Chemical constituents and antifungal potential of Attalea geraensis Barb. Rodr. (Arecaceae) palm leaves, a species native to the Cerrado of Brazil.

Fungal diseases, especially those that affect the root systems of plants, caused by Rhizoctonia and Macrophomina are limiting factors for achieving high crop yields. Alternatives to controlling fungi with chemical products drive the search for new options for bioactive compounds from plants. Attalea geraensis, a palm tree from the Brazilian Cerrado, is rich in flavonoids with antifungal actions. The objective of this work is to identify the chemical classes present in the ethanolic extract of green leaves of A. geraensis and determine the antifungal potential of the extract against isolates of Macrophomina phaseolina (Tassi) Goid. and Rhizoctonia solani JG Kühn. Phytochemical prospection, flavonoid dereplication, and antifungal activity were carried out of the ethanolic extract of the green leaves of A. geraensis harvested in the Cerrado area of Brazil. Steroids, triterpenes, saponins, and anthraquinones are described here for the first time for the leaves of A. geraensis. The flavonoids quercetin, isorhamnetin, 3,7-dimethylquercetin, quercetin 3-galactoside, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one, rhamnazin 3-galactoside, keioside, and rhamnazin 3-rutinoside were identified. Of these, only quercetin and isorhamnetin had already been identified in the leaves of A. geraensis. The results show a fungistatic potential for the species. The diversity of flavonoids present in the leaves of A. geraensis may be the result of a synergistic action between fungus and plant or there could be an antagonistic effect between flavonoids and the other identified chemical classes.

Screening and identification of bioactive components resistant to metallo-beta-lactamase from Schisandra chinensis (Turcz.) Baill. by metalloenzyme-immobilized affinity chromatography.

The screening and identification of bioactive components, which are effectively resistant to metallo-beta-lactamase (MßL), were studied in the alcohol extract of Schisandra chinensis (Turcz.) Baill. by metalloenzyme-immobilized affinity chromatography. Taking bizinc metalloenzyme beta-lactamase II from Bacillus cereus (Bc II) and monozinc metalloenzyme CphA from aeromonas hydrophila (CphA) as examples, we studied the feasibility of this scheme based on the construction of metalloenzyme-immobilized chromatographic model. It was found that the Bc II- and CphA-immobilized chromatographic column could be used not only to explore the interaction between the MßL and their specific ligands, but also to screen the bioactive components from traditional Chinese medicine. The Bc II-and CphA-immobilized columns were used to screen the bioactive components from the alcohol extract of Schisandra chinensis (Turcz.) Baill. Time-of-flight tandem mass spectrometry analysis and molecular docking revealed that isobutyl 3-O-sulfo-ß-D-galactopyranoside is the effective bioactive components that could bind with metalloenzyme Bc II. It is believed that our current work may provide a methodological reference for screening MßL inhibitors from traditional Chinese medicine.

Method Development and Validation for Simultaneous Determination of Six Flavonoids in Rat Eyes after Oral Administration of Diospyros kaki Leaves Extract by UPLC-MS/MS.

A robust ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) technique was proven effective for simultaneous characterization of six flavonoids including quercetin-3-O-beta-galactoside (Q3GAL), quercetin-3-O-beta-glucoside (Q3GLU), quercetin-3-(2-galloylglucoside) (Q3GG), kaempferol-3-O-beta-galactoside (K3GAL), kaempferol-3-O-beta-glucoside (K3GLU), and kaempferol-3-(2-galloylglucoside) (K3GG) in rat eyes. By investigation of corresponding validation parameters (linearity, selectivity, precision, accuracy, matrix effect, extraction recovery, and stability), the method was verified to be within current acceptable criteria. Thereafter, the validated method enabled quantification of the six compounds successful in rat eyes after oral administration of ethanol extract Diospyros kaki (EEDK) at 0, 3, 15, 35, 60, 120 min.

Consumption evaluation of one apple flesh a day in the initial phases prior to adenoma/adenocarcinoma in an azoxymethane rat colon carcinogenesis model.

Colorectal cancer (CRC) is the fourth cancer with the most new cases reported in 2018 worldwide. Consumption of fruit and vegetables is a protective factor against the risk of CRC. Beyond this, flavonoids could orchestrate these healthy effects. Apart from containing the typical apple flavonoids, red-fleshed apples also contain anthocyanins, mainly cyanidin-3-O-galactoside (Cy3Gal). Through an azoxymethane rat carcinogenesis model, a study was carried out in order to assess the possible protective effects of apple polyphenols, with special attention to anthocyanins. In addition, apart from negative and positive controls, a group with chemotherapy with 5-fluorouracil (5FU) was included to compare their performance against the output collected from the animal treatments with white-fleshed apple (WF), red-fleshed apple (RF) and Cy3Gal (AE). Although the 5FU group presented the best performance towards aberrant crypt foci (ACF) inhibition (70.1%), rats fed with white-fleshed apples ('Golden Smoothee') were able to achieve 41.3% ACF inhibition, while none of the challenged treatments (WF, RF and AE) suffered mucin depletion in their colonocytes. Expression changes of 17 genes related to CRC were assessed. In detail, the ACF inhibition phenotype detected in 5FU and WF groups could be explained through the expression changes detected in the apoptosis-related genes of Aurka, p53 and Cox2. Moreover, in the apple consumption groups (WF and RF), a reduced protein expression of matrix metalloproteinases with gelatinase activity (MMP-2 and 9) was detected. Overall, our study suggests an effect of apple polyphenols and apple anthocyanin Cy3Gal against colon carcinogenesis, retarding/diminishing the appearance of the precancerous markers studied.

Isolation and Identification of Anthocyanin Component in the Fruits of Acanthopanax Sessiliflorus (Rupr. & Maxim.) Seem. by Means of High Speed Counter Current Chromatography and Evaluation of Its Antioxidant Activity.

Acanthopanax sessiliflorus (Rupr. & Maxim.) Seem. (Araliaceae) is one of the most abundant species of genus Acanthopanax. The fruits of A. sessiliflorus are used in traditional medical protocols as an analgesic, tonic, antidiabetic, antihypertensive, anti-inflammatory, antitumor, and immune-stimulating agent. In this work, we carried out a comprehensive investigation into the anthocyanin components in the fruits of A. sessiliflorus. The anthocyanin content in the fresh fruits of A. sessiliflorus was determined by high performance liquid chromatography-diode array detection (HPLC/DAD), and the anthocyanin component was isolated from these using high-speed counter-current chromatography (HSCCC) and elucidated by electro-spray ionization-mass spectrometry (ESI/MS), 1H- and 13C-NMR. Its antioxidant activity was evaluated by ferric-reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH). We found that A. sessiliflorus contained a gross anthocyanin content of 121.35 mg/100 g. HSCCC was successfully used for separation and purification of the primary anthocyanin component, cyanidin 3-xylosyl-galactoside. The antioxidant and radical scavenging tests indicated that cyanidin 3-xylosyl-galactoside is a potent antioxidant.

Phytochemical Profiles of New Red-Fleshed Apple Varieties Compared with Traditional and New White-Fleshed Varieties.

This study is an exhaustive chemical characterization of the phenolic compounds, triterpenes, and organic and ascorbic acids in red-fleshed apple varieties obtained by different breeding programs and using five traditional and new white-fleshed apple cultivars as reference. To carry out these analyses, solid-liquid extraction (SLE) and ultraperformance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS) were used. The results showed that the red-fleshed apples contained, in either the flesh or peel, higher amounts of phenolic acids (chlorogenic acid), anthocyanins (cyanidin-3-O-galactoside), dihydrochalcones (phloretin xylosyl glucoside), and organic acids (malic acid) but a lower amount of flavan-3-ols than the white-fleshed apples. These quantitative differences could be related to an up-regulation of anthocyanins, dihydrochalcones, and malic acid and a down-regulation of flavan-3-ols (anthocyanin precursors) in both the flesh and peel of the red-fleshed apple varieties. The reported results should be considered preliminary because the complete phytochemical characterization of the red-fleshed apple cultivars will be extended to consecutive harvest seasons.

The identification and evaluation of two different color variations of tea.

BACKGROUND: The tea plant, Camellia sinensis (L.) O. Kuntz, is a perennial woody plant widely cultivated for the production of a popular non-alcoholic beverage. To rapidly identify and evaluate two different color tea varieties (yellowish and purplish), the main phenotypic traits and quality components were tested in the present study. The metabolic profiles of tea shoots and leaves were also analyzed using liquid chromatography-tandem mass spectrometry. RESULTS: The yellowish variation had a higher active level with respect to metabolism of catechins, and the contents of luteolin and kaempferol 3-α-d-glucoside were much higher compared to in the other variations. However, the purplish variation had a low content of theanine and a high content of caffeine. The contents of quercetin and kaempferol 3-α-d-galactoside were highest in purplish leaves. Moreover, the yellowish variation had the highest total quality scores for green teas and black teas, whereas the purplish variation had the highest scores for oolong teas. CONCLUSION: Both the yellowish variation and the purplish variation represent excellent breeding materials and are worthy of breeding as new tea cultivars. The yellowish variation is more suitable for making high-grade green teas or black teas, whereas the purplish variation is suitable for producing fine quality oolong teas. © 2016 Society of Chemical Industry.

Effects of pretreatments on anthocyanin composition, phenolics contents and antioxidant capacities during fermentation of hawthorn (Crataegus pinnatifida) drink.

The effect of microwave and heat pretreatment on the content and composition of anthocyanins, phenolics, and the antioxidant capacity of hawthorn drink were studied. Nine anthocyanins were isolated by chromatographic separation from the Zirou hawthorn source and their structure identified using HPLC-DAD-ESI/MS analysis. Heat and microwave pretreatments had a significant impact on the relative contents of hawthorn anthocyanins, such as cyanidin-3-galactoside (82.9% and 76.9%, respectively) and cyanidin-3-glucoside (9.2% and 11.5%, respectively). Pretreatment had no significant effect on pH, total soluble solid or total acid. More anthocyanins remained after heat treatment than after microwaving (0.745mg/100mL), and were 52.4% higher than the control group after storage for 7days. The colour density of the heat treated group was higher than the control group (24.5%) after 12days of fermentation. The main antioxidant capacities of the hawthorn drinks came from total polyphenolics rather than total anthocyanins or total flavonoids.

Phenolic compounds and bioactivities of pigmented rice.

The pigmented rice has been consumed in China, Japan, and Korea for a long time. It has been used for strengthening kidney function, treating anemia, promoting blood circulation, removing blood stasis, treating diabetes, and ameliorating sight in traditional Chinese medicine. The extracts from pigmented rice are used as natural food colorants in bread, ice cream, and liquor as well as functional food. The pigmented rice is mainly black, red, and dark purple rice, and contains a variety of flavones, tannin, phenolics, sterols, tocols, γ-oryzanols, amino acids, and essential oils. Anthocyanins are thought as major functional components of pigmented rice. Several anthocyanins have been isolated and identified from the pigmented rice, including cyanidin 3-glucoside, cyanidin 3-galactoside, cyanidin 3-rutinoside, cyanidin 3,5-diglucoside, malvidin 3-galactoside, peonidin 3-glucoside, and pelargonidin 3,5-diglucoside. This review provides up-to-date coverage of pigmented rice in regard to bioactive constituents, extraction and analytical methods, and bioactivities. Special attention is paid to the bioactivities including antioxidant and free radical scavenging, antitumor, antiatherosclerosis, hypoglycemic, and antiallergic activities.

Antioxidant activities and major anthocyanins of Myrobalan plum (Prunus cerasifera Ehrh.).

UNLABELLED: Total phenolic content, total antioxidant activity of Myrobalan plum (Prunus cerasifera Ehrh.) and anthocyanin content in peel were analyzed in this article. In addition, ultra-performance liquid chromatography with photodiode array detection and electrospray ionization tandem mass spectrometry were used to determine anthocyanin composition of this fruit. The range of total phenolic content of the tested samples was 1.34 to 6.11 g/kg fresh weight (FW), and anthocyanin content in fruit peel of Myrobalan plum was from 1.93 to 19.86 g/kg peel. Ferric reducing antioxidant power values varied from 11.20 to 44.83 µmol Trolox equivalent/g FW. Four main kinds of anthocyanins in purple Myrobalan plum were detected while 6 kinds in red ones. PRACTICAL APPLICATION: The article showed the anthocyanin composition, phenolic content, and antioxidant activities of wild Myrobalan plum. The purple Myrobalan plum could be developed as a resource of fruit drinks because of its high antioxidant activity and the peel could be used as the resource to extract natural pigments.

Evaluation of the biochemical components and chromatic properties of the juice of Vaccinium macrocarpon Aiton and Vaccinium oxycoccos L.

Benzoic acid, total anthocyanins, soluble solids, titratable acidity, and colour properties in juice of the American cranberry Vaccinium macrocarpon and the European cranberry Vaccinium oxycoccos were investigated. Berry juices of V. macrocarpon cultivars were distinguished by their higher total anthocyanin and benzoic acid amounts. These cultivars accumulated on average 43.11 mg/l of benzoic acid and 92.45 mg/l of total anthocyanins. The levels of benzoic acid and total anthocyanins in V. oxycoccos cultivars were 17.52 mg/l and 42.54 mg/l, respectively. The V. macrocarpon cultivars 'Franklin', 'Le Munyon', 'Searles', and 'Early Richard' were selected as the best according to the enhanced total anthocyanins and benzoic acid amounts. The separation of anthocyanins by HPLC-UV-VIS revealed the presence of six anthocyanins, with peonidin-3-galactoside being the most prevalent. Galactoside together with glucoside conjugates comprised the largest percentage of total anthocyanins in the juices of V. macrocarpon and V. oxycoccos cultivars.

[A new C-glycosylflavone from Peperomia dindygulensis].

OBJECTIVE: To study the chemical constituents of Peperomia dindygulensis. METHOD: Several column chromatographic methods were used to isolated compounds from P. dindygulensis and spectroscopic methods (1H-NMR, 13C-NMR, HMQC, HMBC, 1D- HOHAHA, NOE) were used to identify the structures of isolated compounds. RESULT: Compound 1 was isolated and identified as 2"-O-beta-D-galactosylisoswertisin. CONCLUSION: Compound 1 was a new compound.

Fermented pigeon pea (Cajanus cajan) ingredients in pasta products.

Pigeon pea (Cajanus cajan var. aroíto) seeds were fermented in order to remove antinutritional factors and to obtain functional legume flour to be used as pasta ingredients. Fermentation brought about a drastic reduction of alpha-galactosides (82%), phytic acid (48%), and trypsin inhibitor activity (39%). Fermented legume flours presented a notable increase of fat and total soluble available carbohydrates, a slight decrease of protein, dietary fiber, calcium, vitamin B2, vitamin E, and total antioxidant capacity, and a decrease of soluble dietary fiber, Na, K, Mg, and Zn contents. No changes were observed in the level of starch and tannins as a consequence of fermentation. The fermented flour was used as an ingredient to make pasta products in a proportion of 5, 10, and 12%. The supplemented pasta products obtained had longer cooking times, higher cooking water absorptions, higher cooking loss, and higher protein loss in water than control pasta (100% semolina). From sensory evaluations, fortified pasta with 5 and 10% fermented pigeon pea flour had an acceptability score similar to control pasta. Pasta supplemented with 10% fermented pigeon pea flour presented higher levels of protein, fat, dietary fiber, mineral, vitamin E, and Trolox equivalent antioxidant capacity than 100% semolina pasta and similar vitamins B1 and B2 contents. Protein efficiency ratios and true protein digestibility improved (73 and 6%, respectively) after supplementation with 10% fermented pigeon pea flour; therefore, the nutritional value was enhanced.

Nutritional potential of raw and free alpha-galactosides lupin (Lupinus albus Var. multolupa) seed flours. Effect of phytase treatment on nitrogen and mineral dialyzability.

The effect of the removal of alpha-galactosides from Lupinus albus L. var. multolupa on the chemical composition of the prepared flour and the dialyzability of N, total P, Ca, Mg, Fe, Zn, and Mn was studied. The extraction process caused a significant increase in total and insoluble nitrogen contents and decreased the amount of soluble protein nitrogen. However, neither these changes nor treatment with phytase seemed to considerably affect in vitro protein digestibility. Except for Ca and Cu, total mineral contents were significantly reduced by the extraction process. The process also caused a significant reduction in the dialyzability of all the minerals studied except P. The decrease in mineral dialyzability was partially counteracted by phytase treatment in amounts of 250-500 phytase units/kg of lupin flour. In the case of Fe, mineral dialyzability did not differ significantly between the two lupin flours studied with treatment with 500 phytase units/kg. Zinc dialyzability was the most efficiently improved by phytase treatment (P < 0.0001), followed by P, Fe, and Mn, and finally by Ca and Mg (P < 0.05).

Novel NMR platform for detecting gene transfection: synthesis and evaluation of fluorinated phenyl beta-D-galactosides with potential application for assessing LacZ gene expression.

Gene therapy holds great promise for the treatment of diverse diseases, but widespread implementation is hindered by difficulties in assessing the success of transfection. The development of noninvasive reporter techniques based on appropriate molecules and imaging modalities may help to assay gene expression. Fluorophenyl-beta-d-galactopyranosides provide a novel class of NMR active molecules, which are highly responsive to the action of beta-galactosidase (beta-gal), the product of the lacZ gene. The reporter molecules are stable in solution and with respect to wild-type cells, but the enzyme causes liberation of the aglycon, a fluorophenol, accompanied by distinct color formation and a (19)F NMR chemical shift of 5-10 ppm, depending on pH. Synthetic strategy, experimental methods, and molecular and (19)F NMR characteristics are reported for a series of molecules in solution, blood, and tumor cells. This class of molecules presents a new strategy for assaying gene expression with a highly versatile molecular structural platform.

Nutritional evaluation of pea (Pisum sativum L.) protein diets after mild hydrothermal treatment and with and without added phytase.

The effect of mild hydrothermal treatment and the addition of phytase under optimal conditions (pH 5.5, 37 degrees C) on the nutritive utilization of the protein of pea (Pisum sativum L.) flour was studied in growing rats by examining the chemical and biological balance. Mild hydrothermal treatment produced reductions of 83, 78, and 72%, respectively, in the levels of alpha-galactosides, phytic acid, and trypsin inhibitors and also produced a significant increase in the digestive utilization of protein. The additional fall in the levels of phytic acid caused by the addition of phytase did not lead to a subsequent improvement in the digestive utilization of protein. The mild hydrothermal treatment of pea flour produced a significant increase in the metabolic utilization of protein and carbohydrates, which was reflected in the protein efficiency ratio and food transformation growth indices. These effects were not observed in the phytase-supplemented pea diet.

Carbohydrate fractions of legumes: uses in human nutrition and potential for health.

Starch and fibre can be extracted, using wet or dry processes, from a variety of grain legumes and used as ingredients for food. alpha-Galactosides can be isolated during wet processes from the soluble extract. Starch isolates or concentrates are mostly produced from peas, whereas dietary fibre fractions from peas and soyabean are commercially available. The physico-chemical characteristics of fibre fractions very much depend on their origin, outer fibres being very cellulosic whereas inner fibres contain a majority of pectic substances. Inner fibres are often used as texturing agents whereas outer fibres find their main uses in bakery and extruded products, where they can be introduced to increase the fibre content of the food. Most investigations on impacts on health have been performed on soyabean fibres. When positive observations were made on lipaemia, glucose tolerance or faecal excretion, they were unfortunately often obtained after non-realistic daily doses of fibres. Legume starches contain a higher amount of amylose than most cereal or tuber starches. This confers these starches a lower bioavailability than that of most starches, when raw or retrograded. Their low glycaemic index can be considered as beneficial for health and especially for the prevention of diseases related to insulin resistance. When partly retrograded, these starches can provide significant amount of butyrate to the colonic epithelium and may help in colon cancer prevention. alpha-Galactosides are usually considered as responsible for flatus but their apparent prebiotic effects may be an opportunity to valorize these oligosaccharides.

Effect of soaking, cooking and germination on the oligosaccharide content of selected Nigerian legume seeds.

The identity and quantity of and effect of processing on raffinose oligosaccharides in raw, mature seeds of lima beans (Phaseolus lunatus), pigeon peas (Cajanus cajan), African yam beans (Sphenostylis sternocarpa) and jackbeans (Canavalia ensiformis) were investigated. Sucrose, raffinose, stachyose and verbascose were identified by HPLC in all the legume seeds. The total alpha-galactoside contents of the seeds in decreasing order were African yam beans 3.84 mg/100 mg; white lima beans 3.62 mg/100 mg; cream pigeon peas 3.51 mg/100 mg; red lima beans 3.37 mg/100 mg; jackbeans 2.83 mg/100 mg and brown pigeon peas 2.34 mg/100 mg. The predominant oligosaccharide was verbascose in pigeon peas and stachyose in the other three legumes. Cooking unsoaked seeds brought about a greater reduction in the total alpha-galactoside content than soaking for nine hours. The removal of oligosaccharides was higher in legumes cooked in alkaline solution than in water. Germination quantitatively reduced raffinose, stachyose and verbascose while sucrose was increased in all seeds except red lima beans and jackbeans.

Anti-nutritional constituents of six underutilized legumes grown in Nigeria.

Six underutilized legume seeds grown in Nigeria namely, red and white lima beans, brown and cream pigeon pea, African yam bean and jackbean were analysed for different anti-nutritional factors Sojasapogenol B was identified as the predominant sapogenol in lima beans and jackbeans by capillary gas chromatography. The content of total inositol phosphates and individual inositol phosphates (IP6, IP5, IP4 and IP3) were analysed by ion-pair HPLC, being in the range of other legumes. Trace quantities of lupanine were identified as the alkaloid in jackbean. alpha-Galactosides were present in all the legume seeds, stachyose being the predominant galactoside in lima beans, African yam bean and jackbean, and verbascose in pigeon pea. The haemagglutinating activity was estimated as a measure of the lectin content of the samples. African yam bean was found to have the highest heamagglutinating activity. Tannins were found to be in low quantities. The presence of these anti-nutrients in relation to the nutritional value of the legume is discussed.

Antinutritional factors in anasazi and other pinto beans (Phaseolus vulgaris L.).

Antinutritional factors of anasazi bean were compared to traditional pinto bean (Phaseolus vulgaris L.). Anasazi beans contained less (p<0.001) soluble and bound condensed tannins compared to pinto beans. No differences (p>0.05) in stachyose and raffinose content were found between the two bean types; verbascose was not detected at all. Significant (p<0.05) differences in lectin content were observed between anasazi and pinto bean. The lectins of anasazi beans were classified as non toxic and those of the pinto beans as toxic types. No differences (p>0.05) in inhibitor activity against human and bovine trypsin and chymotrypsin were found between the two bean types.