scholarly journals Chemo-Enzymatic Cascade for the Generation of Fragrance Aldehydes

Catalysts ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 932
Author(s):  
Daniel Schwendenwein ◽  
Anna K. Ressmann ◽  
Marcello Entner ◽  
Viktor Savic ◽  
Margit Winkler ◽  
...  
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives ◽  
Saccharomyces Pastorianus ◽  
Enzymatic Reduction ◽  
Target Molecules ◽  
Metal Catalyzed ◽  
High Throughput Assay

In this study, we present the synthesis of chiral fragrance aldehydes, which was tackled by a combination of chemo-catalysis and a multi-enzymatic in vivo cascade reaction and the development of a highly versatile high-throughput assay for the enzymatic reduction of carboxylic acids. We investigated a biocompatible metal-catalyzed synthesis for the preparation of α or β substituted cinnamic acid derivatives which were fed directly into the biocatalytic system. Subsequently, the target molecules were synthesized by an enzymatic cascade consisting of a carboxylate reduction, followed by the selective C-C double bond reduction catalyzed by appropriate enoate reductases. We investigated a biocompatible oxidative Heck protocol and combined it with cells expressing a carboxylic acid reductase from Neurospora crassa (NcCAR) and an ene reductase from Saccharomyces pastorianus for the production fragrance aldehydes.

scholarly journals Germinated and Ungerminated Seeds Extract from TwoLupinusSpecies: Biological Compounds Characterization and In Vitro and In Vivo Evaluations

2016 ◽  
Vol 2016 ◽  
pp. 1-8 ◽  
Author(s):  
Bogdan Andor ◽  
Corina Danciu ◽  
Ersilia Alexa ◽  
Istvan Zupko ◽  
Elena Hogea ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Therapeutic Potential ◽  
Lupinus Albus ◽  
Biological Evaluation ◽  
Lupinus Angustifolius ◽  
Cinnamic Acid Derivatives ◽  
Natural Agents ◽  
Germinated Seeds

In recent years, nutraceuticals attracted a great amount of attention in the biomedical research due to their significant contribution as natural agents for prevention of various health issues. Ethanolic extracts from the ungerminated and germinated seeds ofLupinus albusL. andLupinus angustifoliusL. were analyzed for the content in isoflavones (genistein) and cinnamic acid derivatives. Additionally, the extracts were evaluated for antimicrobial, antiproliferative, and anti-inflammatory properties, using in vitro and in vivo tests. Germination proved to be a method of choice in increasing the amount of genistein and cinnamic acid derivatives in bothLupinus albusL. andLupinus angustifolius L.seeds. Biological evaluation of all vegetal extracts revealed a weak therapeutic potential for both ungerminated and germinated seeds.

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

2021 ◽  
Author(s):  
Bin Zhao ◽  
Bo Xu
Keyword(s):  
Double Bond ◽  
Visible Light ◽  
Cinnamic Acid ◽  
Oxidative Cyclization ◽  
Coumarin Derivatives ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives ◽  
Double Bond Isomerization ◽  
Photocatalytic Synthesis

We have developed an efficient photocatalytic synthesis of coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids.

Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (88) ◽  
pp. 71942-71954 ◽  
Author(s):  
Mohammad Ali Zolfigol ◽  
Roya Ayazi-Nasrabadi ◽  
Saeed Baghery
Keyword(s):  
Carboxylic Acid ◽  
Cinnamic Acid ◽  
Sulfonic Acid ◽  
Solid Acids ◽  
Synthesis And Characterization ◽  
Nano Structure ◽  
Cinnamic Acid Derivatives ◽  
Catalytic Applications ◽  
Green Conditions

Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

Synthesis, Characterization and evaluation of Anti-inflammatory and Antimicrobial Properties of some Cinnamic Acid Derivatives

2020 ◽  
Vol 16 (1) ◽  
pp. 1-8
Author(s):  
B.B Jacob ◽  
H. Baba ◽  
J.O. Oluwadiya
Keyword(s):  
Dose Level ◽  
Cinnamic Acid ◽  
Condensation Reaction ◽  
Antimicrobial Activities ◽  
High Yield ◽  
Cinnamic Acid Derivatives ◽  
13C Nuclear Magnetic Resonance ◽  
Vis Spectroscopy ◽  
Anti Inflammatory

Background: Cinnamic acid and derivatives are widely spread in plants. They are important intermediates in the synthesis of many aromatic compounds and are known to have diverse biological activities.Objectives: To synthesize, characterize and evaluate some cinnamic acid derivatives, for possible antimicrobial and anti-inflammatory activities.Material and methods: Different cinnamic acid derivatives were synthesized by Knoevenagel condensation reaction between malonic acid and various derivatives of benzaldehydes in the presence of pyridine and hydrochloric acid. The cinnamic acid epoxide was formed in the presence of hydrogen peroxide and KOH, while dihydro-cinnamic acid and paramethoxy-dihydro-cinnamic acids were formed by reducing cinnamic acid and paramthoxy-cinnamic acid respectively with raney nickel in the presence of 10% KOH. The final products were purified on column chromatography (CC), eluting with petroleum spirit/ethyl acetate. All the synthesized compounds were unequivocally characterized using the combination of UV-Vis Spectroscopy, infra-red (FTIR), 1H and 13C Nuclear Magnetic Resonance (NMR) spectroscopy. In-vivo anti-inflammatory activities of the synthesized compounds was investigated using egg albumin-induced paw oedema in rat; while antimicrobial activity was evaluated by agar diffusion method.Results: The compounds were obtained in high yield (30 – 97 %) and purity. 3,4-dioxomethylene cinnamic acid produced the highest (60.8%) and significant (p < 0.05) anti-inflammatory effect at the 2nd hour of the highest dose. Dihydro-cinnamic acid and cinnamic acid epoxide with 4mg/kg dose produced 55.5% and 54.9% inhibition of inflammation respectively at the second hour, while para-methoxy-cinnamic acid at the second hour with 2 mg/kg dose level produced 54.0% inhibition. The reference compound; diclofenac produced no significant inhibition of inflammation at 4mg/kg dose level. All the compounds showed mild antimicrobial activities against the tested organisms.Conclusion: The findings from the study indicate that the synthesized compounds possess mild anti-inflammatory, with weak antibacterial and antifungal activities. Keywords: anti-inflammatory, antimicrobial, cinnamic acid derivatives, Knoevenagel

Combinatorial Synthesis of Novel 9R-Acyloxyquinine Derivatives as Insecticidal Agents

2020 ◽  
Vol 23 (2) ◽  
pp. 111-118
Author(s):  
Zhiping Che ◽  
Jinming Yang ◽  
Di Sun ◽  
Yuee Tian ◽  
Shengming Liu ◽  
...  
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Insecticidal Activity ◽  
Structural Modification ◽  
Combinatorial Synthesis ◽  
Hydroxyl Group ◽  
Botanical Insecticide ◽  
Mythimna Separata ◽  
Lead Compounds

Background: It is one of the effective ways for pesticide innovation to develop new insecticides from natural products as lead compounds. Quinine, the main alkaloid in the bark of cinchona tree as well as in plants in the same genus, is recognized as a safe and potent botanical insecticide to many insects. The structural modification of quinine into 9R-acyloxyquinine derivatives is a potential approach for the development of novel insecticides, which showed more toxicity than quinine. However, there are no reports on the insecticidal activity of 9Racyloxyquinine derivatives to control Mythimna separata. Methods: Endeavor to discover biorational natural products-based insecticides, 20 novel 9Racyloxyquinine derivatives were prepared and assessed for their insecticidal activity against M. separata in vivo by the leaf-dipping method at 1 mg/mL. Results: Among all the compounds, especially derivatives 5i, 5k and 5t exhibited the best insecticidal activity with final mortality rates of 50.0%, 57.1%, and 53.6%, respectively. Conclusion: Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9- substitution is well tolerated; modification of out-ring double-bond is acceptable, and hydrogenation of double-bond enhances insecticidal activity; Quinine ring is essential and open of it is not acceptable. These preliminary results will pave the way for further modification of quinine in the development of potential new insecticides.

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 &#181;M, 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.

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

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.

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