U. N. Zainutdinov

Structure-Activity Relationship for Hemostatic Lagochilin Diterpenoids

The structure-hemostatic activity relationship of lagochilin and its natural and synthetic derivatives was investigated.

Mass spectrometry of metastable ions from lagochiline-type diterpenoids

Low-and high-resolution mass spectra and spectra of metastable ions were studied using direct analysis of daughter ions (DADI) and metastable defocusing (MD) of lagochiline-type diterpenoids. Patterns in their fragmentation were found.

QUANTITATIVE DETERMINATION BY PMR SPECTROSCOPY OF LAGOCHILIN IN THE SUBSTANCE AND TABLETS OF THE MEDICINAL PREPARATION INEBRIN

A modified method of additions in PMR spectroscopy was described for quantitative determination of the main active principle in preparations. The effectiveness and reliability of the method was approved for quantitative analysis of the active principle lagochilin in the substance (2.0%) and tablets (0.85%) of the commercial medicinal preparation inebrin.

Preparation and Physicochemical and Biological Properties of Molecular Associates of Lagochilin and Lagochirsine with Glycyrrhizic Acid and its Monoammonium Salt

Molecular associates of lagochilin and lagochirsine with glycyrrhizic acid and its monoammonium salt in various molar ratios were prepared. Their IR spectra, several physicochemical properties, and hemostatic activities were discussed.

Lipids from Seeds of Lagochilus inebrians

The family Lamiaceae is one of the most numerous with about 300 plant species [1]. The flora of Uzbekistan includes 201 species (41 genera) of this plant family [2]. Plants of the family Lamiaceae are interesting because they contain significant amounts of biologically active compounds with broad spectra of activity. Plants of this family have practical significance because many of them are valuable oil bearers [3] and sources of essential oils that are used in the medical, pharmaceutical, cosmetics, and food industries [4]. Therefore, chemical studies of Lamiaceae essential oils are highly valuable. Fatty oils from seeds and other organs of Lamiaceae plants are poorly studied despite their use on an industrial scale [1]. Recently, research on detailed chemical studies of the lipids has increased. Specifics characteristic of a certain species can be found by accumulating and systematizing data on the fatty-acid (FA) composition of reserve lipids. These can be used as additional classification signatures. This is especially important because several controversial issues regarding the systematics of the Lamiaceae family are currently being discussed [5]. Therefore, we studied for the first time free and polar lipids from ripe seeds of Lagochilus inebrians Bunge that were collected in Bukhara Oblast of Uzbekistan in 2014. Free lipids (FL) were extracted from ground seeds by petroleum ether (bp 72–80°C); polar lipids (PL), from defatted material by CHCl3–MeOH (2:1, v/v). Their yields were 24.15 and 1.13 mass% (of seeds), respectively. Furthermore, PL were separated into FL, glyco(GL), and phospholipids (PhL) by column chromatography over silica gel in order to determine the PL content and to remove traces of FL in the PL. Their yields were 10.46, 53.04, and 36.50 mass% (of PL), which was 0.11, 0.61, and 0.41 mass% (of seeds). Parameters of seeds of L. inebrians are given below:

Redetermnation of lagochiline monohydrate

In the title compound, C20H36O5·H2O, previously studied by film methods [Vorontsova et al. (1975 ▶). Izvest. USSR Ser. Chem. 2, 338–343], the H atoms have been located and the absolute structure (seven stereogenic centres) established. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming a three-dimensional network.

Lagoden dimethylformamide hemisolvate dihydrate: absolute configuration, dipolar interactions and hydrogen-bonding interactions.

Lagoden (L.3H2O, where L is Na+.C20H33O6-; sodium 3beta,16,18-trihydroxy-8,13-epi-9,13-epoxylabdan-15-oate trihydrate) is widely used as an effective haemostatic agent. It has been crystallized from dimethylformamide (DMF) as sodium 3beta,16,18-trihydroxy-8,13-epi-9,13-epoxylabdan-15-oate dimethylformamide hemisolvate dihydrate, Na+.C20H33O6-.0.5C3H7NO.2H2O or L2.DMF.4H2O, and the asymmetric unit contains two of the latter formulation. The four symmetry-independent Na+ cations and lagoden anions, one DMF molecule and six of the eight symmetry-independent water molecules assemble into a one-dimensional polymeric structure via dipolar and hydrogen-bonding interactions. The lagoden anions coordinate to the Na+ cations via the carboxylate groups and the two primary hydroxy groups, whereas the secondary OH groups are solely involved in hydrogen bonding. Two of the four symmetry-independent lagoden anions act in a chelating mode, forming seven-membered chelate rings. The absolute structure, based on anomalous dispersion data collected at 130 K with Cu Kalpha radiation, confirms an inverted configuration at chiral centres C8 and C13 (labdane numbering) relative to the labdane skeleton.

X-ray structure of lagochirsine

The molecular structure of the lagochilin diterpenoid lagochirsine was determined by x-ray structure analysis. The crystallographic investigations were conducted on an automated four-circle STOE/STAD14 diffractometer at room temperature. The crystals were trigonal, space group P32 (No. 145), C20H32O5, a = b = 14.289(2) Å, c = 8.2320(16) Å, V = 1455.6(4) Å3 , Z = 3, Dcalc = 1.206 g/cm3, R = 0.065 (Rw = 0.1368).

Ionophoric and complexant properties of Lagochilin derivatives

The ionophoric and complexant properties of synthetic derivatives of lagochilin, 3,18-O-isopropylidenelagochilin and 3,18-O-ethylidenelagochilin, were studied by BLM methods, conductometry, and IR spectroscopy. The ionophoric activity was found to be highly selective for divalent cations. Studies of the electrical conductivity of alkaline-earth metal salts in the presence of the lagochilin derivatives and analysis of their IR spectra have shown that they can form complexes with various ratios of metal ions.

X-RAY STRUCTURE OF LAGOCHIRSIDINE AND DI-o-CYCLOHEXYLIDENELAGOCHILIN

The structures of two diterpenoids from the lagochiline group, lagochirsidine and di-o-cyclohexylidenelagochilin, were determined by x-ray structure analysis.