Chemical Components of Oxytropis pseudoglandulosa Induce Apoptotic-Type Cell Death of Caco-2 Cells.

Oxytropis pseudoglandulosa plant is used in traditional Mongolian medicine. However, its chemical composition and biological properties are poorly explored. In this study, the total content of polyphenols and flavonoids as well as antioxidant activity were verified in plant extract. The total phenolic and flavonoid contents were determined by spectrometric (6.62 mg GAE/g and 10.32 mg QE/g) and chromatographic (17,598 mg/kg and 17,467 mg/kg) assays. The antioxidant potential was investigated by DPPH assay and yielded IC50 at 18.76 µg/mL. Twelve phenolic compounds were identified as components of O. pseudoglandulosa extract. Kaempferol-3-O-robinosyl-7-O-rhamnoside and kaempferol-3-(p-coumaroyl)-rutinosyl-7-rhamnoside made up 80% of determined components and were found to be the major polyphenolic compounds. The biological properties of O. pseudoglandulosa extracts were determined in vitro using human epithelial adenocarcinoma Caco-2 cell line. Low concentrations of extract (0-30 µg/mL) exhibited protective effects against cell damage caused by chemically induced oxidative stress. Elevated concentrations, on the other hand, resulted in apoptotic-type cell death induction. Metabolic failure, ROS elevation and membrane permeabilization observed in cells upon incubation with extract dosages above 50 µg/mL allowed us to conclude on O. pseudoglandulosa being predominantly a necrosis inducer.

Flavonoid Glycosides in Brassica Species Respond to UV-B Depending on Exposure Time and Adaptation Time.

Recently, there have been efforts to use ultraviolet-B radiation (UV-B) as a biotechnological tool in greenhouses. Leafy Brassica species are mainly considered for their ability to synthesize glucosinolates and are valued as baby salads. They also have a remarkable concentration of chemically diverse flavonoid glycosides. In this study, the effect of short-term UV-B radiation at the end of the production cycle was investigated without affecting plant growth. The aim was to verify which exposure and adaptation time was suitable and needs to be further investigated to use UV as a biotechnological tool in greenhouse production of Brassica species. It is possible to modify the flavonoid glycoside profile of leafy Brassica species by increasing compounds that appear to have potentially high antioxidant activity. Exemplarily, the present experiment shows that kaempferol glycosides may be preferred over quercetin glycosides in response to UV-B in Brassica rapa ssp. chinensis, for example, whereas other species appear to prefer quercetin glycosides over kaempferol glycosides, such as Brassica oleracea var. sabellica or Brassica carinata. However, the response to short-term UV-B treatment is species-specific and conclusions on exposure and adaptation time cannot be unified but must be drawn separately for each species.

Effects of Different Drying Methods on Untargeted Phenolic Metabolites, and Antioxidant Activity in Chinese Cabbage (Brassica rapa L. subsp. chinensis) and Nightshade (Solanum retroflexum Dun.).

Chinese cabbage (Brassica rapa L. subsp. chinensis) and Nightshade (Solanum retroflexum are popular traditional leafy vegetables consumed predominantly by rural Africans. Sun drying is adopted as a traditional method of postharvest preservation to store theses leaves during off seasons. The influence of different types of postharvest processing treatments, such as conventional oven drying, solar cabinet drying, sun drying and freeze drying, on the changes on colour properties and antioxidant components were investigated. Freeze-drying retained the ascorbic acid content, antioxidant activities, total chlorophyll content, green colour by reducing the colour difference (∆E). With regard to Chinese cabbage and Nightshade leaves, sun and microwave drying respectively had the most negative impact on all the identified phenolic compounds. The OPLS-DA and the UPLC-QTOF/MS and chemometric approach showed kaempferol-3-O-sophoroside, kaempferol-3-sophorotrioside-7-glucoside and hydroxyoctadecenedioic acid as the markers responsible for the separation of sun-dried samples from the other drying treatments in Chinese cabbage. Sinapoyl malate was not detected in sun-dried samples. Caffeoylmalic acid was identified as the marker compound to separate the other drying treatments from the microwave dried samples of Nightshade leaves. Trihydroxyoctadecadiene derivative and hydroxyoctadecanedioic acid were detected in microwaved samples. Due to the cost effectiveness, solar dryer cabinet treatment was recommended for drying both vegetables. The proximate analysis of solar dried functional powder of Chinese cabbage and Nightshade vegetables demonstrated higher contents of protein and dietary fibre.

Changes in the profiling of bioactive components with the roasting process in Lycium chinense leaves and the anti-obesity effect of its bioaccessible fractions.

BACKGROUND: This study aimed to investigate the profiles of bioactive components in roasted Lycium chinense leaves (LCLs) and its in vitro anti-obesity activity after digestion processes. RESULTS: Chlorogenic acid, kaempferol-3-sophoroside-7-glucoside, kaempferol-3-sophoroside, and kaempferol-3-glucoside were discovered as bioactive components in various ratios of ethanol (EtOH) extract in LCLs by using ultra-performance liquid chromatography-electrospray ionization-mass spectrophotometry (UPLC-ESI-MS). The roasting process followed by a 30% EtOH extraction tended to decrease the content of chlorogenic acid and kaempferol-3-glucoside, and enhanced the content of kaempferol-3-sophoroside-7-glucoside. It effectively inhibited pancreatic lipase activity by 62.50 ± 4.81%, which was approximately 1.71 percentage points higher than that of the dried-nonroasted LCL extract (60.79 ± 3.75%). Its bioaccessible fraction obtained from in vitro digestion significantly and dose dependently reduced intracellular lipid accumulation by adipocyte 3T3-L1 compared with a 30% EtOH extraction. At a concentration of 200 µg mL-1 , it inhibited lipid accumulation up to 29.55% in 3T3-L1 cells, which indicated that human digestive enzymes converted kaempferol-3-sophoroside-7-glucoside to kaempferol metabolites that have anti-obesity effects. CONCLUSION: This study suggests that the profiling of bioactive components by processing methods and a bioaccessible fraction could be crucial to improve the bioactivity of LCLs, and potentially be a natural anti-obesity ingredient after oral intake. © 2019 Society of Chemical Industry.

New Hydrogels Enriched with Antioxidants from Saffron Crocus Can Find Applications in Wound Treatment and/or Beautification.

Saffron extracts have a long history of application as skin protectant, possibly due to their ability to scavenge free radicals. In this work, the performance of a hydrogel enriched with antioxidant compounds isolated from saffron crocus (Crocus sativus L.) petals was tested. These hydrogels could be considered as new drug delivery system. Hydrogels are crosslinked polymer networks that absorb large quantities of water but retain the properties of a solid, thus making ideal dressings for sensitive skin. We tested antioxidant-enriched hydrogels on primary mouse fibroblasts. Hydrogels enriched with kaempferol and crocin extracted from saffron petals showed good biocompatibility with in vitro cultured fibroblasts. These new types of hydrogels may find applications in wound treatment and/or beautification.

Modulation of flavonoid metabolites in Arabidopsis thaliana through overexpression of the MYB75 transcription factor: role of kaempferol-3,7-dirhamnoside in resistance to the specialist insect herbivore Pieris brassicae.

Anthocyanins and flavonols are secondary metabolites that can function in plant defence against herbivores. In Arabidopsis thaliana, anthocyanin and flavonol biosynthesis are regulated by MYB transcription factors. Overexpression of MYB75 (oxMYB75) in Arabidopsis results in increasing anthocyanin and flavonol levels which enhances plant resistance to generalist caterpillars. However, how these metabolites affect specialist herbivores has remained unknown. Performance of a specialist aphid (Brevicoryne brassicae) was unaffected after feeding on oxMYB75 plants, whereas a specialist caterpillar (Pieris brassicae) gained significantly higher body mass when feeding on this plant. An increase in anthocyanin and total flavonol glycoside levels correlated negatively with the body mass of caterpillars fed on oxMYB75 plants. However, a significant reduction of kaempferol-3,7-dirhamnoside (KRR) corresponded to an increased susceptibility of oxMYB75 plants to caterpillar feeding. Pieris brassicae caterpillars also grew less on an artificial diet containing KRR or on oxMYB75 plants that were exogenously treated with KRR, supporting KRR's function in direct defence against this specialist caterpillar. The results show that enhancing the activity of the anthocyanin pathway in oxMYB75 plants results in re-channelling of quercetin/kaempferol metabolites which has a negative effect on the accumulation of KRR, a novel defensive metabolite against a specialist caterpillar.

Antioxidant Activities in Kenaf (Hibiscus cannabinus) Shoots during Growth Stages and Destination of Chlorogenic Acid and Kaempferol Glycosides.

Apart from being utilized as a commercial fiber at maturity, kenaf shoots have potential as a food and feed source because of their diverse bioactivities. Previous studies have focused on mature stems because of their high biomass, whereas the antioxidant activities (AA) and the destination of AA contributors of kenaf stems and their high-yielding byproduct leaves during the growth stage have rarely been studied. Therefore, we investigated changes in AA and its relative components in kenaf leaves and stems during the four vital growth stages. Higher ABTS radical cation and DPPH radical scavenging abilities and ferric reducing antioxidant power, total phenolic content, total flavonoid content, and total polysaccharide content were observed at all leaf stages and in the late stem stages. Chlorogenic acid (CGA) and kaempferol glycosides, especially kaempferitrin (Kfr), were identified as representative phenolic acids and flavonoids in both kenaf leaves and stems. The content of CGA in both leaves and stems increased corresponding to the plant's growth stage, whereas kaempferol glycosides were enhanced in leaves but declined in stems. The highest correlation was observed between TPC and AA in all organs. Further evaluation of CGA and Kfr verified that CGA was the predominant contributor to AA, surpassing Kfr. These findings suggest that kenaf leaves increase antioxidant levels as they grow and can be a useful source of stem harvesting byproducts.

Thermal Stability of Anisoyl Kaempferol Glycosides in Jack Bean (Canavalia ensiformis (L.) DC) and Their Effect on α-Glucosidase Inhibition.

Kaempferol glycosides are functional components of jack bean. The chemical stability of kaempferol glycosides under simulated food processing conditions was evaluated in this study by subjecting the methanol extract and each compound to heat treatment. During the heat treatment, rearrangement of the anisoyl group on the rhamnose moiety of the kaempferol glycoside was observed, followed by hydrolysis upon long-term heat treatment. One of the two regioisomers produced under heating conditions showed higher α-glucosidase inhibitory activity than the dominant anisoyl kaempferol glycoside. This rearrangement reaction was also observed upon the heat treatment of methyl-3-O-anisoyl-rhamnose, with the rearrangement from the 3-position to the 2-position occurring preferentially. The approach adopted in this study can be used to design appropriate food processing conditions, which, in turn, will increase the functional value of foods.

Bioactivity Potential of Aesculus hippocastanum L. Flower: Phytochemical Profile, Antiradical Capacity and Protective Effects on Human Plasma Components under Oxidative/Nitrative Stress In Vitro.

Horse chestnut (Aesculus hippocastanum) flower is a traditional medicine applied to alleviate symptoms of chronic venous insufficiency (CVI). However, its flavonoid-based composition has not been sufficiently recognized, and the data supporting its traditional application are lacking. In the work, 43 constituents were detected by UHPLC-PDA-ESI-TQ-MS/MS (flavonoids, phenolic acids, flavanols, and coumarins), including 31 reported in the flower for the first time. The quantitative HPLC-PDA study (developed and validated for quality control purposes) indicated the fractionated extraction as an efficient method for enhancing the total polyphenol content (TPHC) in the extracts (up to 414.06 mg/g) and kaempferol glycosides as their dominant constituents (75.05-82.14% TPHC). The activity studies showed significant scavenging properties of the extracts and their constituents towards reactive oxygen species (especially against highly reactive hydroxyl radical, with capacities up to 7.85 mmol ascorbic acid equivalents/g). Moreover, the analytes relevantly protected human plasma biomolecules from peroxynitrite-induced oxidative/nitrative damage; at 1-50 µg/mL, they hindered the protein nitration and lipid peroxidation, decreasing the levels of 3-nitrotyrosine (by up to 50%) and thiobarbituric acid reactive substances (by up to 70%), respectively. The extracts also averted the depletion of plasma thiols (by up to 67%) and improved the non-enzymatic antioxidant capacity of plasma. The demonstrated mechanisms might be partly responsible for the efficacy of the flower in CVI. Additionally, the anti-aggregatory and anticoagulant properties of the extracts were found only mild or negligible, which suggests that they may be safely applied with drugs impacting the coagulation process.

Effects of UV-A radiation on organ-specific accumulation and gene expression of isoflavones and flavonols in soybean sprout.

Organ-specific flavonoid destination in soybean sprouts following UV irradiation is still unclear although the metabolic pathway of flavonoid synthesis and UV responded flavonoid accumulation have been well investigated. We report the identification of organ-specific localization and specific gene expression of isoflavones and kaempferol glycosides in the soybean sprouts responded to UV-A irradiation. UV-A irradiation stimulated only root isoflavones, especially increase of genistein types. The daidzein types predominated in non-UV-A treated roots. Kaempferol glycosides were not increased in roots by UV-A, but distinctly increased in aerial organs, especially in the cotyledons. These results demonstrate that UV-A upregulates the naringenin pathway synthesizing genistin and kaempferol rather than the liquiritigenin pathway synthesizing daidzin and glycitin. High GmUGT9 and other gene expression related to isoflavone synthesis in roots clearly demonstrate the UV-A-induced isoflavone accumulation. Aerial organ specific increase of GmF3H, GmFLS1, and GmDFR1 expression by UV-A distinctly demonstrates the flavonol increase in aerial organs.

Activation of caspase-3 in gastric adenocarcinoma AGS cells by Xylopia aethiopica (Dunal) A. Rich. fruit and characterization of its phenolic fingerprint by HPLC-DAD-ESI(Ion Trap)-MSn and UPLC-ESI-QTOF-MS2.

While the fruits of Xylopia aethiopica (Dunal) A. Rich. are important in African countries as a local trade product, their composition remains scarcely investigated. Phenolic fingerprint is herein delivered through HPLC-DAD-ESI(Ion Trap)-MSn and UPLC-ESI-QTOF-MS2 analysis, six cinnamoylquinic acid derivatives and twenty-four flavonoid glycosides being determined, chrysoeriol-7-O-glycosides being the main constituents. A cytotoxicity screening of twenty-eight hydroethanol extracts, obtained from a collection of Guinea-Bissauan plants, against A549 and AGS carcinoma cells, revealed the selective and potent effect towards AGS cells (IC50 = 151 × 10-3 g L-1), upon exposure to the extract from X. aethiopica fruits. Additional experiments demonstrated insignificant effect on LDH release at 151 × 10-3 g L-1, morphological analysis further suggesting induction of apoptosis. Pro-apoptotic effects were confirmed, as the extract enabled the activation of the effector caspase-3, broadening the knowledge on the anticancer mechanisms elicited by the fruits of X. aethiopica. Phenolic constituents might contribute to the cytotoxic effects, particularly via caspase-3 activation. Considering that X. aethiopica fruit is very often referred as an anticancer ingredient in Africa, but mainly the potent cytotoxicity herein recorded, our results call for additional research aiming to identify non-phenolic constituents contributing to the effects and also to further detail the anticancer mechanisms.

Gustavia gracillima Miers. flowers effects on enzymatic targets underlying metabolic disorders and characterization of its polyphenolic content by HPLC-DAD-ESI/MSn.

Notwithstanding Gustavia gracillima Miers widespread distribution in neotropical regions, its chemical profile and biological properties remain uninvestigated. A methanol extract obtained from the flowers was characterized through HPLC-DAD-ESI/MSn, nine ellagic acid derivatives and twelve kaempferol 3-O-glycosides being identified and quantitated for the first time at the species and genus. Preliminary cytotoxicity screening did not reveal noticeable effects upon gastrointestinal representative cell lines (AGS, Caco-2 and Hep G2), which further prompted us to evaluate the impact in a series of targets involved in metabolic disorders and associated complications. Despite of the moderate inhibition towards 5-lipoxygense activity, G. gracillima methanol extract displayed significant effects on carbohydrates-hydrolysing enzymes. In contrast with the antidiabetic reference drug acarbose, the extract was able to selectively inhibit yeast α-glucosidase activity (IC50 = 4.72 µg/mL), with negligible inhibitory effects upon α-amylase. Kinetic studies pointed to a model of mixed inhibition with a great binding activity, characterized by an inhibitory constant of 2.91 µg/mL. The notable inhibitory activity was also confirmed in α-glucosidase homogenates isolated from human intestinal cells (IC50 = 34.03 µg/mL). Moreover, the extract obtained from the flowers of G. gracillima displayed significant aldose reductase inhibition (IC50 = 61.88 µg/mL), as well as O2- and NO scavenging properties. A moderate inhibitory effect was also recorded against pancreatic lipase (IC50 = 362.17 µg/mL) through a mixed inhibition mode. Recorded data supports the potential incorporation of G. gracillima flowers on antidiabetic herbal formulations and/or supplements, with not only straight action on carbohydrates digestion, but also direct interference with targets involved on subsequent diabetes events, such as triglycerides metabolism, inflammation and radical-mediated stress.

Two Kaempferol Glycosides Separated from Camellia Oleifera Meal by High-Speed Countercurrent Chromatography and Their Possible Application for Antioxidation.

Recently, kaempferol and its glycosides have attracted considerable attention owing to their potentially health-benefitting properties including protection against chronic diseases. Here, a microwave-assisted extraction (MAE) method was developed for the extraction of total flavonoid glycosides (FG) from Camellia oleifera meal, a major agrifood waste largely generated as a byproduct from the Camellia oil processing industry. Compared with traditional extraction methods, MAE enables more efficient extraction of FG. High-speed countercurrent chromatography was then applied to separate FG from MAE extract, and two major compounds were successfully separated with purities above 90.0% as determined by HPLC. These two compounds were further identified by UV, FT-IR, ESI-MS, 1 H-NMR, and 13 C-NMR as kaempferol 3-O-[α-L-rhamnopyranosyl-(1→6)-ß-D-glucopyranosyl]-7-O-ß-D-glucopyranoside and kaempferol 3-O-[ß-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl]-7-O-α-L-rhamnopyranoside, which were for the first time separated from C. oleifera meal. The results of antioxidant activity assay demonstrated that both compounds had excellent scavenging activity for DPPH radical, and exhibited protective effects against H2 O2 -induced oxidative damage of vascular endothelial cells. The findings of this work suggest the possibility of employing C. oleifera meal as an attractive source of health-promoting compounds, and at the same time facilitate its high-value reuse and reduction of environmental burden.

Antioxidant Activity of Phenolic Compounds from Fava Bean Sprouts.

Fava beans are eaten all over the world and recently, marketing for their sprouts began in Japan. Fava bean sprouts contain more polyphenols and l-3,4-dihydroxyphenylalanine (l-DOPA) than the bean itself. Our antioxidant screening program has shown that fava bean sprouts also possess a higher antioxidant activity than other commercially available sprouts and mature beans. However, the individual constituents of fava bean sprouts are not entirely known. In the present study, we investigated the phenolic compounds of fava bean sprouts and their antioxidant activity. Air-dried fava bean sprouts were treated with 80% methanol and the extract was partitioned in water with chloroform and ethyl acetate. HPLC analysis had shown that the ethyl acetate-soluble parts contained phenolic compounds, separated by preparative HPLC to yield 5 compounds (1-5). Structural analysis using NMR and MS revealed that the compounds isolated were kaempferol glycosides. All isolated compounds had an α-rhamnose at the C-7 position with different sugars attached at the C-3 position. Compounds 1-5 had ß-galactose, ß-glucose, α-rhamnose, 6-acetyl-ß-galactose and 6-acetyl-ß-glucose, respectively, at the C-3 position. The amount of l-DOPA in fava bean sprouts was determined by the quantitative (1) H NMR technique. The l-DOPA content was 550.45 mg ± 11.34 /100 g of the raw sprouts. The antioxidant activities of compounds 2-5 and l-DOPA were evaluated using the 2,2-diphenyl-1-picrylhydrazyl scavenging assay. l-DOPA showed high antioxidant activity, but the isolated kaempferol glycosides showed weak activity. Therefore, it can be suggested that l-DOPA contributed to the antioxidant activity of fava bean sprouts.

Flavonoid glycosides from Olax mannii: Structure elucidation and effect on the nuclear factor kappa B pathway.

ETHNOPHARMACOLOGICAL RELEVANCE: Olax mannii Oliv. (Olacaceae) is among the many medicinal plants used in Nigeria for the ethnomedicinal management of both cancer and inflammation. Such plants represent potential sources of innovative therapeutic agents for the treatment of cancer and other malignant disorders. While the majority of medicinal plants exert their anticancer effects by direct cytotoxicity on tumor cells, it is important that other mechanisms through which these plants can exhibit anticancer effects are investigated. Preliminary studies indicated that Olax mannii leaves are rich sources of novel flavonoid glycosides. The detailed chemistry as well the mechanisms through which these flavonoid constituents may exert their cancer chemo-preventive and therapeutic effects are, however, not yet investigated. AIM OF THE STUDY: The aim of this study is to carry out a detailed chemical investigation of Olax mannii leaves and the effects of the isolated constituents on the nuclear factor kappa B (NF-κB) pathway. MATERIALS AND METHODS: A methanol leaf extract was subjected to various chromatographic separations to achieve isolation of flavonoid glycosides and the structures of the isolated compounds were elucidated by a combination of 1D and 2D NMR and high resolution mass spectrometry. Biological activities were assessed by measurement of cellular viability and proliferation using quantitative IncuCyte videomicroscopy, trypan blue staining and by quantification of the number of metabolically active K562 cells based on quantitation of ATP. The effect of the compounds on the inhibition of the NF-κB pathway as well as toxicity towards peripheral blood mononuclear cells to evaluate differential toxicity was also assayed. RESULTS: Chemical investigation of the methanol leaf extract of the plant material led to the isolation of three new flavonoid triglycosides, kaempferol 3-O-[α-D-apiofuranosyl-(1 → 2)-α-L-arabinofuranoside]-7-O-α-L-rhamnopyranoside (1), kaempferol 3-O-[ß-D-glucopyranosyl-(1 → 2)-α-L-arabinofuranoside]-7-O-α-L-rhamnopyranoside (2), kaempferol 3-O-[ß-D-arabinopyranosyl-(1→4)-α-L-rhamnopyranoside]-7-O-α-L-rhamnopyranoside (3), in addition to fourteen known flavonoid glycosides (4-17). Of all the tested compounds, only compound 9 (kaempferol 3-O-α-L-rhamnopyranoside) exhibited promising and specific antiproliferative activity on human K562 chronic myelogenous leukemia cells and dose-dependently inhibited NF-κB transactivation. CONCLUSION: The presence of this flavonoid glycoside and derivatives may account for the reported efficacy of Olax mannii leaf extract in the ethnomedicinal management of cancer and inflammation.

Hepatoprotective effects of kaempferol 3-O-rutinoside and kaempferol 3-O-glucoside from Carthamus tinctorius L. on CCl4-induced oxidative liver injury in mice.

Safflower (Carthamus tinctorius L.) is a traditional medicinal and edible herb with a long history of use in China. In this study, a model of hepatotoxicity induced by carbon tetrachloride (CCl4) in mice was used to investigate the hepatoprotective effects of kaempferol 3-O-rutinoside (K-3-R) and kaempferol 3-O-glucoside (K-3-G), two kaempferol glycosides isolated from C. tinctorius L. K-3-R and K-3-G, at doses of 200 mg/kg and 400 mg/kg, were given orally to male mice once/d for 7 days before they received CCl4 intraperitoneally. Our results showed that K-3-R and K-3-G treatment increased the level of total protein (TP) and prevented the CCl4-induced increases in serum aspartate aminotransferase (AST), serum alkaline phosphatase (ALP), and hepatic malondialdehyde (MDA) levels. Additionally, mice treated with K-3-R and K-3-G had significantly restored glutathione (GSH) levels and showed normal catalase (CAT) and superoxide dismutase (SOD) activities, compared to CCl4-treated mice. K-3-R and K-3-G also mitigated the CCl4-induced liver histological alteration, as indicated by histopathological evaluation. These findings demonstrate that K-3-R and K-3-G have protective effects against acute CCl4-induced oxidative liver damage.

Antinociceptive and anti-inflammatory activities of extract and two isolated flavonoids of Carthamus tinctorius L.

ETHNOPHARMACOLOGICAL RELEVANCE: Safflower (Carthamus tinctorius L.) has been long used both in the traditional system and folk medicine as an analgesic anti-inflammatory agent in China. The aim of the study was to evaluate the antinociceptive and anti-inflammatory activities of hydroalcoholic extract (HE) and two isolated kaempferol glycosides of Carthamus tinctorius L. to provide experimental evidence for its traditional use. MATERIALS AND METHODS: Antinociceptive effects of HE, kaempferol 3-O-rutinoside (K-3-R) and kaempferol 3-O-glucoside (K-3-G) were assessed in mice using the acetic acid-induced writhing test, formalin test and cinnamaldehyde test. The anti-inflammatory effects of HE, K-3-R and K-3-G were determined in two animal models: carrageenan-induced paw edema and xylene-induced ear edema. RESULTS: The HPLC analysis showed the presence of K-3-R and K-3-G in Carthamus tinctorius L. HE (500 and 1000mg/kg) as well as K-3-R and K-3-G (150, 300 and 600mg/kg) produced significant inhibition on nociception induced by acetic acid and formalin. Oral treatment of HE, K-3-R and K-3-G at all doses significantly reduced both the nociceptive response and cinnamaldehyde-induced paw edema, effect that was superior to aspirin. In anti-inflammatory tests, HE and K-3-G significantly inhibited the paw edema during the both phases of carrageenan-induced inflammation while K-3-G suppressed the late phase inflammation only. HE (400 and 800mg/kg) and K-3-G (200, 400, 800mg/kg) produced significant dose-dependent inhibition of xylene-induced ear edema development. K-3-R only suppressed ear edema formation at a high dose (800mg/kg). CONCLUSIONS: These results demonstrate that Carthamus tinctorius L. extract possess remarkable antinociceptive and anti-inflammatory activities which may be due to K-3-R and K-3-G at least in part, supporting the folkloric usage of the plant to treat various inflammatory and pain diseases.

Low and moderate photosynthetically active radiation affects the flavonol glycosides and hydroxycinnamic acid derivatives in kale (Brassica oleracea var. sabellica) dependent on two low temperatures.

Kale (Brassica oleracea var. sabellica) contains a large number of naturally occurring structurally different non-acylated and acylated flavonol glycosides as well as hydroxycinnamic acid derivatives. The objective of this study was to determine the effect of low and moderate photosynthetic active radiation (PAR) and how these levels interact with low temperature in these phenolic compounds. Juvenile kale plants were treated with PAR levels from 200 to 800 µmol m(-2) s(-1) at 5 and 10 °C under defined conditions in climate chambers. Of the investigated 20 compounds, 11 and 17 compounds were influenced by PAR and temperature, respectively. In addition, an interaction between PAR and temperature was found for eight compounds. The response of the phenolic compounds to PAR was structure-dependent. While quercetin triglycosides increased with higher PAR at 5 and 10 °C, the kaempferol triglycosides exhibited the highest concentrations at 400 µmol m(-2) s(-1). In contrast, kaempferol diglycosides exhibited the highest concentrations at increased PAR levels of 600 and 800 µmol m(-2) s(-1) at 10 °C. However, key genes of flavonol biosynthesis were influenced by temperature but remained unaffected by PAR. Furthermore, there was no interaction between the PAR level and the low temperature in the response of hydroxycinnamic acid derivatives in kale with the exception of caffeoylquinic acid, which decreased with higher PAR levels of 600 and 800 µmol m(-2) s(-1) and at a lower temperature. In conclusion, PAR and its interaction with temperature could be a suitable tool for modifying the profile of phenolic compounds.

Flavonol glycosides found in hydroethanolic extracts from Tilia cordata, a species utilized as anxiolytics / Flavonóides glicosídeos encontrados no extrato hidroalcoólico de Tilia cordata, espécie usada como ansiolítico

Tilia species, among which is Tilia cordata Mill. (Tiliaceae), have been used in folk medicine as anxiolytic. The hydroethanolic extract was analyzed by using liquid chromatography with mass spectrometry HPLC-DAD-ESI-MS/MS in negative ion mode, and its chemical composition was compared to flavonoids reported as anxiolytics. The major flavonoids found were: quercetin-3,7-di-O-rhamnoside, kaempferol-3,7-di-O-rhamnoside and kaempferol 3-O-(6"-p-coumaroyl glucoside) or tiliroside. The anxiolytic activity of the genus Tilia has been attributed to the presence of quercetin and kaempferol derivatives, while the anxiolytic activity of T. americana var. Mexicana was attributed to tiliroside, which was also found among the major constituents of this species.

As espécies de Tilia, entre elas, a Tilia cordata Mill. (Tiliaceae) são utilizadas como ansiolíticas na medicina popular. O extrato hidroalcoólico foi analisado usando cromatografia líquida acoplada à espectrometria de massas HPLC-DAD-ESI/MS/MS no modo negativo e a sua composição química foi comparada com os flavonóides já reportados como ansiolíticos. Os principais flavonóides encontrados foram: quercetina-3,7-di-O-rhamnosideo, canferol-3,7-di-O-rhamnosideo, e canferol 3-O-(6"-p-cumaroil glucosideo) ou tilirosideo. A atividade ansiolítica do gênero Tília tem sido atribuída à presença de derivados de canferol e quercetina, enquanto que a atividade ansiolítica da T. americana var. Mexicana foi atribuída ao tilirosideo, o qual também foi encontrado entre os principais constituintes desta espécie.