A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis

A set of two diastereomers of phenylcyano glycosides, (7S)- and (7R)-phenylcyanomethyl 1'-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1, 2), were isolated from the methanol extract of dried vines of P. quadrangularis. The absolute configurations of the benzylic methine centers were determined mainly by the comparison of 13C NMR spectra of these compounds, prunasin (3) and sambunigrin (4), of which the last two cyanoglycosides are known to have (R)- and (S)-configurations, respectively.     

UTLC of Flavonols in Sambucus nigra Flowers

JPC – Journal of Planar Chromatography – Modern TLC -     

A new acid from the oil of the seeds of Sambucus nigra

Summary A new keto hydroxy acid (I) C₁₈H₃₀O₆ has been isolated from the fatty oil of the seeds ofSambucus nigra in an amount of 2% of the total fatty acids. A study of its chemical properties and spectral characteristics has shown that it is probably 11-hydroxy-9,15,16-trioxooctadeconoic acid, and that it consists of a keto-enol mixture containing about 30% of the two equiprobable tautomers (II and III); it has been given the name of caprifolonic acid.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–8, January–February, 1972.     

Two new iridoid glycosides from the root barks of Sambucus williamsii Hance

Two new iridoid glycosides, named williamsoside C (1) and williamsoside D (2) were isolated from the root barks of Sambucus williamsii Hance. Their structures were established on the basis of extensive spectroscopic analysis (1D, 2D NMR and HRESIMS) and chemical studies as α-D-glucopyranosyl (1→2)-β-D-fructofuranosyl (4→6)-β-morroniside (1) and 7β-O-ethyl morroniside-(6'-O-7')-β-morroniside (2), respectively.     

Two new iridoid glycosides from the root barks of Sambucus williamsii Hance

Chemical investigation of the ethanol extract of the root barks of Sambucus williamsii Hance collected in the Heilongjiang province of China resulted in the isolation of two new iridoid glycosides, williamsoside A (1) and williamsoside B (2). Their structures were elucidated on the basis of extensive spectroscopic analysis (1D, 2D-NMR and HRESIMS) and chemical studies. Iridoid glycosides have for a long time been considered as characteristic ingredients of S. williamsii. However, the presence of iridoid glycosides with apiofuranosyl moieties in S. williamsii is reported for the first time in this study.     

Electrochemical detection of cyanogenic glycosides after enzymatic post-column cleavage

Crude and partly purified extracts from Helix pomatia and linamarase from cassava were immobilized on columns packed with porous glass or silica and used as post-column reactors in the high-performance liquid chromatography of cyanogenic glycosides. Sodium hydroxide (2 M) was added to the flowstream after the enzyme-reactor resulting in the formation of cyanide, which was then detected at a silver electrode by an amperometric measurement at 0 V with reference to a silver-silver chloride electrode. The selective detection of cyanide allows measurements in a complex matrix. The response is linear and the detection limit is in the low picomole range.     

GC/MS analysis of thermally degraded neuromelanin from the human substantia nigra

Neuromelanin (NM) is a complex polymer pigment found in catecholaminergic neurons of the human brain. The structure, formation pathway, and physiological function of NM have not yet been clarified, but interest in this polymer has been sparked by the suggestion that NM is involved in cell death in Parkinson's disease. In the current study, pyrolysis-gas chromatography/mass spectrometry analysis was applied for structural investigation of NM isolated from the human substantia nigra, using synthetic eumelanin and pheomelanin-type pigments as reference materials. None of the heterocyclic, sulfur-containing compounds being characteristic thermal degradation products of cysteinyldopamine-derived units of synthetic pheomelanin standard was detected in the pyrolysates of natural NM. The results suggest that nigral pigment isolated from normal brain tissue does not contain benzothiazine-type monomer units. Pyrolytic experiments in the presence of a derivatizing agent allowed identification of high levels of saturated and monounsaturated straight-chain C14-C18 fatty acids and led to the conclusion that a part of a lipid component is chemically bound to the NM macromolecule. The nigral pigment was also shown to be tightly associated with an isoprenoid-type compound.     

Nonsaponifiable lipid components of the pollen of elder (Sambucus nigra L.).

Pollen of the elder (Sambucus nigra L.) was extracted with chloroform-methanol. The extract was separated by column chromatography into the following groups of compounds: hydrocarbons (8.7%). polycyclic aromatic hydrocarbons (0.2%), complex esters (5.2%), triglycerides (18.7%), hydroxy esters (27.9%), free fatty acids and alcohols (16.8%), free sterols (6.8%), and triterpenic alcohols (4.0%). The nonsaponifiable components (hydrocarbons, fatty acids, alcohols, and sterols) were examined in detail using spectroscopic and chromatographic methods (IR spectroscopy, GC, and GC-MS). The identified compounds were characterized by their mass spectra and Kováts retention indices. The double bond positions and their configurations in unsaturated compounds are also reported.     

Characterisation of Some Phytochemicals Extracted from Black Elder (Sambucus nigra L.) Flowers Subjected to Ozone Treatment

Elderflowers are a well-known source of bioactive compounds. The amount of isolated bioactive compounds may be increased by applying various abiotic and biotic factors. Gaseous ozone (10 and 100 ppm) was used in the process of preparing flowers. Next, the flowers were treated with sugar syrup to extract bioactive compounds. It was shown that this treatment, including the influence of extraction temperature, significantly affects the contents of polyphenols (liquid chromatography–mass spectrometry (LC–MS) methods) and vitamin C, as well as the antioxidant potential (cupric reducing antioxidant capacity (CUPRAC method)), the profile of volatile substances (head space–solid-phase microextraction (HS–SPME methods)) and the colour of the syrup (Commission Internationale de l’Eclairage (CIE) L*a*b* methods). The findings show that an increased dose of ozone and higher extraction temperature applied in the process of syrup production resulted in higher contents and different compositions of bioactive compounds. The highest contents of bioactive compounds were identified in syrup obtained from raw material treated with ozone for 15 min (concentration = 10 ppm) and extraction with sugar syrup at a temperature of 60 °C.     

Water-in-Oil-in-Water Double Emulsions as Protective Carriers for Sambucus nigra L. Coloring Systems

The use of natural colorants is needed to overcome consumer concerns regarding synthetic food colorants′ safety. However, natural pigments have, in general, poor stability against environmental stresses such as temperature, ionic strength, moisture, light, and pH, among others. In this work, water-in-oil-in-water (W₁/O/W₂) emulsions were used as protective carriers to improve color stability of a hydrophilic Sambucus nigra L. extract against pH changes. The chemical system comprised water and corn oil as the aqueous and oil phases, respectively, and polyglycerol polyricinoleate (PGPR), Tween 80, and gum Arabic as stabilizers. The primary emulsion was prepared using a W₁/O ratio of 40/60 (v/v). For the secondary emulsion, W₁/O/W₂, different (W₁/O)/W₂ ratios were tested with the 50/50 (v/v) formulation presenting the best stability, being selected as the coloring system to test in food matrices of different pH: natural yogurt (pH 4.65), rice drink (pH 6.01), cow milk (pH 6.47), and soy drink (pH 7.92). Compared to the direct use of the extract, the double emulsion solution gave rise to higher color stability with pH change and storage time, as corroborated by visual and statistical analysis.     

Synthesis of triterpene glycosides

Summary The acyl -D-glucopyranoside, the acyl -D-xylopyranoside, the acyl D- and L--arabinopyranosides, and the acyl -D-lactoside of 18-glycyrrhetic acid, and also the acyl -D-lactoside of 18-glycyrrhetic acid have been synthesized. The acid and alkaline hydrolysis of the compounds obtained has been studied.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 1, pp. 13–19, 1968     

Synthesis of triterpene glycosides

Summary 1. The acyl--D-glucopyranosides, acyl--D-xylopyranosides, and acyl--L-arabinopyranosides of oleanolic and ursolic acids have been synthesized for the first time.2. A method for the synthesis of acyl glycosides of triterpene hydroxyacids with hindered carboxy groups has been developed.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 6, pp. 405–410, 1966     

Synthesis of diterpene glycosides

Summary Mono-, di-, and linear triglycosides of a diterpene alcohol, derived from abietic acid and glucose have been synthesized employing peracetylbromo--D-glucose (4) and maltose derivatives5 and8 as glycosyl donors. The triglycoside14 exhibits slight haemolytic activity.

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Synthese von Diterpenglycosiden

Zusammenfassung Es wird die Synthese von Mono-, Di-, und linearen Triglycosiden aus einem von Abietinsäure abgeleiteten Diterpenalkohol beschrieben. Als Glycosyldonoren wurden neben Peracetobrom--D-glucose (4) die Maltosederivate5 und8 verwendet. Das Triglycosid14 zeigt schwache hämolytische Aktivität.