Combinatorial Synthesis of Novel 1-Sulfonyloxy/acyloxyeugenol Derivatives as Fungicidal Agents

2021 ◽  
Vol 24 ◽  
Author(s):  
Genqiang Chen ◽  
Lina Zhu ◽  
Jiaxuan He ◽  
Song Zhang ◽  
Yuanhao Li ◽  
...  
Keyword(s):  
Fungicidal Activity ◽  
High Efficiency ◽  
Biological Activities ◽  
Phytophthora Capsici ◽  
Effective Control ◽  
Syzygium Aromaticum ◽  
Wide Range ◽  
Structural Skeleton ◽  
Acyloxy Group

Background: Developing the high-efficiency and low-risk small-molecule green-fungicide is the key to effective control of the plant pathogenic oomycetes. Essential oils play a very important role in novel fungicide discovery for their unique sources and potential target sites. Eugenol, a kind of plant essential oil, was mainly isolated from the unopened and dried flower buds of Syzygium aromaticum of the Myrtaceae family. Due to its unique structural skeleton, eugenol and its derivatives have exhibited a wide range of biological activities. However, study on the synthesis of novel 1-sulfonyloxy/acyloxyeugenol derivatives as fungicidal agents against Phytophthora capsici has not yet been reported. Methods: Twenty-six novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) were prepared and their structures were well characterized by 1H NMR, HRMS, and m.p.. Their fungicidal activity was evaluated against P. capsici by using the mycelial growth rate method. Results: To find novel natural-product-based fungicidal agents to control the plant pathogenic oomycetes, we herein designed and synthesized two series of novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) as fungicidal agents against P. capsici Leonian, in vitro. Results of fungicidal activity revealed that, among all compounds, especially compounds 3a, 3f, and 3n displayed the most potent anti-oomycete activity against P. capsici with EC50 values of 79.05, 75.05, and 70.80, respectively. Conclusion: The results revealed that the anti-oomycete activity of eugenol with the sulfonyloxy group was higher than that with the acyloxy group. It is suggested that the fungicidal activity of eugenol can be improved by introducing the sulfonyloxy group. This will pave the way for further design, structural modification, and to develop eugenol derivatives as fungicidal agents.

Combinatorial Synthesis of Novel 3/5(3,5)-(Di)nitro/chloropaeonol Carbonyl Hydrazone Derivatives as Nematicidal Agents

2021 ◽  
Vol 24 ◽  
Author(s):  
Genqiang Chen ◽  
Lina Zhu ◽  
Yanfei Xia ◽  
Jinming Yang ◽  
Song Zhang ◽  
...  
Keyword(s):  
High Efficiency ◽  
Biological Activities ◽  
Science Research ◽  
Nematicidal Activity ◽  
Effective Control ◽  
Root Bark ◽  
Naturally Occurring ◽  
Whole Plant ◽  
Wide Range

Background: Developing the high-efficiency and low-risk small-molecule green-nematocide is the key of effective control of the nematodes. Paeonol, is a naturally occurring phenolic compound, isolated from the root bark of Paeonia suffruticosa and the whole plant of Cynanchum paniculatum. Due to its crucial phenolic ketone skeleton, modern biological science research has indicated that paeonol has a wide range of biological activities. The structural modification of paeonol into paeonol carbonyl hydrazone derivatives is a potential approach for the development of novel nematodes, which showed more toxicity than paeonol. However, there are no reports on the nematicidal activity of paeonol carbonyl hydrazone derivatives to control Heterodera glycines. Results: We always endeavor to discover and develop biorational natural products-based pesticidal agents, 4 significant intermediates and 21 novel 3/5(3,5)-(di)nitro/chloropaeonol carbonyl hydrazone derivatives were prepared, and their structures well characterized by 1H NMR, HRMS, MS, and mp. Due to the steric hindrance, the substituents on the C=N double bond of all hydrazine compounds adopted E configuration. Results of nematicidal activity revealed that, among all compounds, especially 5-nitropaeonol (5) and 3,5-dinitropaeonol (7) displayed the most potent nematicidal activity H. glycines in vivo with LC50 values of 0.0323 and 0.0367 mg/mL, respectively. Conclusion: It suggested that for the 3/5(3,5)-(di)nitro/chloropaeonol carbonyl hydrazone derivatives, a nitro group introduced at C5 position of 1 was necessary for obtaining the potent compound as nematicidal agents. These preliminary results will pave the way for further modification of paeonol in the development of potential new nematicides.

Chalcones: As potent α-amylase enzyme inhibitors; synthesis, in vitro, and in silico studies

2020 ◽  
Vol 16 ◽  
Author(s):  
Mahboob Ali ◽  
Momin Khan ◽  
Khair Zaman ◽  
Abdul Wadood ◽  
Maryam Iqbal ◽  
...  
Keyword(s):  
In Silico ◽  
Enzyme Inhibitors ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Type Ii Diabetes Mellitus ◽  
Spectroscopic Techniques ◽  
Chalcone Derivatives ◽  
In Silico Studies ◽  
Wide Range

: Background: The inhibition of α-amylase enzyme is one of the best therapeutic approach for the management of type II diabetes mellitus. Chalcone possesses a wide range of biological activities. Objective: In the current study chalcone derivatives (1-17) were synthesized and evaluated their inhibitory potential against α-amylase enzyme. Method: For that purpose, a library of substituted (E)-1-(naphthalene-2-yl)-3-phenylprop-2-en-1-ones was synthesized by ClaisenSchmidt condensation reaction of 2-acetonaphthanone and substituted aryl benzaldehyde in the presence of base and characterized via different spectroscopic techniques such as EI-MS, HREI-MS, 1H-, and 13C-NMR. Results: Sixteen synthetic chalcones were evaluated for in vitro porcine pancreatic α-amylase inhibition. All the chalcones demonstrated good inhibitory activities in the range of IC50 = 1.25 ± 1.05 to 2.40 ± 0.09 μM as compared to the standard commercial drug acarbose (IC50 = 1.34 ± 0.3 μM). Conclusion: Chalcone derivatives (1-17) were synthesized, characterized, and evaluated for their α-amylase inhibition. SAR revealed that electron donating groups in the phenyl ring have more influence on enzyme inhibition. However, to insight the participation of different substituents in the chalcones on the binding interactions with the α-amylase enzyme, in silico (computer simulation) molecular modeling analyses were carried out.

Associated microflora of medicinal ferns: biotechnological potentials and possible applications

2016 ◽  
Vol 5 (03) ◽  
pp. 4927 ◽  
Author(s):  
Shubhi Srivastava ◽  
Paul A. K.
Keyword(s):  
Secondary Metabolites ◽  
Growth Promotion ◽  
Biological Activities ◽  
Hydrolytic Enzymes ◽  
In Vitro Production ◽  
Wide Range ◽  
Negative Effect ◽  
Bacteria And Fungi

Plant associated microorganisms that colonize the upper and internal tissues of roots, stems, leaves and flowers of healthy plants without causing any visible harmful or negative effect on their host. Diversity of microbes have been extensively studied in a wide variety of vascular plants and shown to promote plant establishment, growth and development and impart resistance against pathogenic infections. Ferns and their associated microbes have also attracted the attention of the scientific communities as sources of novel bioactive secondary metabolites. The ferns and fern alleles, which are well adapted to diverse environmental conditions, produce various secondary metabolites such as flavonoids, steroids, alkaloids, phenols, triterpenoid compounds, variety of amino acids and fatty acids along with some unique metabolites as adaptive features and are traditionally used for human health and medicine. In this review attention has been focused to prepare a comprehensive account of ethnomedicinal properties of some common ferns and fern alleles. Association of bacteria and fungi in the rhizosphere, phyllosphere and endosphere of these medicinally important ferns and their interaction with the host plant has been emphasized keeping in view their possible biotechnological potentials and applications. The processes of host-microbe interaction leading to establishment and colonization of endophytes are less-well characterized in comparison to rhizospheric and phyllospheric microflora. However, the endophytes are possessing same characteristics as rhizospheric and phyllospheric to stimulate the in vivo synthesis as well as in vitro production of secondary metabolites with a wide range of biological activities such as plant growth promotion by production of phytohormones, siderophores, fixation of nitrogen, and phosphate solubilization. Synthesis of pharmaceutically important products such as anticancer compounds, antioxidants, antimicrobials, antiviral substances and hydrolytic enzymes could be some of the promising areas of research and commercial exploitation.

scholarly journals In vitro antimicrobial activity of the organic extract of Cladonia substellata Vainio and usnic acid against Staphylococcus spp. obtained from cats and dogs

2017 ◽  
Vol 37 (4) ◽  
pp. 368-378 ◽  
Author(s):  
Jusciêne B. Moura ◽  
Agueda C. de Vargas ◽  
Gisele V. Gouveia ◽  
João J. de S. Gouveia ◽  
Juracy C. Ramos-Júnior ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Biological Activities ◽  
Meca Gene ◽  
Usnic Acid ◽  
Organic Extract ◽  
In Vitro Antimicrobial Activity ◽  
Low Concentrations ◽  
Wide Range ◽  
Staphylococcus Spp

ABSTRACT: Cladonia substellata Vainio is a lichen found in different regions of the world, including the Northeast of Brazil. It contains several secondary metabolites with biological activity, including usnic acid, which has exhibited a wide range of biological activities. The aim of this study was to evaluate the in vitro antimicrobial activity of the organic extract of C. substellata and purified usnic acid. Initially, Staphylococcus spp., derived from samples of skin and ears of dogs and cats with suspected pyoderma and otitis, were isolated and analyzed. In antimicrobial susceptibility testing against Staphylococcus spp., 77% (105/136) of the isolates were resistant to the antimicrobials tested. In the assessment of biofilm production, 83% (113/136) were classified as producing biofilm. In genetic characterization, 32% (44/136) were positive for blaZ, no isolate (0/136) was positive for the mecA gene, and 2% (3/136) were positive for the icaD gene. The in vitro antimicrobial activity of the organic extract of C. substellata and purified usnic acid against Staphylococcus spp. ranged from 0.25mg/mL to 0.0019mg/mL, inhibiting bacterial growth at low concentrations. The substances were more effective against biofilm-producing bacteria (0.65mg/mL-0.42mg/mL) when compared to non-biofilm producing bacteria (2.52mg/mL-2.71mg/mL). Usnic acid and the organic extract of C. substellata can be effective in the treatment of pyoderma and otitis in dogs and cats caused by Staphylococcus spp.

scholarly journals Enhanced Recovery of Antioxidant Compounds from Hazelnut (Corylus avellana L.) Involucre Based on Extraction Optimization: Phytochemical Profile and Biological Activities

Antioxidants ◽  
2019 ◽  
Vol 8 (10) ◽  
pp. 460 ◽  
Author(s):  
Rusu ◽  
Fizeșan ◽  
Pop ◽  
Gheldiu ◽  
Mocan ◽  
...  
Keyword(s):  
Bioactive Compounds ◽  
Enhanced Recovery ◽  
Biological Activities ◽  
Natural Antioxidants ◽  
Antioxidant Compounds ◽  
Cancerous Cell ◽  
Wide Range ◽  
Quantitative Analyses ◽  
Corylus Avellana L

Tree nut by-products could contain a wide range of phytochemicals, natural antioxidants, which might be used as a natural source for dietary supplements. The aim of the present study was to evaluate the phenolic and sterolic composition, as well as the antioxidant and other biological activities, of hazelnut involucre (HI) extracts. Experimental designs were developed in order to select the optimum extraction conditions (solvent, temperature, time) using turbo-extraction by Ultra-Turrax for obtaining extracts rich in bioactive compounds. Qualitative and quantitative analyses were performed by LC-MS and LC-MS/MS and they revealed important amounts of individual polyphenols and phytosterols, molecules with antioxidant potential. The richest polyphenolic HI extract with the highest antioxidant activity by TEAC assay was further evaluated by other in vitro antioxidant tests (DPPH, FRAP) and enzyme inhibitory assays. Additionally, the cytotoxic and antioxidant effects of this extract on two cancerous cell lines and on normal cells were tested. This is the first study to analyze the composition of both hydrophilic and lipophilic bioactive compounds in HI extracts. Our findings reveal that this plant by-product presents strong biological activities, justifying further research, and it could be considered an inexpensive source of natural antioxidants for food, pharmaceutical, or cosmetic industry.

scholarly journals Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

Biomolecules ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 241 ◽  
Author(s):  
Walter Ferreira da Silva Júnior ◽  
Danielle Lima Bezerra de Menezes ◽  
Luana Carvalho de Oliveira ◽  
Letícia Scherer Koester ◽  
Patrícia Danielle Oliveira de Almeida ◽  
...  
Keyword(s):  
Inclusion Complexes ◽  
Biological Activities ◽  
Physicochemical Characterization ◽  
Inflammatory Activity ◽  
Scanning Calorimetry ◽  
Promising Alternative ◽  
Wide Range ◽  
Natural Mixture ◽  
Anti Inflammatory

α, β amyrin (ABAM) is a natural mixture of pentacyclic triterpenes that has a wide range of biological activities. ABAM is isolated from the species of the Burseraceae family, in which the species Protium is commonly found in the Amazon region of Brazil. The aim of this work was to develop inclusion complexes (ICs) of ABAM and β-cyclodextrin (βCD) and hydroxypropyl-β-cyclodextrin (HPβCD) by physical mixing (PM) and kneading (KN) methods. Interactions between ABAM and the CD’s as well as the formation of ICs were confirmed by physicochemical characterization in the solid state by Fourier transform infrared (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), thermogravimetry (TG) and differential scanning calorimetry (DSC). Physicochemical characterization indicated the formation of ICs with both βCD and HPβCD. Such ICs were able to induce changes in the physicochemical properties of ABAM. In addition, the formation of ICs with cyclodextrins showed to be an effective and promising alternative to enhance the anti-inflammatory activity and safety of ABAM.

scholarly journals IN VITRO CALLUS INDUCTION AND COMPARATIVE GC-MS ANALYSIS OF METHANOLIC EXTRACTS OF CALLUS AND LEAF SAMPLES OF AMPELOCISSUS LATIFOLIA (ROXB.) PLANCH

2018 ◽  
Vol 10 (9) ◽  
pp. 68
Author(s):  
Deep Chhavi Anand ◽  
Rishikesh Meena ◽  
Vidya Patni
Keyword(s):  
Callus Induction ◽  
Culture Media ◽  
Biological Activities ◽  
Gas Chromatography Mass Spectrometry ◽  
Dodecanoic Acid ◽  
Stem Explants ◽  
Ms Analysis ◽  
Wide Range

Objective: The aim of the present study was to develop a callus induction protocol and comparative study of therapeutic phytochemicals present in in vivo leaf and in vitro callus extracts through Gas Chromatography-Mass Spectrometry analysis.Methods: Murashige and Skoog media was used as culture media for callus induction. In vitro callus induction protocol was developed by studying the effects of various plant growth regulators like auxin, 2, 4-D (2,4-dichlorophenoxyacetic acid), NAA (naphthalic acetic acid), alone and in combination with cytokinin BAP (benzyl aminopurine), on leaf and stem explants. The GC-MS analysis of Ampelocissus latifolia was carried out on Shimadzu QP-2010 plus with thermal desorption system TD 20 to study the phytochemical profile.Results: In vitro callus induction protocol was developed for the plant and callusing was done from leaf and stem explants of Ampelocissus latifolia. The best result for callus induction was obtained using leaf explant, and callus production were maximum in Murashige and Skoog medium fortified with BAP (0.5 mg/l) and NAA (1.0 mg/l). Major compounds identified in the GC-MS analysis were Campesterol, Stigmasterol, Beta-Sitosterol, Docosanol, Dodecanoic acid, etc., in in vitro extract and Beta Sitosterol, Tocopherol, Squalene, Bergamot oil, Margarinic acid, Hexadecanoic acid, etc., in in vivo extract. The different active phytochemicals identified have been found to possess a wide range of biological activities, thus this analysis forms a basis for the biological characterization and importance of the compounds identified for human benefits.Conclusion: This is the first report on callus induction in Ampelocissus latifolia. From the results obtained through the in vitro callus induction and its comparative GCMS analysis with in vivo extract, it is revealed that Ampelocissus latifolia contains various bioactive compounds that are of importance for phytopharmaceutical uses. The GCMS analysis revealed that the amount of Beta-sitosterol and 5-Hydroxymethylfurfural (HMF) was very high in in vitro extract as compared to in vivo extract.

Preparation, Characterization, and In Vitro Evaluation of Resveratrol-Loaded Bovine Serum Album Nanoparticles

2011 ◽  
Vol 345 ◽  
pp. 349-354 ◽  
Author(s):  
Jia Lei Li ◽  
Yuan Gang Zu ◽  
Xiu Hua Zhao ◽  
Dong Mei Zhao ◽  
Xiao Qiang Chen ◽  
...  
Keyword(s):  
Bovine Serum ◽  
Biological Activities ◽  
Cardiovascular Effects ◽  
Entrapment Efficiency ◽  
Cross Linking ◽  
Nano Technology ◽  
Beneficial Effects ◽  
Wide Range

Resveratrol (RES) is a naturally occurring triphenolic phytoalexin compound exerting numerous beneficial effects in the organism. It has a wide range of biological activities in vitro as well as in vivo, such as anti-cancer, antioxidant, anti-inflammatory and beneficial cardiovascular effects. But, its low solubility in water led to its poor absorption in vivo and low bioavailability. Bovine serum album (BSA) nanoparticles have emerged as versatile desired carrier systems due to its ready availability, biodegradability, lack of toxicity and immunogenicity with fast development of nano technology. In this study, RES-BSANPS were prepared by a desolvation method and chemical cross-linking with glutaraldehyde successfully. Results controlled conditions (concentration of BSA, 10 mg/ml; pH = 9.0; volume of ethanol, 6 ml; volume of 0.25 % glutaraldehyde, 100 µl; amount of RES, 6.7 mg; cross-linking time, 24 h at room temperature (1 ml/min)) for entrapment efficiency, loading efficiency, mean particle size and zeta potential, were found to be 88.7 %, 39.4 %, 175.4 ± 0.5 nm, -35.93 ± 0.79 mV, respectively.

scholarly journals Exploitation of Cytotoxicity of Some Essential Oils for Translation in Cancer Therapy

2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Rossella Russo ◽  
Maria Tiziana Corasaniti ◽  
Giacinto Bagetta ◽  
Luigi Antonio Morrone
Keyword(s):  
Multidrug Resistance ◽  
Essential Oils ◽  
Biological Activities ◽  
Complex Mixtures ◽  
Antitumor Drugs ◽  
Wide Range ◽  
Growing Body ◽  
Anticancer Treatment

Essential oils are complex mixtures of several components endowed with a wide range of biological activities, including antiseptic, anti-inflammatory, spasmolytic, sedative, analgesic, and anesthetic properties. A growing body of scientific reports has recently focused on the potential of essential oils as anticancer treatment in the attempt to overcome the development of multidrug resistance and important side effects associated with the antitumor drugs currently used. In this review we discuss the literature on the effects of essential oils in  in vitroandin vivomodels of cancer, focusing on the studies performed with the whole phytocomplex rather than single constituents.

The molecular biology of mammalian arachidonic acid metabolism

1991 ◽  
Vol 260 (2) ◽  
pp. L13-L28 ◽  
Author(s):  
E. Sigal
Keyword(s):  
Arachidonic Acid ◽  
Acid Metabolism ◽  
Recombinant Dna ◽  
Biological Activities ◽  
Biological Effects ◽  
Arachidonic Acid Metabolism ◽  
Bioactive Metabolites ◽  
Wide Range

The metabolism of arachidonic acid by cyclooxygenase and lipoxygenase enzymes results in a wide range of oxidized products with potent biological activities. These metabolites, which include the prostaglandins and leukotrienes, have been implicated in the pathogenesis of a variety of inflammatory diseases. Research over the last decade has focused primarily on the elucidation of the chemical structure of the metabolites and their biological effects in vitro and in vivo. Recently, research on the enzymes that produce these bioactive metabolites through oxidization of arachidonic acid has intensified. Recombinant DNA techniques have enabled investigators to determine the nucleotide sequences for several of the enzymes in the arachidonic acid cascade. The resulting cDNAs are now being used to further investigate the biochemical and biological features of arachidonic acid metabolism. The purpose of this paper is to review how the cDNAs for these enzymes were obtained, what information they convey, and how they are being applied in current research.

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