. Retention factors, RM0, corresponding to zero percent organic modifier in the aqueous mobile phase was determined. Lipophilicity C0 was calculated as the ratio of the intercept and slope values. There was satisfactory correlation between them and log P values calculated using different theoretical procedures. Some of these correlations offer very good predicting models, which are important for a better understanding of the relationships between chemical structure and retention. The study showed that the hydrophobic parameters RM0 and C0 can be used as a measures of lipophilicity of investigated compounds.

scholarly journals Preparation and Hydro-Lipophilic Properties of Selected Novel Chlorinated and Brominated N-Arylcinnamamides

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 11
Author(s):  
Tomas Strharsky ◽  
Timotej Jankech ◽  
Jiri Kos ◽  
Kristina Maricakova ◽  
Andrea Pramukova ◽  
...  
Keyword(s):  
High Performance ◽  
Chemical Structure ◽  
Antimicrobial Agents ◽  
Reversed Phase ◽  
Log P ◽  
Organic Modifier ◽  
Chromatography Method ◽  
P Values ◽  
Liquid Chromatography Method ◽  
Derivatives Of

A series of six di- and tri-halogenated N-arylcinnamanilides designed as anti-inflammatory and antimicrobial agents was prepared and characterized. Since it is known that lipophilicity significantly influences the biological activity of compounds, the hydro-lipophilic properties of these di- and tri-substituted N-arylcinnamanilides were investigated in the study. All the discussed derivatives of cinnamic acid were analyzed using the reversed-phase high performance liquid chromatography method to measure lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, the correlations between the logarithm of the capacity factor k and log P/Clog P values calculated in various ways as well as the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed.

Preparative reversed-phase high-performance thin-layer chromatography for analysis of anthocyanins

2006 ◽  
Vol 19 (112) ◽  
pp. 463-466 ◽  
Author(s):  
Agnieszka Skalska ◽  
Anna Matysik ◽  
Marek Gerkowicz ◽  
Magdalena Wójciak-Kosior
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
High Performance ◽  
Reversed Phase ◽  
Layer Chromatography

scholarly journals Separation of 9-Fluorenylmethyloxycarbonyl Amino Acid Derivatives in Micellar Systems of High-Performance Thin-Layer Chromatography and Pressurized Planar Electrochromatography

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Beata Polak ◽  
Adam Traczuk ◽  
Sylwia Misztal
Keyword(s):  
Amino Acid ◽  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Mobile Phase ◽  
High Performance ◽  
Reversed Phase ◽  
Amino Acid Derivatives ◽  
Solute Retention ◽  
Micellar Systems ◽  
Layer Chromatography

AbstractThe problems with separation of amino acid mixtures in reversed-phase mode are the result of their hydrophilic nature. The derivatisation of the amino group of mentioned above solutes leads to their solution. For this purpose, 9-fluorenylmethoxycarbonyl chloroformate (f-moc-Cl) as the derivatisation reagent is often used. In our study, the separation of some f-moc- amino acid derivatives (alanine, phenylalanine, leucine, methionine, proline and tryptophan) with the use of micellar systems of reversed-phase high-performance thin-layer chromatography (HPTLC) and pressurized planar electrochromatography (PPEC) is investigated. The effect of surfactant concentration, its type (anionic, cationic and non-ionic) and mobile phase buffer pH on the discussed above solute migration distances are presented. Our work reveals that the increase of sodium dodecylsulphate concentration in the mobile phase has a different effect on solute retention in HPTLC and PPEC. Moreover, it also affects the order of solutes in both techniques. In PPEC, in contrast to the HPTLC technique, the mobile phase pH affects solute retention. The type of surfactant in the mobile phase also impacts solute retention and migration distances. A mobile phase containing SDS improves system efficiency in both techniques. Herein, such an effect is presented for the first time.

scholarly journals Preparation and Hydro-Lipophilic Properties of Methoxylated and Methylated 1-Hydroxynaphthalene-2-Carboxanilides

Proceedings ◽  
2018 ◽  
Vol 9 (1) ◽  
pp. 43 ◽  
Author(s):  
Iva Kapustikova ◽  
Tomas Gonec ◽  
Jiri Kos ◽  
Ewelina Spaczynska ◽  
Michal Oravec ◽  
...  
Keyword(s):  
Mobile Phase ◽  
High Performance ◽  
Chemical Structure ◽  
Reversed Phase ◽  
Log P ◽  
Organic Modifier ◽  
Chromatography Method ◽  
P Values ◽  
Liquid Chromatography Method ◽  
Substituted 1

A series of variously methoxylated and methylated N-aryl-1-hydroxynaphthalene-2-carboxanilides was prepared and characterized as potential anti-invasive agents. As it is known that lipophilicity significantly influences the biological activity of compounds, the hydro-lipophilic properties of these mono-, di- and tri-substituted 1-hydroxynaphthalene-2-carboxanilides are investigated in the study. All the discussed hydroxynaphthalene derivatives were analyzed using the reversed-phase, high-performance liquid chromatography method, to measure lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase, using an end-capped, non-polar C18 stationary reversed-phase column. The present study discusses the correlations between the logarithm of the capacity factor k and log P/Clog P values, calculated in various ways, as well as the relationships between the lipophilicity and the chemical structure of the studied compounds.

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