E. A. Krasnov

Phenolic compounds from Filipendula ulmaria

A chromatographically inseparable crystalline mixture of the previously undescribed quercetin-4′-O-β-galactopyranoside and the known quercetin-3-O-β-glucopyranoside (isoquercitrin) in a 7:5 ratio was isolated from the extract of the aerial part of Filipendula ulmaria (L.) Maxim.

Medicinal plants: Filimarin, a new flavanol glycoside from filipendula ulmaria and its antioxidant activity

A new quercetin glycoside named filimarin was isolated from honeysweet (Filipendula ulmaria L. Maxim.) by colun chromatography over polyamide and silica gel. Based on chemical and spectral data, the structure of filimarin is identified as quercetin-4′-O-β-D-galactopyranoside. Results of voltammetric measurements showed that filimarin possesses pronounced antioxidant activity that is comparable with that of dihydroquercetin and ascorbic acid.

Isolation of grosshemin from the Siberian population of Centaurea scabiosa

Centaurea scabiosa (Asteraceae) has a wide range in the northern hemisphere and is common in Siberia, Europe, and Scandinavia [1]. This plant has long been interesting for its polyacetylene derivatives [2-4], after which Czech researchers discovered in it the germacranolide scabiolide [5, 6], which is structurally similar to cnicin [7]. We investigated the chemical composition of the air-dried aerial part of C. scabiosa from Tomsk District using extraction by diethylether and did not isolate scabiolide as reported earlier [6]. Isolation of Lactone 1. Raw material (0.5 kg) was soaked in CHCl3 (3 × 2 L) at room temperature. Filtration and removal of solvent produced a syrupy extract in 2% yield. The resulting product (10 g) was chromatographed over SiO2 with elution by CHCl3 and then CHCl3:(CH3)2CO mixtures with an increasing gradient of the latter. Removal of solvent from the CHCl3:(CH3)2CO (9:1) eluent produced a precipitate that had mp 200-201°C and Rf 0.13 (CHCl3) after washing with Et2O. Lactone 1 was a white with a cream tint finely crystalline powder, mp 200-201°C, lit. mp [10] 205°C. The IR spectrum had the following absorption bands (ν, cm-1): 3475 (OH), 1740 (C=O of a 5-membered ring conjugated to an unsaturated bond), 1650 (C=O), 1450 and 1410 (=CH2). Chromatography of the CHCl3 extract isolated grosshemin (1), which has been known since 1964 [8]. Its correct structure was established by Breton et al. [9]; the stereochemistry, by Samek et al. [10]. The latest publication did not completely assign the signals for H-1 and H-4 in the PMR spectrum and did not describe the signals for H-2 and H-5 (in DMSO-d6 solution).

Isolation of repin from the aerial part of Centaurea scabiosa

Centaurea scabiosa L. (Asteraceae) is of great scientific and practical interest among the flora of Siberia. Its chemical composition includes various groups of compounds, of which sesquiterpene lactones (SL) have special significance. The guaiane-type SLs grosshemin and cynaropicrin were previously isolated for the first time from C. scabiosa and identified [1, 2]. Herein we report the isolation from the aerial part of C. scabiosa of another guaianolide, repin. The total SLs were separated over a column of silica gel (sorbent:compound ratio 30:1) with elution by petroleum ether and a gradient of petroleum ether:EtOAc with increasing fraction of the latter. Elution of the column by petroleum ether:EtOAc (90:10) afforded a brownish-yellow oil that was a mixture of eight compounds according to TLC. It was rechromatographed over a column of silica gel (sorbent:compound ratio 50:1) with elution by hexane and hexane:EtOAc. Removal of solvent from fractions eluted from the column by hexane afforded a colorless oil with crystalline inclusions that was soluble in benzene and CHCl3; partly soluble in EtOH, EtOAc, Et2O, and hexane; and practically insoluble in H2O. Purification of the fraction with hexane followed by work up of the residue with EtOH (80%) isolated colorless crystals, mp 153–155°C (EtOH). IR spectrum (KBr, , cm–1): 3500 (OH), 1767 ( -lactone CO), and 1730 (ester). The PMR spectrum of the isolated compound (Table 1) showed doublets at 2.77 and 3.21 ppm with SSCC 6.0 Hz in addition to a singlet for methyl protons CH3 (19) that were characteristic of epoxymetacrylic acid in the C-8 position of the guaiane skeleton. Resonances of exocyclic methylene protons conjugated to a -lactone ring carbonyl were also found as a pair of doublets at 6.15 and 5.55 ppm. Resonances of protons of a second exocyclic methylene were observed as broad singlets at 5.12 and 4.96 ppm. A resonance at 4.90 ppm belonged to a hemiacyl proton. Table 1 presents the PMR and 13C NMR spectra. The compound was identified as the guaiane-type SL repin based on the physicochemical properties and spectral data [3]. It was isolated from the first time from C. scabiosa. Thus, column chromatography over silica gel isolated for the first time the guaianolide repin from the aerial part of C. scabiosa. Repin was characterized before as having pronounced antibacterial and antifungal activity against Entamoeba histolytica and Trichomonas vaginalis [4].

Flavonoid Content in the Aerial Part of Saussurea Controversa DC (Asteraceae)

A method for spectrophotometric determination of the flavonoid content in the aerial part of Saussurea controversa DC was developed. The amount of flavonoids calculated as rutin varied from (0.37 ± 0.07) to (0.73 ± 0.02)% depending on the collection year and storage time.

Experimental Simulation of Traumatic Osteomyelitis in Rats

A model of traumatic osteomyelitis in rats is created. The disease development was evaluated by bone marrow myelograms, results of scintigraphy, and histological studies.