Development of a high performance thin layer chromatography method for the rapid qualification and quantification of phenolic compounds and abscisic acid in honeys
Honey is a natural product with a complex chemical composition consisting of sugars and other bioactive compounds. It is important in many traditional systems of medicine, exhibiting interesting bioactivities, in particular antimicrobial, anti-inflammatory and antioxidant effects. Authentication of botanical origin of honeys is particularly important in this context. Therefore, methods for quality control of honey and detection of its adulteration are very important. A HPTLC method for the quantitative determination of phenolic compounds in honey was developed for the first time. Seven phenolic compounds were detected and determined quantitatively in lime and acacia honey samples. The obtai…
Pholiotina cyanopus, a rare fungus producing psychoactive tryptamines
Abstract Pholiotina cyanopus was collected from wood chips and other woody remnants of undetermined tree species. Its basidiomata were found in June within the area of closed sawmill in the central part of Żywiec city (SW Poland). Description and illustration of Ph. cyanopus based on Polish specimens are provided and its ecology, general distribution and comparison with similar taxa – Pholiotina smithii, Pholiotina sulcatipes, and others are discussed as well. The identity of the active compounds of Ph. cyanopus was additionally determined. Liquid chromatography–mass spectrometry (LC-MS) data sets were obtained to support the occurrence of psilocybin and its analogues – psilocin, baeocystin…
Chemometrics as a Tool of Origin Determination of Polish Monofloral and Multifloral Honeys
The aim of this study was to evaluate the application of chemometrics studies to determine the botanical origin of Polish monofloral honeys using NMR spectroscopy. Aqueous extracts of six kinds of honeys, namely, heather (Calluna vulgaris L.), buckwheat (Fagopyrum esculentum L), lime (Tilia L), rape (Brassica napus L. var. napus), acacia (Acacia Mill.), and multifloral ones, were analyzed. Multivariate chemometric data analysis was performed using principal component analysis (PCA) and orthogonal partial least-squares discriminant analysis (OPLS-DA). Chemometric analysis supported by pollen analysis revealed the incorrect classification of acacia honeys by the producers. Characteristic moti…
Chromatographic fingerprint, antioxidant activity, and colour characteristic of polish goldenrod (Solidago virgaurea L.) honey and flower
In recent times, the nutraceutical and pharmaceutical interest in honey due to its well-known health properties has increased. Consumers need clear and precise information, so that they can make informed choices about their diet and the foods they buy. Therefore, gas chromatography–mass spectrometry (GC–MS) and high-performance liquid chromatography with a photodiode array detector (HPLC-PAD) was revealed a general characteristic fingerprint of polish monofloral goldenrod honey and flowers. In addition, high-performance thin-layer chromatography (HPTLC) has proven to be a useful tool for determining similarity patterns of common bands among honey from the same floral source and thus can be …
Authentication of phacelia honeys (Phacelia tanacetifolia) based on a combination of HPLC and HPTLC analyses as well as spectrophotometric measurements
Abstract The growing interest in the quality of honey affects customer preferences and consumption trends. Generally, monofloral honeys are more expensive than multifloral honeys, and the price strictly depends on its botanical origin. The increasing popularity of a variety of monofloral brands has led to the increasing number of adulterations and therefore for the need to develop new analytical methods for assessing honey authenticity. The purpose of the present study was to develop a method for the authentication of phacelia honeys on the basis of HPLC and HPTLC analyses and spectrophotometry. The results obtained by spectrophotometric analysis indicated significant differences only betwe…
HPTLC Phenolic Profiles as Useful Tools for the Authentication of Honey
The present study reveals the utility of high-performance thin-layer chromatographic (HPTLC) fingerprinting of phenolic constituents for the authentication of monofloral honeys. The obtained data enables a more complete assessment of honey quality and the identification of emerging threats to honey quality. The developed procedure facilitates differentiation of varietal honeys and detection of honey adulterations. We used an HPTLC fingerprint analysis to determine the characteristic patterns of different honey types (willow, buckwheat, heather, pine honeydew, and manuka honey). The HPTLC chromatograms were used to determine the differences in the botanical origin of the honey samples on the…
The chemical composition of the floral extract of Epipogium Aphyllum sw. (Orchidaceae): A cluefor thier pollination biology
Epipogium aphyllum is a rare European obligate mycoheterotrophic orchid lacking chlorophyll. It has not been studied previously with respect to pollination biology. We studied the association between the composition of floral scent emission and its pollination systems. Field observation indicates that the main pollinators of Epipogium aphyllum are representatives of the genus Bombus (Hymenoptera), B. lucorum, B. hortorum, B. terrestris, B. pascuorum and B. proteus, and the genus Apis (Hymenoptera) namely A. mellifera. The main potential vector (observed to accidentally carry pollen), is most likely Episyrphus balteatus (Diptera, Syrphidae). The chemical composition of the floral extracts of…
HPTLC fingerprinting—rapid method for the differentiation of honeys of different botanical origin based on the composition of the lipophilic fractions
Bee honey possess various nutritional and medicinal functions, which are the result of its diverse chemical composition. The numerous bioactive compounds in honey come from flower nectar
Possible Fungistatic Implications of Betulin Presence in Betulaceae Plants and their Hymenochaetaceae Parasitic Fungi
Betulin and its derivatives (especially betulinic acid) are known to possess very interesting prospects for their application in medicine, cosmetics and as bioactive agents in pharmaceutical industry. Usually betulin is obtained by extraction from the outer layer of a birch bark. In this work we describe a simple method of betulin isolation from bark of various species of Betulaceae trees and parasitic Hymenochaetaceae fungi associated with these trees. The composition of the extracts was studied by GC-MS, whereas the structures of the isolated compounds were confirmed by FTIR and 1H NMR. Additionally, the significant fungistatic activity of betulin towards some fi lamentous fungi was deter…
Chromatographic Profiles of the main Secondary Metabolites in the Monarda fistulosa L. Aerial Part
Two different methods of chromatographic analysis have been used in this study for the phytochemical evaluation of main secondary metabolites in the aerial part of bee balm (Monarda fistulosa L.) as the non-officinal medicinal plant of the Lamiaceae Martinov family. The high performance thin layer chromatography (HPTLC) fingerprinting method was developed for the qualitative analyses of phenolic and non-polar compounds in the bee balm herb after its maceration in the solvents of different polarity. Such polyphenols as rosmarinic, caffeic and chlorogenic acids were authentically identified in the methanol extract of herb using HPTLC. Aromatic monoterpenoid thymol was identified by the HPTLC …
Phytochemical and Pharmacological Evaluation of the Residue By-Product Developed from the Ocimum americanum (Lamiaceae) Postdistillation Waste
The yield of essential oils in plants is not high and postdistillation wastes rich in phenolic compounds could be used to enhance the profitability of essential oil-bearing plants. The aim of the study was to evaluate polyphenols in a dry extract obtained from the postdistillation waste of the American basil (Ocimum americanum L.) herb, and to conduct the screening of its pharmacological activities. Rosmarinic acid, caffeic acid and rutin were identified in the extract using high-performance thin-layer chromatography. The high-performance liquid chromatography analysis found the presence of a plethora of polyphenols in the extract. Rosmarinic acid, luteolin-7-O-glucoside and rutin were as t…
Chemical Profiling of Polyfloral Belgian Honey: Ellagic Acid and Pinocembrin as Antioxidants and Chemical Markers
Chemical profiling of northern Belgian polyfloral honeys was performed to analyse their phenolic compound content (flavonoids and phenolic acids). First, samples were subjected to a standard analysis of their physicochemical properties, and then, the phenolic fraction was isolated and analysed using a HPLC/PAD method. All of the tested honeys showed a common and specific phenolic profile that could be the basis for the differentiation of polyfloral honeys of the Antwerp region from other polyfloral honeys. Chromatographic data indicated a high content of ellagic acid (9.13–13.66 mg/100 g honey), as well as the flavonoid pinocembrin (1.60–1.85 mg/100 g honey) in these honeys. Ellagic acid, a…
Development of high-performance thin layer chromatography method for identification of phenolic compounds and quantification of rosmarinic acid content in some species of the Lamiaceae family
ABSTRACT Aim: Representatives of Nepetoideae Burnett subfamily are promising species of the Lamiaceae Martinov family because of accumulating such valuable groups of secondary metabolites as terpenoids and polyphenols. A high-performance thin layer chromatography (HPTLC) fingerprint method for the qualitative determination of phenolic compounds and for the quantification of rosmarinic acid (RA) content in methanol extracts of five species of this subfamily was developed for the first time. Materials and Methods: Dried aerial parts of Dracocephalum moldavica L., Ocimum americanum L., Lophanthus anisatus (Nutt.) Benth., Monarda fistulosa L., and Satureja hortensis L. collected in flowering pe…
Rapid determination of ibotenic acid and muscimol in human urine
Phosphorus Profile of Basidiomycetes
Phosphorus profiles of methanolic extracts of dried basidocarps of edible and toxic mushrooms collected in Poland have been determined. Despite of the presence of standard phosphorus compounds majority of the extracts revealed the presence of phosphonates. Also, the presence of polyphospates was determined in selected cases.
An adventive Panaeolus antillarum in Poland (Basidiomycota, Agaricales) with notes on its taxonomy, geographical distribution, and ecology
Abstract Coprophilous fungus, Panaeolus antillarum rarely recorded in Europe, is reported here for the first time from the Augustow Plane, north-eastern Poland. This thermophilic species was found outdoors in August on horse dung mixed with straw. A chemical analysis did not confirm the presence of the psychoactive alkaloids in collected material. A complete description and illustration of the species based on Polish specimens are presented and notes on its taxonomy, ecology, world distribution and comparison with similar taxa — P. semiovatus var. semiovatus, P. semiovatus var. phalaenarum, and others are also provided.
Sedative Effect and Standardization Parameters of Herbal Medicinal Product Obtained from the Ocimum americanum L. Herb
Abstract Sedative phytomedications continue to play an important role in the management of a considerable amount of anxiety symptoms because of the various side effects of synthetic sedatives and tranquilizers. However, developing new herbal drugs needs their appropriate quality control according to the relevant requirements. The aim of the study was to determine the sedative properties of the tinctures obtained from the American basil (Ocimum americanum L., Lamiaceae Martinov family) herb and to develop the standardization parameters for the promising herbal medicinal product. The open field test was used to evaluate the sedative effect of the prepared tinctures: (1) with the added of O. a…
Antioxidant Phenolic Compounds in Salvia officinalis L. and Salvia sclarea L.
Abstract The differences in the chemical composition of the phenolic compounds of Salvia officinalis versus Salvia sclarea growing in different habitats, were studied. First, the optimal solvent - methanol - for ultrasonic extraction of phenolic compounds from these plants was chosen experimentally. Total phenolic content and 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays were determined spectrophotometrically. Total phenolic content was in the range of 63.9 to 134.4 mg GAE/g of plant depending on the studied species. The highest antiradical activity was displayed by the methanol fractions of S. sclarea varieties (83 and 67%). HPLC-DAD analysis of extracts was done in order to identify the pre…
Herbicidal Derivatives of Aminomethylenebisphosphonic Acid. Part IV. Hydroxyalkylidenebisphosphonates, Iminomethylenebisphosphonates and Ureidomethylenebisphosphonates
Derivatives of aminomethylenebisphosphonic acids constitute a class of promising herbicides. Replacement of the amino group by hydroxyl, ureido, thioureido, or imino moieties leads to compounds of significant herbicidal properties. This indicates that protonated amino function is not a requirement for phytotoxic action of bisphosphonates.
Secondary metabolites from the aerial parts of Cytisus villosus Pourr
Phytochemical investigation of the aerial parts of Cytisus villosus Pourr. resulted in the isolation and characterization of a new isoflavan, (3S, 4S)-2′,4′-dihydroxy-3′-methoxy-6,7-methylenedioxyisoflavan- 4-ol (1), and a new monoterpene, (4R,6S)-4-hydroxy-2,2,6-trimethyl-9-oxabicyclo [4.2.1] non-1(8)-en-7-one (2), together with four known flavonoids: geinstein (3), chrysin (4), chrysin -7-O-β-D-glucopyranoside (5) and 2″-O-α-L-rhamnosylorientin (6). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D, 2D NMR ((1)H, (13)C, COSY, TOCSY, HMBC and HSQC) and HRESIMS. The absolute configurations of 1 and 2 were established by the co…
Polyphenols and Pharmacological Screening of a Monarda fistulosa L. dry Extract Based on a Hydrodistilled Residue By-Product
This study aimed to determine the composition and content of polyphenols in the dry extract obtained from the hydrodistilled residue by-product of the wild bergamot (Monarda fistulosa L., Lamiaceae Martinov family) herb (MFDE) and to evaluate its safety and pharmacological properties. The total phenolic content (TPC) in the MFDE was 120.64 mg GAE/g. The high-performance liquid chromatography (HPLC) analysis showed the presence of a plethora of phenolic compounds, including hydroxycinnamic acids and flavone derivatives in the MFDE, with rosmarinic acid and luteolin-7-O-glucoside being the main components. With an IC50 value of 0.285 mg/mL, it was found to be a strong DPPH radical scavenger. …
Do differences in chemical composition of stem and cap of Amanita muscaria fruiting bodies correlate with topsoil type?
Fly agaric (Amanita muscaria) was investigated using a 1H NMR-based metabolomics approach. The caps and stems were studied separately, revealing different metabolic compositions. Additionally, multivariate data analyses of the fungal basidiomata and the type of soil were performed. Compared to the stems, A. muscaria caps exhibited higher concentrations of isoleucine, leucine, valine, alanine, aspartate, asparagine, threonine, lipids (mainly free fatty acids), choline, glycerophosphocholine (GPC), acetate, adenosine, uridine, 4-aminobutyrate, 6-hydroxynicotinate, quinolinate, UDP-carbohydrate and glycerol. Conversely, they exhibited lower concentrations of formate, fumarate, trehalose, α- an…
Antifungal activity of the carrot seed oil and its major sesquiterpene compounds.
Carrot seed oil is the source of the carotane sesquiterpenes carotol, daucol and β-caryophyllene. These sesquiterpenic allelochemicals were evaluated against Alternaria alternata isolated from the surface of carrot seeds cultivar Perfekcja, a variety widely distributed in horticultural practise in Poland. Alternaria alternata is one of the most popular phytotoxic fungi infesting the carrot plant. The strongest antifungal activity was observed for the main constituent of carrot seed oil, carotol, which inhibited the radial growth of fungi by 65% at the following concentration.
Polish Yellow Sweet Clover (Melilotus officinalis L.) Honey, Chromatographic Fingerprints, and Chemical Markers
A case study of Polish Melilotus officinalis honey was presented for the first time. Gas chromatography–mass spectrometry (GC-MS) (after steam distillation, Soxhlet extraction, ultrasonic solvent extraction, and solid phase extraction (SPE)) and targeted high performance liquid chromatography with a photodiode array detector (HPLC-PAD) were applied to determine the characteristic components of honey. While ubiquitous in most honeys, carbohydrates, terpene derivatives, and phenylacetic acid dominated in the Soxhlet extracts (25.54%) and in the application of SPE (13.04%). In addition, lumichrome (1.85%) was found, and may be considered as a marker of this honey. Due to the presence of these …
Chromatographic fingerprint of the volatile fraction of rare Hedera helix honey and biomarkers identification
Hedera helix (Irish ivy) honey is a very rare food product used in Ireland. The composition of the volatile fraction of this unique honey was studied for the first time using three different extraction procedures (SPE, USE and HS–SPME) and analyzed with gas chromatography and mass spectrometry. As expected, the use of combined techniques resulted in the identification of the detailed composition of honey volatiles. Identified constitutes belongs to the different chemical classes. The presence of 4(1H)-quinolinone, myrtenal and phenylacetonitrile was proposed as biomarkers of the botanical origin of ivy honey. Moreover, they are not widely widespread among honeys of different botanical origi…
Phytochemical Evaluation of Tinctures and Essential Oil Obtained from Satureja montana Herb
Winter Savory (Satureja montana L.) has been used in traditional medicine and as a spice or natural food preservative in the Mediterranean region for centuries. In this paper, some technological and analytical aspects of the S. montana tinctures development and an evaluation of the essential oil composition are provided. The total phenolic and flavonoid contents and phenolic compounds profile analyzed spectrophotometrically and by high-performance thin-layer chromatography (HPTLC), respectively, were evaluated in the developed tinctures. The results showed that the tinctures prepared from the S. montana herb by maceration or remaceration are rich in polyphenols, and there is an influence of…
Crotonic acid as a bioactive factor in carrot seeds (Daucus carota L.)
Water extracts from the carrot seed (Daucus carota L.) var. Perfekcja exhibit plant growth inhibitory properties against cress, cucumber, onion and carrot in a dose-dependant manner. This property results from the action of low-and high-molecular components of the extract. The low-molecular component was identified as crotonic acid ((E)-2-butenoic acid). Its presence was also confirmed in other late varieties of carrot. The determined strong herbicidal properties of crotonic acid and its availability after release to soil combined with its high level in seeds suggest that it might be considered as an allelopathic and autotoxic factor in the seeds.
Botanical Origin Authentication of Polish Phacelia Honey Using the Combination of Volatile Fraction Profiling by HS-SPME and Lipophilic Fraction Profiling by HPTLC
Eleven samples of Polish Phacelia tanacetifolia Benth., three Brassica napus and one Salix spp. honeys were characterized by melissopalynology and analysis of the compositions of their volatile fractions. Headspace solid-phase microextraction coupled with gas chromatography mass spectrometry (HS-SPME/GC–MS) using PDMS/CAR/DVB fiber was used for the isolation of low-molecular weight compounds which create a volatile fraction. To differentiate and indicate the most representative unifloral samples, chemometric techniques such as principal component analysis (PCA) and hierarchical-tree clustering (HTC) were applied to the dataset of the chromatographic fingerprints. Based on the obtained resul…
Research on Acute Toxicity and the Behavioral Effects of Methanolic Extract from Psilocybin Mushrooms and Psilocin in Mice
The pharmacological activities and acute toxicity of the psilocin (PC) and dried residues of the crude extracts of psychotropic mushrooms were investigated in mice. The hallucinogenic substances were effectively isolated, by using methanol, from the species of Psilocybe semilanceata and Pholiotina cyanopus, that were collected in the north-east region of Poland. The chemical analysis of these extracts, which was performed by liquid chromatography with mass spectrometry detection (LC-MS), indicated the presence of psilocin and other hallucinogenic substances, including indolealkylamines and their phosphorylated analogues. When the pure psilocin or fungal extracts were used, slight difference…
Recent advances in the research on herbicidally active aminomethylelebisphosphonic acids.
Influence of the mode of application of herbicidally active N-pyridylaminomethylenebi-sphosphonic acids on their uptake by plants was studied in some detail. The experimental evidence is given that accounts for a multiple mode of action of these herbicides.
Effect of extraction solvent on total phenolic content, total flavonoid content and antioxidant activity of Cetraria islandica
Oxidative stress may lead to a number of diseases such as atherosclerosis, nephrotoxicity, liver cirrhosis, cancers, diabetes, and Alzheimer disease. Medicinal plants are an important source of antioxidants. Therefore, the antioxidant potential of Cetraria islandica was evaluated in this work. The coarse powder of leaf of Cetraria islandica was extracted in Soxhlet apparatus, with ethanol (90%) and ethanolic extract of Cetraria islandica (EECI) was further processed for phytochemical screening, total phenol content, total flavonoid content, and various in vitro antioxidant assays. The phytochemicals present in EECI were glycosides, carbohydrates, triterpenoids, proteins and amino acids, gum…
Bioactive Alkaloids of Hallucinogenic Mushrooms
Abstract The aim of our chapter is to review recent developments in a group of medicinally important natural products–alkaloids, with reference to the structure–activity studies in respect of certain diseases. Alkaloids covered by our review come from mushrooms called “hallucinogenic.” Hallucinogenic compounds have been chemically identified in mushrooms belonging to various genera, e.g., Agrocybe, Amanita, Conocybe, Galerina, Gymnopilus, Hypholoma, Inocybe, Panaeolus, Psilocybe, Pholiotina, Pluteus, and Weraroa [J.W. Allen, Ethnomycol. J. Sacred Mushroom Stud. 9 (2012) 130–175]. One of the largest classes of alkaloids is indole alkaloids. Indoles are probably the most widely distributed he…
Phenolic compounds and abscisic acid as potential markers for the floral origin of two Polish unifloral honeys
The phenolic profiles of Polish honey samples from heather (Calluna vulgaris L.) and buckwheat (Fagopyrum esculentum L.) were determined. The phenolic components were isolated from honey samples using Amberlite-XAD-2 as a solid-phase extraction sorbent. For the determination of the composition of the honey extracts HPLC with photodiode array detector was applied. Identification and quantification of phenolics was performed by comparison of their retention times and UV spectra with those of standard solutions of pure reference substances and by using those references as external standards. From among 20 commercially available standards over 15 of them were identified as present in all analys…