The analysis of Celandine extracts (Chelidonium majus L.) by 1H NMR method makes it possible to identify the main alkaloids – derivatives of phenanthridine, protoberberin and protopin, and the use of the qNMR method provides information with satisfactory accuracy about the content of these alkaloids. The content of alkaloids determined in the composition of Celandine extracts by the qNMR method (0.35%) is 2 times lower than when using the spectrophotometric determination procedure described in the GF of the Russian Federation XIV (0.72%). The extraction results according to the methods given in the State Pharmacopoeia of the Russian Federation of the XIV edition and in the State Pharmacopoeia of the USSR of the IX edition give similar results: the same alkaloids are found in the extracts – chelidonin, stylopine and protopine, and the total content of alkaloids is 1.6-1.8 times less than when extracting the same raw material samples by the method insistence. When extracted by infusion, the main alkaloids in the extracts are dihydrosanguinarin, chelidonin, stylopine, berberine and coptisin.
Background: In recent years, microwave radiation has been widely used in organic synthesis, including solvent-free mode. However, the reaction conditions of phthalic anhydride with amino acids under solvent-free microwave activation have not been studied so far. Objective: In the present work, the effect of microwave activation on the interaction of phthalic anhydride with amino acids in solvent-free conditions has been studied in detail. Methods: The microwave heating dynamics of phthalic anhydride, glycine and their equimolar mixture under microwave conditions have been investigated, and the dependence of the heating rate on the microwave power is defined. Results: The common conditions for the synthesis of phthaloylamino acids have been determined as continuous heating at a power of 200 W at 130 °C for 5-6 min and additional heating for 5-10 min at a temperature close to the melting point of the corresponding amino acid. We apply the developed two-step solvent-free microwave reaction protocol successfully for the synthesis of phthaloyl derivatives of glycine, alanine, β-alanine, 4-aminobenzoic acid, γ-aminobutyric acid, isoleucine, leucine, phenylalanine. Conclusion: Reaction conditions for synthesizing phthaloylamino acids by microwave activation without solvent have been established. The solvent-free microwave reaction between phthalic anhydride and amino acid has been found to proceed in the melted phthalic anhydride.
The complex of plant metabolites as a set of certain substances can be characterized by chemical and physicochemical methods of analysis. A chemical characteristic involves the identification of a set of individual substances - chemical markers unique to a selected plant object; and the entire visible set of components as a characteristic profile – a "chemical fingerprint".The object of the study is the poppy of Kuvaev (Papaver kuvajevii). A new kind of poppy; described in 2003. Endemic. Perennial. It grows in the steppe belt on the slopes of the mountains; rocks; screes; pasture steppes. Blossoms in May – August. Seed multiplication June – September.In this paper; a scheme of extraction procedures for the spectroscopic profiling of the Kuvaev poppy has been developed. The crushed air-dry aerial part of the plant (without capsules) was extracted in the Soxhlet apparatus sequentially with solvents (in order of increasing their polarity). IR; NMR 1H and 13C profiles were recorded for each extract. The content of taxifillin in the sample is determined by quantitative NMR analysis (q-NMR).
A new Papaver species, P. kuvajevii Schaulo et Sonnikova, which is a rare species of the flora of western Sayan (relict, endemic), was discovered in 2003 at the Sayano-Shushenskii Natural Biosphere Reserve and described [1]. An investigation of the chemical composition of P. kuvajevii would prompt its industrial production while preserving the genetic resource of this natural endemic species if valuable biologically active constituents were found.The goal of the present work was to study the alkaloid composition of P. kuvajevii. Herein we communicate results from a GC-MS investigation of the alkaloid composition of this plant.Plant material (aerial part, stems, leaves, flowers, pods) was collected in July 2012 at Sayano-Shushenskii Natural Biosphere Reserve. Herbarium specimens are preserved at the Reserve Herbarium. The yield of substances from air-dried and ground aerial parts (285 g) that were extracted by EtOH in a Soxhlet apparatus was 12.6% (36.0 g). The EtOH extract was worked up with dilute H 2 SO 4 and separated by fractional extraction into fractions according to basicity using the classical method [2].Extraction by CHCl 3 produced alkaloid fraction AC (36.9 mg, 0.01% relative to starting air-dried raw material) after basicification by Na 2 CO 3 (pH 8) and alkaloid fraction B (83.8 mg, 0.03%) after basicification by NaOH (pH 11). The fractions were analyzed by GC-MS on an HP 5890 Series II GC with an HP 5971 mass-selective detector (EI, 70 eV) and HP-5 capillary column (5% diphenyl-95% dimethylsiloxane, 30 m u 0.25 mm, 0.25 Pm) using He carrier gas at 1 mL/min. The column temperature regime was 50°C (2 min), 50-300°C (10 °C/min), and 300°C (30 min). The vaporizer temperature was 280°C; ion-source, 170°C. The scan rate was 1.2 scan/s in mass range 29-650 amu. Constituents were identified by comparing total mass spectra with those in the NIST08 and W8N08 databases.The principal alkaloids in both fractions were amurensinine (1) and mecambridine (syn. oreophylline) (2). In addition to these, minor alkaloids amurensine (3) and D-allocryptopine (4) were also identified (Table 1).Fraction AC was separated by preparative TLC on SiO 2 F 254 plates (Merck) using CHCl 3 -EtOH (15:1, v/v) to afford six fractions that were analyzed by GC-MS. Fractions AC-4 and AC-5 were enriched in amurensinine (1). Fraction B was also separated by preparative TLC under the same conditions and afforded seven fractions that were analyzed by GC-MS. Fraction B-3 was enriched in mecambridine (2); fraction B-5, 1. Fractions AC-4, AC-5, and B-5 were combined. PMR spectra of additionally purified 1 (2.3 mg, 0.00080%) and 2 (3.1 mg, 0.00108%) were recorded. The structures of isolated alkaloids 1 and 2 were confirmed by PMR spectral data and comparison with those reported [3,4].
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