Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract

Polyphenolic compounds such as eriocitrin, luteolin-7-O-rutinoside, diosmin, hesperidin, narirutin, isorhoifolin, rosmarinic and caffeic acids were identified in an aqueous extract (Ex) obtained from peppermint leaves (Menthae x piperitae folium). The content of polyphenols in Ex was as follows: eriocitrin 38%, luteolin-7-O-rutinoside 3.5%, hesperidin 2.9%, diosmin 0.8%, isorhoifolin 0.6%, narirutin 0.3%, rosmarinic acid 3.7% and caffeic acid 0.05%. The strongest antiradical activity (determined as DPPH* scavenging features) was observed for luteolin-7-O-rutinoside, eriocitrin and rosmarinic acid. Caffeic acid and hesperidin revealed a lower antiradical activity while isorhoifolin, narirutin and diosmin showed the lowest activity. The strongest anti-H2O2 activity was observed for eriocitrin, a little lower for rosmarinic acid. The rate of hydrogen peroxide scavenging activity displayed by luteolin-7-O-rutinoside and caffeic acid was lower than that of rosmarinic acids. Hesperidin appeared to be a very weak scavenger of hydrogen peroxide. Almost no anti-H2O2 activity was demonstrated for diosmin, narirutin and isorhoifolin. Among examined flavonoids, the strongest antiradical and anti-H2O2 activity was shown for compounds with two hydroxy groups bound to the Bring in ortho position in relation to each other. Replacement of one hydroxy group in the Bring with a methoxy group or removing one hydroxy group leads to decrease of antiradical and anti-H2O2 activity of flavonoids. Our results suggest that eriocitrin is a powerful peppermint antioxidant and a free radical scavenger.     

Quantitative determination of flavonoid content in the aerial part of Baical scullcap (<Emphasis Type="Italic">Scutellaria baicalensis</Emphasis> Georgi)

A pharmacognostic study of aerial parts of Scutellaria baicalensis Georgi (Lamiaceae family) has been carried out. A merchandising analysis has been performed to determine the basic quality parameters of S. baicalensis. A chemical composition analysis has revealed the presence of organic acids, free carbohydrates, polysaccharides, amino acids, alkaloids, flavonoids, phenolic acids, anthocyanins, tannins, photosynthetic pigments, lipids, and triterpene compounds. Ethyl acetate and ethanol fractions, extracted from the aerial parts of S. baikalensis, have shown a significant antiradical activity.     

Changes in composition of phenolic compounds and antioxidant properties of <Emphasis Type="Italic">Vitis amurensis</Emphasis> seeds germinated under osmotic stress

The research focused on the changes of phenolic compounds as well as their antiradical activity and reducing power isolated from Amur grape (Vitis amurensis) seeds during germination under optimal conditions and under osmotic stress. The seeds were found to contain tannins, (+) catechin, (−) epicatechin, and gallic acid (in free, ester- and glycoside-bound forms). Extracts from the seeds were also shown to contain two other phenolic acids: caffeic and p-coumaric acids, in very low levels. During a 3-day seed germination test under osmotic stress (−0.5 MPa), the content of total phenolics, tannins and phenolic acids declined as compared to the control. However, seed germination under stress conditions led to a significant increase in the amount of catechins. Because catechin is the one of the units in condensed tannins, its dynamic increase during seed germination may be involved in metabolism of tannins under osmotic stress. It is also likely that the synthesis of catechins is greater under stress conditions and these compounds may be engaged in the process of acclimatization of grapevines to stress conditions. The content of total phenolic compounds in seed extracts is positively correlated with their antioxidant properties. The extracts from seeds germinated under optimal conditions exhibited strong antiradical properties against the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical as well as reducing power. As regards the extracts from grape seeds germinated under osmotic stress, this capability was much weaker. The research demonstrated that antioxidants could interfere with the oxidation process induced by various stresses by acting as oxygen scavengers, therefore the tolerance to drought stress might be correlated with an increase in the antioxidant potential.     

Identification of aromatic dihydroxy acids in biological fluids

3,5-Dihydroxyphenylpropionic acid, 3,5-dihydroxycinnamic acid and 2,3-dihydroxycinnamic acid were detected for the first time to be components of human urine. In the course of this investigation all constitutional isomers of dihydroxy-benzoic, -phenylpropionic, -phenylacetic and -cinnamic acid were synthesized. Mass spectra and retention indices of methyl and trimethylsilyl (TMS) derivatives were determined. In contrast to many other substituted aromatic compounds the mass spectra of methyl and TMS derivatives of dihydroxy aromatic acids often allow a firm distinction to be made between constitutional isomers: TMS derivatives of aromatic acids containing two hydroxy groups located in the ortho position to each other can be recognized by ions resulting from a primary cleavage reaction mainly in the side chain or ester group, followed by loss of tetramethylsilane. In methyl derivatives of 1,2,3-trisubstituted isomers, methoxy groups are lost much more easily from the ions corresponding to the benzylic cleavage than in other isomers. Methyl derivatives of dihydroxycinnamic acids containing at least one methoxy group in the ortho position to the side chain are characterized by a fragmentation reaction, corresponding to the loss of dimethyl ether. TMS and methyl derivatives of 3,5-dihydroxy aromatic acids show unique structure-specific fragmentation reactions.     

Pharmacognostic study of aerial parts of Baikal skullcap (<Emphasis Type="Italic">Scutellaria baicalensis</Emphasis> Georgi)

A pharmacognostic study of aerial parts of Scutellaria baicalensis Georgi (Lamiaceae family) has been carried out. A merchandising analysis has been performed to determine the basic quality parameters of S. baicalensis. A chemical composition analysis has revealed the presence of organic acids, free carbohydrates, polysaccharides, amino acids, alkaloids, flavonoids, phenolic acids, anthocyanins, tannins, photosynthetic pigments, lipids, and triterpene compounds. Ethyl acetate and ethanol fractions, extracted from the aerial parts of S. baikalensis, have shown a significant antiradical activity.     

植物多酚的防癌抗癌作用

植物多酚是植物中广泛存在的一大类多酚化合物的总称,包括多酚（如单宁）、黄酮、酚酸等。体外实验研究表明植物多酚对多种人癌细胞具有增殖抑制作用,抑制动物体内肿瘤生长。其作用机理与抗氧化、调控细胞周期、诱导肿瘤细胞凋亡和分化、影响血管生成和肿瘤细胞信号传导等有关。对植物多酚的防癌抗癌作用,值得进一步深入研究。     

Phytochemical Analysis and Antioxidant Activity of <i>Crocus speciosus</i> Leaves

The numerous studies indicate leaves of plants are a rich source of bioactive compounds that can be a valuable source of compounds used in the pharmaceutical and cosmetic industries. Aim of this study was to investigate the chemical composition and the antioxidant property of Crocus speciosus leaves. Primary phytochemical screening of C. speciosus leaves revealed the presence of some following compound categories such as phenolic compounds, aminoacids, saponins, proteins, tannins, triterpenoids, glycosides, polysaccharides. The total flavonoids and phenolic compounds content were determined spectrophotometrically and by HPLC-DAD and HPLC-MS. Antiradical activity was determined by ABTS radical-cation scavenging method, spectrophotometrically. The total amount of flavonoids in C. speciosus leaves was 1.07 ± 0.02 mg RE/g (p < 0.05), the total amount of phenolic compounds was 0.41 ± 0.01 mg GAE/g (p < 0.05). By HPLC-DAD-MS analysis the presence of the mangiferin, chlorogenic acid, isoorientin, kaempferol, hyperoside, and isoquercitin was established for the first time in Crocus leaves. The antiradical activity of C. speciosus leaves extracts was 150.08 ± 4.5 μmol/g (p < 0.05) and its was mainly attributed to phenolic compounds content. The high amounts of flavonoids and antiradical activity in C. speciosus leaves suggests promising phytochemical and pharmacological study of this Crocus species.     

Structure-activity relationships in a series of melatonin analogues with the low-density lipoprotein oxidation model

Despite an increasing number of publications concerning the antioxidant activity of melatonin, little is known about the structural features responsible for this kind of activity. To understand the role played by the different elements of melatonin structure in its antioxidant activity, we have designed and tested several compounds related to this molecule in the low-density lipoprotein peroxidation model. We present here the results of this study in terms of structure-activity relationships focusing on the influence of the acetamidoethyl side chain, the methoxy group, and the indole heterocycle. In this model, we found that changing the acyl residue generally resulted in more active products. We obtained particularly good results with the nonanoyl derivative which showed a level of activity comparable to that of phenols despite lacking a phenolic function. The presence of a methoxy group in position 5 generally had a beneficial influence on the activity, but when located in position 6, the effects were various. The substitution of a hydroxy for the methoxy group led to phenolic compounds endowed with very high antioxidant activity. Replacing the amide with a ketone function did not affect the activity while replacement with an amine group in some cases resulted in prooxidant compounds. Finally, we compared the efficacy of different aromatic rings. The indole heterocycle proved to be better than benzofurane and naphthalene rings.     

荔枝果皮抗氧化作用研究

成熟和未成熟荔枝(生理落果)皮提取物均有很强的抗氧化活性,抗氧化性随添加量的增加而增强,0．04％提取物的抗氧化效果优于0．02％BHT;磷酸具有抗氧化增效作用;初步推断抗氧化成分中有酚酸、黄酮类物质。     

Antioxidative properties of Jaffa sweeties and grapefruit and their influence on lipid metabolism and plasma antioxidative potential in rats

The effective substances (polyphenols, phenolic and ascorbic acids, flavonoids and dietary fibers) and antioxidative activities, using different radical-scavenging tests, were determined for Jaffa sweeties and grapefruit. The antioxidative activities comprised the contributions from polyphenols, phenolic acids, flavonoids and ascorbate components, and were well-correlated with polyphenols and flavonoids. The correlation coefficient between the polyphenols and antioxidative activity varied from 0.73 to 0.99. All applied methods showed that sweeties had higher antioxidative activity than grapefruit. Experiments on laboratory animals show that diets supplemented with sweeties, and to a lesser extent with grapefruit, increased the plasma antioxidative potential and improved the lipid metabolism, especially in the rats fed with added cholesterol. These findings provide additional characterization of the nutritional value of citrus fruits and their influence on the lipid metabolism in rats.     

Microbial metabolism of dietary phenolic compounds in the colon

Plant foods contain substantial amounts of phenolic compounds. Dietary interventions with phenolic supplementation show that phenolic compounds are transformed into phenolic acids or lactone structures by intestinal microbiota. The colon is the main site of microbial fermentation. The metabolites circulate in plasma and are excreted via urine. The entero-hepatic circulation ensures that their residence time in plasma is extended compared to that of their parent compounds. Thus these metabolites may exert systemic effects, which however have not been studied adequately. In particular the health implications of microbial metabolites of flavonoids, mostly phenolic acids, are unknown. This review aims to elucidate the microbial metabolism of most of the phenolic classes: flavonoids, isoflavonoids, lignans, phenolic acids and tannins. Some examples of biological activity studies of flavonoid and lignan metabolites are given. Biological significance of enterolactone, a mammalian plant lignan metabolite, has been studied quite extensively, but convincing evidence of the health benefits of the diverse pool of microbial metabolites is still scarce. Hopefully, novel tools in systems biology and the constant search for biomarkers will elucidate the role of the phenolic metabolome in health and in the prevention of chronic diseases. In conclusion, the colon is not only an excretion route, but also an active site of metabolism and deserves further attention from the scientific community.     

Quantitative analysis of polyphenols and antioxidant activity in four Daphne L. species

The content of biologically active phenolic compounds (total polyphenols, tannins, flavonoids, and phenolic acids) were determined using spectrophotometry in four wild Croatian species of Daphne L. in the family Thymelaeaceae (Daphne alpina, D. cneorum, D. laureola, and D. mezereum). The concentration of total flavonoids (TF) was highest in the leaves of these Daphne species (0.12?C0.51% dry herb weight, DW) whereas the content of other phenolic compounds analyzed were highest in the roots, including total polyphenols (TP; 2.71?C19.03% DW), tannins (T; 1.14?C7.39% DW), and total phenolic acids (TPA; 0.12?C0.87% DW). D. alpina contained the highest amount of polyphenols, with the exception of flavonoids, where maximum concentrations were found in D. laureola. We also examined the antioxidant activity of leaf, stem, and root extracts. All extracts analyzed demonstrated high free radical scavenging activity with the highest concentration in the leaf extracts of D. alpina. Leaf extracts of D. cneorum showed the highest antioxidant activity in a ??-carotene bleaching assay.     

The lignicolous fungus Trametes versicolor (L.) Lloyd (1920): a promising natural source of antiradical and AChE inhibitory agents

This study aimed to determine antiradical (DPPH^? and ^?OH) and acetylcholinesterase (AChE) inhibitory activities along with chemical composition of autochtonous fungal species Trametes versicolor (Serbia). A total of 38 phenolic compounds with notable presence of phenolic acids were identified using HPLC/MS-MS. Its water extract exhibited the highest antiradical activity against ^?OH (3.21?μg/mL), among the rest due to the presence of gallic, p-coumaric and caffeic acids. At the concentration of 100?μg/mL, the same extract displayed a profound AChE inhibitory activity (60.53%) in liquid, compared to donepezil (89.05%), a drug in clinical practice used as positive control. The flavonoids baicalein and quercetin may be responsible compounds for the AChE inhibitory activity observed. These findings have demonstrated considerable potential of T. versicolor water extract as a natural source of antioxidant(s) and/or AChE inhibitor(s) to be eventually used as drug-like compounds or food supplements in the treatment of Alzheimer’s disease.     

Stable free radical scavenging and antiperoxidative properties of resveratrol compared in vitro with some other bioflavonoids

Stable free radical scavenging and antiperoxidative activities of resveratrol, a component of grapes and red wine, were evaluated and compared with some other known bioflavonoids (quercetin, catechin, kaempferol, myricetin, fisetin, ellagic acid and naringenin) widely present in the plant kingdom. Free radical scavenging activity was measured in an in vitro chemical system (DPPH assay), while for antiperoxidative activity, biological system comprising of hepatic and pulmonary homogenates was employed. Antiradical activity assay showed quercetin and myricetin to be stronger antiradical agents than resveratrol. Structure-activity study revealed that O-dihydroxy group on ring B of flavonoid plays a crucial role. A double bond at 2-3 position conjugated with a 4-oxo function and hydroxy groups at positions 3 and 5 also contribute towards antiradical activity of flavonoids. Resveratrol exhibited stronger antiradical activity than kaempferol and naringenin and was also more efficient than alpha-tocopherol, a known strong endogenous non-flavonoid antioxidant, used for comparison. In vitro antiperoxidative assay showed fisetin as the strongest and kaempferol as the weakest antioxidant. Resveratrol was found to be stronger antioxidant than catechin, myricetin, kaempferol and naringenin, but was weaker than quercetin, fisetin and alpha-tocopherol. Antiradical and antiperoxidative activities of resveratrol may explain its beneficial effects in disease states. Assays exhibited no direct correlation between antiradical and antiperoxidative activities of the phenolics.     

Caffeoylquinic Acids: Separation Method,Antiradical Properties and Cytotoxicity

Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C‐4 position showed higher antiradical activity compared to acylation at C‐3 or C‐5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4‐caffeoylquinic acid. Excepted to 3,4‐dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C‐4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.     

The ortho hydroxy-amino group: another choice for synthesizing novel antioxidants

Four ortho hydroxy-amino derivatives have been designed based on the structures of flavonoids to explore the effect of the ortho hydroxy-amino group on the antioxidant properties of molecules, and their bond dissociation enthalpies (BDE), ionization potentials (IP), the highest occupied molecular orbitals (HOMO), and spin densities have been calculated. The results reveal that the ortho hydroxy-amino group plays an important role in promoting the antioxidant properties of molecules because of its lowering effect on BDE, IP, and spin density. The derivatives with ortho hydroxy-amino group show stronger antioxidant activity than the derivatives with mono hydroxy or ortho dihydroxy group. Thus, the ortho hydroxy-amino group can be used as another potential functional group to synthesize novel antioxidants as guessed.     

Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells

To search for a new class of antidiabetic compounds, effects of 44 flavonoids on the adipogenesis of 3T3-L1 cells were examined. Among them, 3,4',7-trimethylkaempferol, tetramethylkaempferol, and pentamethylquercetin concentration-dependently enhanced the accumulation of triglyceride, a marker of adipogenesis. With regard to structural requirements of flavonoids for the activity, it was fond that: (1) most flavonoids having hydroxy groups lacked the effect; (2) flavonols with methoxy groups showed stronger effects particularly those with a methoxy group at the 3-position; and (3) a methoxy group of flavonols at the B ring was also important. 3,4',7-Trimethylkaempferol, tetramethylkaempferol, and pentamethylquercetin significantly increased the amount of adiponectin released into the medium and the uptake of 2-deoxyglucose into the cells. Furthermore, tetramethylkaempferol and pentamethylquercetin also increased mRNA levels of adiponectin, glucose transporter 4 (GLUT4), and fatty acid-binding protein (aP2). Both compounds also increased the mRNA levels of peroxisome proliferator-activated receptor (PPAR)γ2 and CCAAT/enhancer-binding protein (C/EBP)α, β, and/or δ, although, different from troglitazone, they did not activate PPARγ directly in a nuclear receptor cofactor assay.     

The chemical constituents and economic plants of the Euphorbiaceae

The chemical constituents and economic plants of the Euphorbiaceae. A chemical review of the different classes of compounds which have been isolated from the Euphorbiaceae (other than the diterpenoids) is given. This includes triterpenoids and related compounds (sterols, alcohols and hydrocarbons), phenolic compounds (flavonoids, lignans, coumarins, tannins, phenanthrenes, quinones, phenolic acids, etc.), alkaloids, cyanogenic glucosides and glucosinolates. A summary of the industrial and medicinal uses of members of the Euphorbiaceae is provided.     

Investigations on fungicides. XX. The fungitoxicity of analogues of the phy toalexin 2-(2' -methoxy-4' -hydroxyphenyl)-6-methoxybenzofuran(vignafuran)

A series of hydroxy-and methoxy-2-phenyl benzofurans, structurally related to the phytoalexin vignafuran, have been synthesised and their antifungal activity assessed both as inhibitors of spore germination in vitro and as protective foliar sprays against three pathogens. All fungitoxic compounds have a hydroxy group in the molecule although most di- and tri-hydroxy compounds were inactive. Methoxy compounds were inactive but substituting methoxy groups into the molecule of monohydroxy compounds sometimes enhanced their fungitoxicity. No close correlation was established between antifungal activity and either Hansen n values or the n.m.r. chemical shift of the phenolic protons.     

Changes in the composition of phenolic compounds and antioxidant properties of grapevine roots and leaves (Vitis vinifera L.) under continuous of long-term drought stress

Grapevine seedlings Vitis vinifera L. were grown in a greenhouse under optimum conditions (soil moisture ca 70 %) and under drought stress (soil moisture ca 30 %). Drought stress caused reduction in total phenolic compounds in grapevine leaves and roots, where were identified tree phenolic acids: caffeic acid, p-coumaric acid and ferulic acid. All acids found in leaves and roots occurred in the ester-bound form. Only caffeic acid in leaves appeared in the free and ester-bound form. Caffeic acid was present in the highest concentrations. The content of ferulic acid was the lowest in both tissues. The levels of all phenolic acids in leaves and roots decreased significantly under the drought stress. All the extracts from grapevine leaves and roots had antioxidative properties, but the antiradical activity of the extracts obtained from roots subjected to drought stress was lower to the control. The results of the analysis revealed that long-term drought stress caused a decrease in selected elements of secondary metabolism in such a different plant tissues that are the leaves and roots of the grapevine.