Synthesis of hybrid polyphenol/hydroxyapatite nanomaterials: adsorption vs. in situ incorporation

Plant-derived natural bioactive molecules are of great therapeutic potential but their application in nanomedicine has been so far scarcely studied. This work aimed at comparing two methodologies, i.e. adsorption and in situ incorporation, to prepare hybrid polyphenol/hydroxyapatite nanoparticles. Two flavonoids, baicalin and its aglycone derivative baicalein, and two phenolic acids derived from caffeic acid, rosmarinic and chlorogenic acids, were studied. Adsorption of these polyphenols on pre-formed hydroxyapatite nanoparticles did not modify particles size or shape and loading was less than 10 % (w/w). In contrast, presence of polyphenols during the synthesis of nanoparticles significantly impacted, and sometimes fully inhibited, hydroxyapatite formation, but recovered particles could exhibit higher loadings. Antioxidant properties of the polyphenols were preserved after adsorption but not when incorporated in situ. These results provide fruitful clues for the valorization of natural bioactive molecules in nanomedicine

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THE EFFECT OF FLURIDONE ON ACCUMULATION OF CAROTENOIDS, FLAVONOIDS AND PHENOLIC ACIDS IN RIPENING TOMATO FRUIT

Acta Scientiarum Polonorum Hortorum Cultus ◽

10.24326/asphc.2019.6.4 ◽

2019 ◽

Vol 18 (6) ◽

pp. 36-49

Author(s):

Wiesław Wiczkowski ◽

Justyna Góraj-Koniarska ◽

Marian Saniewski ◽

Marcin Horbowicz

Keyword(s):

Caffeic Acid ◽

Phenolic Acids ◽

Tomato Fruit ◽

Coumaric Acid ◽

Chlorogenic Acids ◽

Wide Strip ◽

First Time

We examined the response of maturing tomato fruit exposed for 7 days to fluridone (1-methyl-3-phenyl-5-[3-trifluoromethyl(phenyl)]-4(1H)-pyridinone). Fluridone was applied in lanolin paste in the form of a 2–3 mm wide strip from the top to the base of the fruit. As a control, a similar stripe of lanolin was applied in the same way on the opposite side of the same fruit. The content of major carotenoids, as well as flavonoids, and free and bound phenolic acids were determined using a HPLC and HPLC-MS-MS methods. Fluridone almost completely blocked the biosynthesis of lycopene and substantial declined content of ß-carotene and lutein in the tomato fruit. The fluridone caused a decreased content of quercetin, rutin and naringenin, and increased level of epicatechin. The herbicide did not affect the content of p-coumaric acid, but reduced the level of caffeic acid, both free and ester form, and declined the content of free ferulic and chlorogenic acids. Changes in phenolics composition observed for the first time indicate that fluridone interferes with the biosynthesis of further products of the metabolism of p-coumaric acid, both flavonoids and phenolic acids.

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Therapeutic Potential of Dietary Phenolic Acids

Advances in Pharmacological Sciences ◽

10.1155/2015/823539 ◽

2015 ◽

Vol 2015 ◽

pp. 1-10 ◽

Cited By ~ 33

Author(s):

Venkata Saibabu ◽

Zeeshan Fatima ◽

Luqman Ahmad Khan ◽

Saif Hameed

Keyword(s):

Phenolic Acids ◽

Defense Mechanism ◽

Therapeutic Potential ◽

Human Life ◽

Bioactive Molecules ◽

Negative Effects ◽

Synthetic Drugs ◽

Cellular Processes ◽

Novel Drugs ◽

Available Information

Although modern lifestyle has eased the quality of human life, this lifestyle’s related patterns have imparted negative effects on health to acquire multiple diseases. Many synthetic drugs are invented during the last millennium but most if not all of them possess several side effects and proved to be costly. Convincing evidences have established the premise that the phytotherapeutic potential of natural compounds and need of search for novel drugs from natural sources are of high priority. Phenolic acids (PAs) are a class of secondary metabolites spread throughout the plant kingdom and generally involved in plethora of cellular processes involved in plant growth and reproduction and also produced as defense mechanism to sustain various environmental stresses. Extensive research on PAs strongly suggests that consumption of these compounds hold promise to offer protection against various ailments in humans. This paper focuses on the naturally derived PAs and summarizes the action mechanisms of these compounds during disease conditions. Based on the available information in the literature, it is suggested that use of PAs as drugs is very promising; however more research and clinical trials are necessary before these bioactive molecules can be made for treatment. Finally this review provides greater awareness of the promise that natural PAs hold for use in the disease prevention and therapy.

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Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads ofCynara scolymusL. (cultivar Violetto di Provenza) in human subjects: a pilot study

British Journal Of Nutrition ◽

10.1017/s0007114507617218 ◽

2007 ◽

Vol 97 (5) ◽

pp. 963-969 ◽

Cited By ~ 85

Author(s):

E. Azzini ◽

R. Bugianesi ◽

F. Romano ◽

D. Di Venere ◽

S. Miccadei ◽

...

Keyword(s):

Ferulic Acid ◽

Chlorogenic Acid ◽

Caffeic Acid ◽

Peak Plasma ◽

Human Subjects ◽

Cholesterol Biosynthesis ◽

Plasma Concentrations ◽

Antioxidant Properties ◽

Hydroxycinnamic Acids ◽

Bioactive Molecules

The current growing interest for natural antioxidants has led to a renewed scientific attention for artichoke, due not only to its nutritional value, but, overall, to its polyphenolic content, showing strong antioxidant properties. The major constituents of artichoke extracts are hydroxycinnamic acids such as chlorogenic acid, dicaffeoylquinic acids caffeic acid and ferulic acid, and flavonoids such as luteolin and apigenin glycosides.Invitrostudies, using cultured rat hepatocytes, have shown its hepatoprotective functions andin vivostudies have shown the inhibition of cholesterol biosynthesis in human subjects. Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking. Results showed a plasma maximum concentration of 6·4 (sd 1.8) ng/ml for chlorogenic acid after 1 h and its disappearance within 2 h (P < 0·05). Peak plasma concentrations of 19·5 (sd6·9) ng/ml for total caffeic acid were reached within 1 h, while ferulic acid plasma concentrations showed a biphasic profile with 6·4 (sd1·5) ng/ml and 8·4 (sd4·6) ng/ml within 1 h and after 8 h respectively. We observed a significant increase of dihydrocaffeic acid and dihydroferulic acid total levels after 8 h (P < 0·05). No circulating plasma levels of luteolin and apigenin were present. Our study confirms the bioavailability of metabolites of hydroxycinnamic acids after ingestion of cooked edibleCynara scolymusL. (cultivar Violetto di Provenza).

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Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles

10.26434/chemrxiv.9925145 ◽

2019 ◽

Author(s):

Patrick Fier ◽

Suhong Kim ◽

Kevin M. Maloney

Keyword(s):

Functional Groups ◽

Late Stage ◽

Reductive Cleavage ◽

Bioactive Molecules ◽

General Method

Sulfonamides are pervasive in drugs and agrochemicals, yet are typically considered as terminal functional groups rather than synthetic handles. To enable the general late-stage functionalization of secondary sulfonamides, we have developed a mild and general method to reductively cleave the N-S bonds of sulfonamides to generate sulfinates and amines, components which can further react <i>in-situ</i> to access a variety of other medicinally relevant functional groups. The utility of this platform is highlighted by the selective manipulation of several complex bioactive molecules.

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Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

Current Organic Chemistry ◽

10.2174/1385272824999200407093625 ◽

2020 ◽

Vol 24 (8) ◽

pp. 900-908

Author(s):

Ram Naresh Yadav ◽

Amrendra K Singh ◽

Bimal Banik

Keyword(s):

Asymmetric Synthesis ◽

Chiral Auxiliary ◽

Bioactive Molecules ◽

One Pot ◽

Enantiomerically Pure ◽

Stereoselective Glycosylation ◽

One Pot Synthesis ◽

Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

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Structurally Related Edaravone Analogues: Synthesis, Antiradical, Antioxidant, and Copper-Chelating Properties

CNS & Neurological Disorders - Drug Targets ◽

10.2174/1871527318666191114092007 ◽

2020 ◽

Vol 18 (10) ◽

pp. 779-790 ◽

Cited By ~ 1

Author(s):

Alexandre LeBlanc ◽

Miroslava Cuperlovic-Culf ◽

Pier Jr. Morin ◽

Mohamed Touaibia

Keyword(s):

Oxidative Stress ◽

Amyotrophic Lateral Sclerosis ◽

Therapeutic Potential ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Therapeutic Options ◽

Partial Charge ◽

Associated Diseases ◽

Significant Interest ◽

Lateral Sclerosis

Background:: The current therapeutic options available to patients diagnosed with Amyotrophic Lateral Sclerosis (ALS) are limited and edaravone is a compound that has gained significant interest for its therapeutic potential in this condition. Objectives: : The current work was thus undertaken to synthesize and characterize a series of edaravone analogues. Methods: A total of 17 analogues were synthesized and characterized for their antioxidant properties, radical scavenging potential and copper-chelating capabilities. Results: Radical scavenging and copper-chelating properties were notably observed for edaravone. Analogues bearing hydrogen in position 1 and a phenyl at position 3 and a phenyl in both positions of pyrazol-5 (4H)-one displayed substantial radical scavenging, antioxidants and copper-chelating properties. High accessibility of electronegative groups combined with higher electronegativity and partial charge of the carbonyl moiety in edaravone might explain the observed difference in the activity of edaravone relative to the closely related analogues 6 and 7 bearing hydrogen at position 1 and a phenyl at position 3 (6) and a phenyl in both positions (7). Conclusion: Overall, this study reveals a subset of edaravone analogues with interesting properties. Further investigation of these compounds is foreseen in relevant models of oxidative stress-associated diseases in order to assess their therapeutic potential in such conditions.

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Flavonoids from the Genus Euphorbia: Isolation, Structure, Pharmacological Activities and Structure–Activity Relationships

Pharmaceuticals ◽

10.3390/ph14050428 ◽

2021 ◽

Vol 14 (5) ◽

pp. 428

Author(s):

Douglas Kemboi Magozwi ◽

Mmabatho Dinala ◽

Nthabiseng Mokwana ◽

Xavier Siwe-Noundou ◽

Rui W. M. Krause ◽

...

Keyword(s):

Therapeutic Potential ◽

Antioxidant Properties ◽

Structure Activity Relationship ◽

Biological Properties ◽

Therapeutic Agents ◽

Skeletal Structure ◽

Activity Relationship ◽

Hydroxyl Groups ◽

Structure Activity ◽

Review Reports

Plants of the genus Euphorbia are widely distributed across temperate, tropical and subtropical regions of South America, Asia and Africa with established Ayurvedic, Chinese and Malay ethnomedical records. The present review reports the isolation, occurrence, phytochemistry, biological properties, therapeutic potential and structure–activity relationship of Euphorbia flavonoids for the period covering 2000–2020, while identifying potential areas for future studies aimed at development of new therapeutic agents from these plants. The findings suggest that the extracts and isolated flavonoids possess anticancer, antiproliferative, antimalarial, antibacterial, anti-venom, anti-inflammatory, anti-hepatitis and antioxidant properties and have different mechanisms of action against cancer cells. Of the investigated species, over 80 different types of flavonoids have been isolated to date. Most of the isolated flavonoids were flavonols and comprised simple O-substitution patterns, C-methylation and prenylation. Others had a glycoside, glycosidic linkages and a carbohydrate attached at either C-3 or C-7, and were designated as d-glucose, l-rhamnose or glucorhamnose. The structure–activity relationship studies showed that methylation of the hydroxyl groups on C-3 or C-7 reduces the activities while glycosylation loses the activity and that the parent skeletal structure is essential in retaining the activity. These constituents can therefore offer potential alternative scaffolds towards development of new Euphorbia-based therapeutic agents.

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PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Journal of Chemical Research ◽

10.1177/1747519820987530 ◽

2021 ◽

pp. 174751982098753

Author(s):

Xiaofang Wu ◽

Lei Zhou ◽

Fangshao Li ◽

Jing Xiao

Keyword(s):

Acid Chloride ◽

Bioactive Molecules ◽

Mechanistic Studies ◽

One Pot ◽

Tert Butyl ◽

Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

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Biological Properties and Prospects for the Application of Eugenol—A Review

International Journal of Molecular Sciences ◽

10.3390/ijms22073671 ◽

2021 ◽

Vol 22 (7) ◽

pp. 3671

Author(s):

Magdalena Ulanowska ◽

Beata Olas

Keyword(s):

Body Weight ◽

Aromatic Compound ◽

Therapeutic Potential ◽

Antioxidant Properties ◽

Biological Properties ◽

Clove Oil ◽

Current State ◽

Potential Component ◽

Anti Inflammatory ◽

High Concentrations

Eugenol is a phenolic aromatic compound obtained mainly from clove oil. Due to its known antibacterial, antiviral, antifungal, anticancer, anti-inflammatory and antioxidant properties, it has long been used in various areas, such as cosmetology, medicine, and pharmacology. However, high concentrations can be toxic. A dose of 2.5 mg/kg body weight is regarded as safe. This paper reviews the current state of knowledge regarding the activities and application of eugenol and its derivatives and recent research of these compounds. This review is based on information concerning eugenol characteristics and recent research from articles in PubMed. Eugenol remains of great interest to researchers, since its multidirectional action allows it to be a potential component of drugs and other products with therapeutic potential against a range of diseases.

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Concentrations of Phenolic Acids Are Differently Genetically Determined in Leaves, Flowers, and Grain of Common Buckwheat (Fagopyrum esculentum Moench)

Plants ◽

10.3390/plants10061142 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1142

Author(s):

Alena Vollmannová ◽

Janette Musilová ◽

Judita Lidiková ◽

Július Árvay ◽

Marek Šnirc ◽

...

Keyword(s):

Chlorogenic Acid ◽

Caffeic Acid ◽

Phenolic Acids ◽

Sinapic Acid ◽

Fagopyrum Esculentum ◽

Blood Cholesterol ◽

Common Buckwheat ◽

High Concentration ◽

Phenolic Substances ◽

Fagopyrum Esculentum Moench

Common buckwheat (Fagopyrum esculentum Moench) is a valuable source of proteins, B vitamins, manganese, tryptophan, phytochemicals with an antioxidant effect, and the natural flavonoid rutin. Due to its composition, buckwheat supports the human immune system, regulates blood cholesterol, and is suitable for patients with diabetes or celiac disease. The study aimed to compare the allocation of selected phenolic acids (neochlorogenic acid, chlorogenic acid, trans-caffeic acid, trans-p-coumaric acid, trans-sinapic acid, trans-ferulic acid) and flavonoids (rutin, vitexin, quercetin, kaempferol) in the leaves, flowers, and grain of buckwheat cultivars of different origin. The content of individual phenolics was determined by the HPLC-DAD method. The results confirmed the determining role of cultivar on the relative content of chlorogenic acid, trans-caffeic acid, trans-sinapic acid, vitexin, and kaempferol in buckwheat plants. A significantly negative correlation among concentrations of phenolic acids in different common buckwheat plant parts shows that there are different mechanisms of genetic influences on the concentration of phenolic substances in common buckwheat flowers, leaves, and grain. These differences should be taken into account when breeding buckwheat for a high concentration of selected phenolic substances.

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