scholarly journals INHIBITORY POTENTIAL OF SOME SYNTHETIC CINNAMIC ACID DERIVATIVES TOWARDS TYROSINASE ENZYME

2010 ◽  
Vol 9 (1) ◽  
pp. 158-168
Author(s):  
Lanny Hartanti ◽  
Henry Kurnia Setiawan
Keyword(s):  
Cinnamic Acid ◽  
Enzymatic Reaction ◽  
Enzyme Reaction ◽  
Para Position ◽  
Inhibition Kinetics ◽  
Tyrosinase Inhibition ◽  
Cinnamic Acid Derivatives ◽  
Inhibition Effect ◽  
Tyrosinase Enzyme ◽  
Inhibitory Potential

Cinnamic acid is one of known tyrosinase inhibitors. This study investigated the inhibition of tyrosinase activity of some cinnamic acid derivatives, i.e. 4-buthoxy-cinnamic acid, 4-n-butylcinnamic acid and 4-phenylcinnamic acid. Each inhibitor used in this research had the same type of inhibition towards enzymatic activity, i.e. mixed type inhibition of competitive and non competitive type. The potential sequence of tyrosinase inhibition based on the ratio of its IC50 compared to cinnamic acid, from the lowest to the highest were 4-buthoxycinnamic acid, 4-phenylcinnamic acid and 4-n-butylcinnamic acid. Based on the obtained results of this research, it was disclosed that n-butyl substituent on para position did not increase the inhibition effect of cinnamic acid towards tyrosinase enzymatic reaction. But in the other hand, buthoxy and phenyl substituent on para position could increase the inhibition effect of cinnamic acid towards tyrosinase enzymatic reaction because buthoxy substituent increased the similarity of its structure with the substrate of enzymatic reaction while phenyl susbtituent blocked the substrate-enzyme reaction.   Keywords: tyrosinase; L-DOPA; inhibition kinetics; IC50, cinnamic acid

Novel Piperazine Amides of Cinnamic Acid Derivatives as Tyrosinase Inhibitors

2018 ◽  
Vol 16 (1) ◽  
pp. 36-44 ◽  
Author(s):  
Zehra Tuğçe Gür ◽  
Fatma Sezer Şenol ◽  
Suhaib Shekfeh ◽  
İlkay Erdoğan Orhan ◽  
Erden Banoğlu ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Active Site ◽  
Agaricus Bisporus ◽  
Biological Activities ◽  
Docking Simulation ◽  
Cinnamic Acid Derivatives ◽  
In Silico Docking ◽  
Amide Derivatives ◽  
Tyrosinase Inhibitors ◽  
Further Development

Background: A series of novel cinnamic acid piperazine amide derivatives has been designed and synthesized, and their biological activities were also evaluated as potential tyrosinase inhibitors. Methods: Compounds 9, 11 and 17 showed the most potent biological activity (IC50 = 66.5, 61.1 and 66 µM, respectively). In silico docking simulation was performed to position compound 11 into the Agaricus bisporus mushroom tyrosinase’s active site to determine the putative binding interactions. Results and Conclusion: The results indicated that compound 11 could serve as a promising lead compound for further development of potent tyrosinase inhibitors.

Evaluation of Antinociceptive and Anti-Inflammatory Activities of a New Triterpene Saponin from Bauhinia variegata Leaves

2009 ◽  
Vol 64 (11-12) ◽  
pp. 798-808 ◽  
Author(s):  
Mona A. Mohamed ◽  
Madeha R. Mammoud ◽  
Heiko Hayen
Keyword(s):  
High Resolution ◽  
Spectral Data ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives ◽  
Triterpene Saponin ◽  
H Nmr ◽  
Antischistosomal Activity ◽  
Bauhinia Variegata ◽  
Anti Inflammatory ◽  
C Nmr

A new triterpene saponin, named as 23-hydroxy-3α-[O-α-L-1C4-rhamnopyranosyl-(1´´4´)- O-α-L-4C1-arabinopyranosyl-oxy]olean-12-en-28-oic acid O-α-L-1C4-rhamnopyranosyl- (1´´´´´→4´´´´)-O-β-D-4C1-glucopyranosyl-(1´´´´→6´´´)-O-β-D-4C1-glucopyranosyl ester (9), was isolated from the leaves of Bauhinia variegata Linn. In addition, six flavonoid compounds along with two cinnamic acid derivatives were isolated and identified based on their chromatographic properties, and chemical and spectral data (ESI-high resolution-MSn, 1H NMR, 13C NMR, 1H-1H COSY, HSQC, and HMBC). Compound 9 was found to be nontoxic (LD50) and to have significant anti-inflammatory and antinociceptive activities. It also showed a slight antischistosomal activity.

On the interpretation of tyrosinase inhibition kinetics

2013 ◽  
Vol 29 (1) ◽  
pp. 92-99 ◽  
Author(s):  
Wei Sun ◽  
Michael Wendt ◽  
Gerhard Klebe ◽  
Klaus-Heinrich Röhm
Keyword(s):  
Inhibition Kinetics ◽  
Tyrosinase Inhibition

Cinnamic Acid Derivatives as Anticancer Agents-A Review

2011 ◽  
Vol 18 (11) ◽  
pp. 1672-1703 ◽  
Author(s):  
P. De ◽  
M. Baltas ◽  
F. Bedos-Belval
Keyword(s):  
Cinnamic Acid ◽  
Anticancer Agents ◽  
Cinnamic Acid Derivatives

Asymmetric epoxidation of cinnamic acid derivatives using dioxiranes generated in situ from dehydrocholic acid

2001 ◽  
Vol 12 (8) ◽  
pp. 1113-1115 ◽  
Author(s):  
Olga Bortolini ◽  
Marco Fogagnolo ◽  
Giancarlo Fantin ◽  
Silvia Maietti ◽  
Alessandro Medici
Keyword(s):  
Cinnamic Acid ◽  
Asymmetric Epoxidation ◽  
Cinnamic Acid Derivatives ◽  
Dehydrocholic Acid

scholarly journals The reactivity of cinnamic acid derivatives as lignin precursors

2020 ◽  
Vol 15 (4) ◽  
pp. 7-13
Author(s):  
O. K. Karimov ◽  
G. Y. Kolchina ◽  
G. A. Teptereva ◽  
I. A. Chetvertneva ◽  
E. K. Karimov ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Cinnamic Acid ◽  
Density Functional ◽  
Density Functional Method ◽  
Hydroxycinnamic Acids ◽  
Geometric Parameters ◽  
Hydroxyl Group ◽  
Chemical Calculation ◽  
Cinnamic Acid Derivatives ◽  
Oxygen Atoms

Objectives. Cinnamic acid derivatives belong to a large class of phenolic compounds, which are widely distributed in plants and have high potential for use in the medical and industrial fields. They have various useful practical properties, e.g., antioxidant, anti-inflammatory, antiplatelet, and anti-melanogenic properties. Hydroxycinnamic acids are of particular interest as phenylpropanoids, which are the starting compounds of lignin. The aim of this work was to study the electronic structure and analyze the reactivity of the simplest representatives of phenylpropanoids formed during the biosynthesis of the coumaric (p-hydroxycinnamic), caffeic (3,4-dihydroxycinnamic), ferulic (3-methoxy-4-hydroxycinnamic), sinapic (3,5-dimethoxy-4- hydroxycinnamic), and 3,4-dimethoxycinnamic acids. These acids are the biogenetic precursors of most other phenolic compounds (coumarins, melanins, lignins, and flavonoids) and are found in almost all higher plants.Methods. Calculations with full optimization of the geometric parameters were performed using the original Hartree–Fock theory and hybrid density functional method. All calculations were performed using the Firefly program. Results. A comparative quantum chemical calculation of the geometric parameters of hydroxycinnamic acid molecules was conducted via two methods, and the values of the charges on atoms according to Mulliken were determined. It was found that with the addition of hydroxyl and methoxy substituents at the meta and para positions relative to the carboxyl fragment, the electron density shifts toward the benzene ring, and the symmetry of the molecule decreases. Additionally, in these structures, there is π,π-conjugation of the carboxyl fragment of the –СН=СНСООН molecule with the aromatic ring, which significantly affects the geometric configuration of the molecule. The maximum positive charge is concentrated on the C9 atom, while the maximum negative charge is on the oxygen atoms belonging to the methoxy substituents and the hydroxyl group, which confirms the role of oxygen atoms in the chemical transformations of acids. Conclusions. Two different methods were used to calculate the geometric, electronic, and energy parameters and electrophilicity indices of the studied hydroxycinnamic acids in the gas phase. The obtained values were consistent (within the limits of error) with the experimental data as well as the results described in earlier works’ calculations by other methods.

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