Herein, comprehensive data of NMR, MS, IR, and gas chromatography (RI) obtained by GC-MS on commonly used capillary columns of different polarity (non-polar DB-5MS and polar HP-Innowax) of a series ...of esters of all constitutional isomers of hexanoic acid with a homologous series of ω-phenylalkan-1-ols (phenylmethanol, 2-phenylethanol, 3-phenylpropan-1-ol, 4-phenylbutan-1-ol, and 5-phenylpentan-1-ol) and phenol, in total 48 chemical entities, were collected. The created synthetic library allowed the identification of a new constituent of the
essential oil (3-phenylpropyl 2-methylpentanoate). The accumulated spectral and chromatographical data, as well as the established correlation between RI values and structures of regioisomeric hexanoates, provide (phyto)chemists with a tool that will make future identification of related natural compounds a straightforward task.
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•A series of esters of diastereomeric menthols was analyzed by GC–MS.•A foolproof identification procedure for these aroma important esters was suggested.•EI Mass Spectral Libraries ...recorded on SQ and QIT mass detectors were created.•GC RI data on non-polar HP-5MS and polar HP-Innowax columns are included therein.•A collection of MS and GC data was compiled and is available as supplementary data.
A comprehensive data collection of mass spectral and gas chromatographic data of a series of esters of diastereomeric menthols (menthol, isomenthol, neomenthol, and neoisomenthol), in total 150 chemical entities, obtained by GC–MS on commonly used capillary columns of different polarity (non-polar HP-5MS and polar HP-Innowax), was created. Also, MS libraries containing electron ionization MS recorded on single quadrupole as well as on quadrupole ion-trap mass detectors together with the RIs on non-polar and polar columns were compiled (available as supplementary materials). The results point out to frequent misidentification of neoisomenthyl acetate as isomenthyl acetate in the literature, and the means of how to resolve this issue was suggested. The outcomes of this study provide chemists and food technologists with a useful tool in the field of food analysis of compounds with important food aroma properties.
•A new natural product 5-phenylpentyl isothiocyanate (PhPeITC) was found in horseradish.•The first direct proof of the existence of a 5-phenylpentyl glucosinolate in nature.•PhPeITC and four related ...isothiocyanates were synthesised and extensively tested.•PhPeITC possesses spasmolytic activity 100 times more potent than papaverine.•Horseradish constituents showed significant cytotoxicity and antimicrobial activity.
Detailed analyses of horseradish autolysates led to the identification of a new natural product, 5-phenylpentyl isothiocyanate (PhPeITC). The structural assignment was corroborated by synthesis, and the identity unequivocally established by spectral means. The occurrence of PhPeITC is the first direct proof of the existence of a 5-phenylpentyl glucosinolate in the aerial parts of this species as one of the possible “mustard oil” precursors. To verify its possible contribution to the horseradish functional food status, horseradish above- and underground autolysates, together with five ω-phenylalkyl isothiocyanates were tested for their spasmolytic, cytotoxic and antimicrobial activities. Specifically, the cytotoxic effect on Caco-2, HeLa (cancer) and MDCK (non-cancer) cell lines was established. Additionally, the five tested ITCs exerted significant spasmolytic activity (on rat distal colon), with PhPeITC being almost 100 times more potent than papaverine. A non-selective antimicrobial activity of all ITCs was revealed in the case of 6 bacterial and 2 fungal strains.
A detailed chemical analysis of the essential oil of Asphodelus albus roots performed in this work, in combination with a chemical synthesis approach - the synthesis of selected compounds and their ...detailed spectral analysis - has led to the identification of a series of new natural products, the esters of furan-3-ylmethanol: furan-3-ylmethyl 2-methylpropanoate, furan-3-ylmethyl butanoate, furan-3-ylmethyl 2-methylbutanoate, furan-3-ylmethyl 3-methylbutanoate, furan-3-ylmethyl pentanoate, furan-3-ylmethyl 4-methylpentanoate, and furan-3-ylmethyl hexanoate.
•Previous chemical and toxicological data on the ethnomedicinally valued species Achillea falcata L. (Asteraceae) are scarce.•As confirmed by GC-MS and extensive NMR, trans-sabinol and its esters are ...the dominant A. falcata volatiles.•trans-Sabinyl formate and tiglate represent newly discovered natural products.•These compounds have moderate acute toxicity and acetylcholinesterase inhibitory activity.•Three complementary antinociceptive assays showed that the esters influence both the peripheral and central nervous systems.
Herein we report on the comprehensive chemical analysis of the essential oils obtained from above- and underground parts of a previously unreported chemotype of Achillea falcata L. (Asteraceae) and, for the first time, on the biological/toxicological profile of its dominant/newly discovered volatile metabolites. Detailed spectral analyses, in combination with chemical synthesis and theoretical study, of selected constituents, enabled the identification of trans-sabinol and its esters – the formate, tiglate (new compounds), acetate, butanoate, isobutanoate, 2-methylbutanoate and 3-methylbutanoate – in both aerial and underground parts of A. falcata. Evaluation of acute toxicity in Artemia salina model, in vitro and in silico (molecular docking) evaluation of acetylcholinesterase inhibitory activity and in vivo (mice) evaluation of antinociceptive activity (hot plate, tail immersion and acetylcholine-induced abdominal writhing tests) of trans-sabinol and its esters suggested that they may interact with different targets in crustacean/mammalian organisms. Alongside moderate acute toxicity (LD50 (48 h) = 0.03–0.26 mmol/L), the tested compounds exert influence on both the peripheral and central nervous systems (in the hot plate test, trans-sabinyl tiglate, at 50 mg/kg, produced a 140% baseline increase 15 min after the treatment) and to moderately inhibit acetylcholinesterase (at the concentration of 20 µg/mL, these compounds caused a reduction of acetylcholinesterase activity up to 40%).
The present work was undertaken to determine the total phenol, flavonoid and tannin content in five extracts of Origanum vulgare growing wild in southwest Serbia as well as to evaluate antioxidant ...and antimicrobial activity towards 29 strains of human pathogenic and food spoilage bacteria and fungi. In order to define a chemotype of this O. vulgare, chemical composition of essential oil was determined. The major compounds were: sabinene, terpinen-4-ol, 1.8 cineole, γ-terpinene and caryophyllene oxide. The concentrations of total phenols were examined using Folin–Ciocalteu reagent and the obtained values ranged from 84.5 to 235 mg GA/g. By using aluminium chloride method, the concentrations of flavonoids were obtained and the values ranged from 57.1 to 132 mg RU/g. In determining the amount of tannins, the method with butanol–HCl reagent was used and the obtained values were between 1.25 and 4.02 mg CCh/g. Antioxidant activity was evaluated by measuring the scavenging capacity of extracts on DPPH. Tested extracts expressed strong scavenger activity with IC50 values between 34.5 and 86 μg/ml. The ethanol extract was the most active. The strongest antibacterial activity, determined by microdilution method, was detected on G+ bacteria such as Bacillus species and Staphylococcus aureus, obtaining minimal inhibitory concentration (MIC) 0.16 mg/ml while antifungal activity was moderate with MICs between 2.5 and 20 mg/mL.
•We determined chemical composition of essential oils.•We examined five different extracts of aerial parts from oregano.•All extracts showed significant antimicrobial effect.•Good antioxidative activity.
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► Yarrow volatiles are more toxic to mice (LD50 853mg/kg) than thujone containing oils. ► Achillea umbellata constituents showed anxiolytic, analgesic and paralyzing activity. ► The ...oil is comprised of a rare monoterpene alcohol fragranol and its esters. ► A. umbellata oil exerts a different effect on prokaryotic and eukaryotic cells. ► Fragranol is believed to be the main carrier of the observed activity/toxicity.
Many plant species are used for medicinal purposes without the knowledge of their possible toxic effect. The ethnopharmacologically renowned genus Achillea L. (Asteraceae) is even more troublesome in this respect since different taxa are believed to have the same beneficial properties as A. millefolium. According to the median lethal i.p. dose (LD50=853mg/kg, mice), the volatiles of Achillea umbellata Sibth. et Sm. are more toxic than the thujone-containing essential oils (LD50>960mg/kg). A GC–MS analysis of A. umbellata oil revealed the presence of a series of fragranyl esters (six new natural products). The major constituents of this oil, the rare monoterpene alcohol fragranol and fragranyl acetate, and one more ester (benzoate), as well as the oil itself, showed antianxiety, analgesic and, in some instances, paralyzing properties at 50–150mg/kg but these are very likely sign of intoxication and not of possible beneficial effects of the plant volatiles. Testing of antimicrobial activity demonstrated that the oil possesses moderate activity against pathogenic microorganisms, but the effect of the oil differs in pro- and eukaryotic cells. According to the results obtained, fragranol may be considered as the main active principle responsible for the observed activity/toxicity.
The essential oils obtained by hydrodistillation of Geranium purpureum and G. phaeum were characterized by GC‐FID and GC/MS analyses (the former for the first time in general). In total, 154 ...constituents were identified, accounting for 89.0–95.8% of the detected GC peak areas. The investigated essential oils consisted mainly of fatty acids and fatty‐acid‐derived compounds (45.4–81.3%), with hexadecanoic acid and (E)‐phytol as the major components. The chemotaxonomic significance of the variations in the essential‐oil composition/production of the presently and previously investigated Geranium and highly related Erodium taxa from Serbia and Macedonia was assessed by multivariate statistical analyses. The main conclusions drawn from the high chemical similarity of the two genera, visible from the obtained dendrograms and biplots, confirm the close phylogenetic relationship between the investigated Geranium and Erodium taxa, i.e., that there is no great intergeneric oil‐composition variability. Changes in the composition and production of essential oils of the herein investigated taxa and 60 other randomly chosen species belonging to different plant genera were also statistically analyzed. The results put forward pro arguments for the oil‐yield–oil‐composition correlation hypothesis.
Achillea ageratifolia subsp. serbica is a poorly investigated endemic of the
Balkan area and there are almost no data about the potential application of
this plant. The purpose of this study was the ...investigation of the
phytochemical composition, antioxidant, antimicrobial, and antibiofilm
activity of its water, acetone, and ethyl acetate extracts. The phenolic
composition and flavonoids were established using high-performance liquid
chromatography with photodiode array detection (HPLC-PDA) analysis, while
the chemical composition of the ethyl acetate extracts of the aerial parts
of the plant was investigated by gas chromatography-mass spectrometry (GC
and GC-MS). Antioxidant and antimicrobial activity, as well as the
inhibition ability of biofilm formation on Staphylococcus aureus ATCC 25923
and Pseudomonas aeruginosa ATCC 27853 biofilms, were also investigated. The
total phenolic content ranged from 18.61 mgGAE/g to 43.78 mgGAE/g of
extract. The total flavonoid content ranged from 10.79 mgRUE/g to 34.02
mgRUE/g. The acetone and ethyl acetate extracts of the aerial parts
contained chlorogenic acid, myricetin, apigenin, and luteolin. Analysis of
the volatile specialized metabolites in the ethyl acetate extract of the
aerial parts allowed for the identification of thirty-two constituents. The
highest antioxidant activity was detected in the water extract of the aerial
parts of the plant (IC50 = 641.06 ?g/ml) and in the ethyl acetate extract of
the root (IC50 = 675.33 ?g/ml). Bacillus subtilis and S. aureus showed
higher sensitivity to the tested extracts, while the antifungal activity of
the marked extracts was significant. All extracts showed a moderate
inhibitory effect on the ability of biofilm formation of P. aeruginosa ATCC
27853, while only the ethyl acetate inflorescence extract showed an effect
on the biofilm formation of P. aeruginosa ATCC 27853. The tested extracts
showed the potential for further investigation and possible application as
biofungicides.
Detailed GC and GC‐MS analyses of the essential oils and Et2O extracts of two Xeranthemum species – X. cylindraceum and X. annum – resulted in the identification of 254 components, in total. ...Terpenoids constituted the major part of both X. cylindraceum and X. annum essential oils and extracts (51.8–65.7%, and 50.7%, resp.). Among the sesquiterpenoids, the extracts of both investigated taxa contained the guaianolide xerantholide, its 11,13‐dihydro derivatives, and two additional sesquiterpene lactones: an eudesmanolide, 11,13‐dihydroisoalantolactone, and a pseudoguaianolide, confertin. The last two lactones and both isomers of 11,13‐dihydroxerantholide have not been previously detected in Xeranthemum species. The isolated extracts of X. cylindraceum and X. annum were tested in a broth microdilution assay against a panel of microorganisms. The tested extracts demonstrated significant antimicrobial inhibitory activity, ranging from 30 to 260 μg/ml, being most active against Bacillus cereus and Staphylococcus aureus, an important human pathogen, with MIC close in value to those of chloramphenicol. Chemotaxonomic significance of the sesquiterpene lactones' distribution in the taxa investigated in this study and those detected earlier in phylogenetically close species (up to the level of the tribe Cardueae) was also discussed.
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