The bushes ofPaliurus spina-christi Mill., also known as Christ's thorn or hold-tree, are widespread in all regions of Caucasus and Central Asia. This is a nectariferous flower-bearing fruit plant, the fruits having been used in folk medicine for the treatment of various disorders. Recently, it was reported that the ethanol extract of some parts of this plant exhibit antimicrobial activity [1].The leaves, flowers, and fruits of Paliurus spina-christi contain epigallocatechol, gallocatechol, catechol, rutin, isoquercetin, quercetin-3-rutinoside-7-rhamnoside, kaempferol-3-glycoside, fatty acids, and alkaloids [2 -5]. However, the fruits of this plant are still insufficiently studied with respect to pharmacological properties.The purpose of this work was to study the lipophilic and hydrophilic components of the fruits and seeds of Paliurus spina-christi, characterize the biological activity of these substances, and create a medicinal preparation on this base.We have succeeded in isolating a neutral lipid (NL) fraction (20%) from the plant seeds, which is a yellow oily fluid with the following characteristics: d 2~ 0.9227; n~ ~ 1,4778; iodine number, 102.6% 12; acid number, 4.5 mg KOH; unsaponifiable fraction, 1.2%.Investigation of the NL composition by methods of column chromatography, followed by analytical and preparative thin-layer chromatography of the narrow-band fractions, revealed a series of compounds belonging to the following classes (wt.%): hydrocarbons, 1.5; esters of fatty acids and sterols, 2.3; triacylglycerides (TAG), 90.5; free fatty acids (FFA), 2.2; diacylglycerides (DAG), 0.5; flee sterols, 0.8; monoacylglycerides, 0.3; unidentified compounds, 1.9.Fatty acids (FA) were isolated by alkaline hydrolysis from the fraction of basic acyl-containing lipids and analyzed (in the form of methyl esters) by gas chromatography (GC) on polar and medium-polarity immobile phases. The 1 Kutateladze Institute of Pharmaceutical Chemistry, Academy of Sciences of Georgia, Tbilisi, Georgia. 2 Deceased. 591UV spectrum of a hexane solution of FA exhibited no absorption bands; the IR absorption spectrum of FA displayed no bands due to the vibrations of transolefin bonds [6].As seen from data on the FA composition (Table 1), unsaturated 18 : 1 and 18 : 2 acids dominate in all classes of NL, while saturated components are mostly contained in the fraction of free fatty acids (FFA). The difference in the content of 18 : 0, 18 : 2, and 18 : 3 acids, detected by GC with polar and medium-polarity immoi~ile phases, is indicative of the presence of isomers of the unsaturated acids [7]. The structure of fatty acids was studied by fractionating their methyl esters with respect to the degree of saturation. This was achieved by preparative TLC oh silica gel impregnated with 15% AgNO s, followed by destructive oxidation of the isolated fractions with a periodate -permaganate reagent [8]. During TLC, methyl esters of diene and triene fatty acids partly separated into two isomer fractions, which were jointly desorbed. The TLC analysis s...
547.915The chemical composition of neutral lipids from seeds of Cercis siliquastrum, Sapium sebiferum, and Koelreuteria paniculata were studied. Characteristic features of their individual classes were established.Cercis siliquastrum L. (Judas tree), Sapium sebiferum L. Roxb. (Chinese tallow), and Koelreuteria paniculata Laxm. (goldenrain tree) grow well in Georgia, are easily propagated, and bear abundant fruit [1][2][3].Polar lipids from seeds of these plants were found at the Kutateladze Institute of Pharmaceutical Chemistry, Academy of Sciences of Georgia, to be active against growth of xenograft tumors of cancer cells [4]. We have previously reported the chemical composition of phospholipids from seeds of C. siliquastrum and S. sebiferum [4][5][6].Herein we report results from a study of neutral lipids (NL) from seeds of C. siliquastrum (ID), S. sebiferum (SD), and K. paniculata (MD).Air-dried ground seeds of ID, SD, and MD that were collected when fully ripe were extracted exhaustively with nhexane at room temperature to produce the NL. The total NL were obtained as oily yellow liquids up to 10% for ID and up to 20% for SD and MD.The physicochemical properties of NL from ID, SD, and MD, respectively, were as follows. Acid number (mg/KOH) 2.80, 23.39, 2.00; d 4 20 0.918, 0.924, 0.909; n D 20 1.475, 1.479, 1.473; saponification number (mg/KOH) 119.22, 142.40, 183.20; iodine number (%I 2 ) 145.33, 90.78, 88.80; ester number (mg/KOH) 116.42, 119.01, 181.20; moisture and volatiles (%) 3.1, 2.0, 1.8.TLC analysis using various solvent systems detected bands in the studied NL corresponding to hydrocarbons (HC), sterol esters (SE), triacylglycerides (TAG), free fatty acids (FFA), free sterols (FS), diacylglycerides (DAG), and unidentified components [5]. The NL of MD did not contain SE although bands for fatty-acid methyl esters (FAME) were detected.Adsorption chromatography of the total NL followed by preparative TLC (PTLC) of the mixed fractions isolated the individual classes.Fatty acids (FA) were isolated from the main acyl-containing lipids by alkaline hydrolysis. Their composition was determined by GC of the methyl esters [7][8][9][10]. Table 1 shows that NL of the studied seeds had a FA composition consisting of only 5-6 components. The FA of total lipids and TAG of ID were dominated by linoleic acid (66-64%); FFA and SE, palmitic. Total FA and FFA of SD were dominated by linoleic and oleic; TAG and SE, palmitic. NL of MD had a high (80%) content of oleic acid.FA of NL from ID and SD were converted to the methyl esters and separated by preparative TLC (Ag + ) using system 3. Fractions of saturated, monoenoic, dienoic, and trienoic acids were obtained.According to GC, FAME of saturated (1), monoenoic (2), dienoic (3), and trienoic (4) NL fractions from ID and SD seeds had the following composition (mass %):
The plants Sterculia platanifolia L. f. (Chinese parasol tree) (Sterculiaceae) and Hamamelis virginiana L. (American witchhazel) (Hamamelidaceae) have been used since antiquity in traditional medicine. Tincture of S. platanifolia is an official medicinal preparation used as a stimulant and tonic for asthenia, exhaustion, and reduction of muscle tone [1]. Leaves of H. virginiana are an ingredient of homeopathic preparations. The tincture and cream of extracts of this plant are used for vascular diseases [2-4]. Biological aspects of the growth and development of S. platanifolia and H. virginiana in the humid subtropics of Georgia have been studied. Recommendations for cultivation have been written. The plants have been cultivated at Kobulet Experimental Station for Medicinal Plants of the Institute of Pharmaceutical Chemistry. Both these species produce a large number of seeds, which prompted our interest in the study of their lipid composition.Air-dried ground seeds were extracted exhaustively with n-hexane at room temperature. Solvent was distilled off to afford neutral lipids (NL) as a yellow oily liquid for S. platanifolia (SP) (17.0%) and H. virginiana (HV) (12.0%).The physical chemical properties of the NL from SP and HV, respectively, were as follows: acid number (mg KOH), 12.0 and 4.5; d 4 20 -0.916 and 0.913; n D 20 -1.472 and 1.476; saponification number (mg KOH), 184.5 and 148.9; iodine number (% I 2 ), 76.6 and 171.3. TLC of NL from SP and HV on Silufol and silica gel plates (with 10% CaSO 4 ) in various solvent systems detected zones corresponding to hydrocarbons (HC), triacylglycerides (TAG), free fatty acids (FFA), free sterols (FS), 1,3-diacylglycerides (DAG), and phospholipids (PL). Column chromatography of NL with subsequent preparative TLC (PTLC) isolated from mixed fractions all basic NL classes [5, 6]. The ratios of individual classes were typical for lipids of higher plants. Total lipids and acyl-containing acids in them were hydrolyzed by KOH. Fatty acids (FA) were methylated by diazomethane [7] and analyzed by GC as the methyl esters [8] (Table 1).It has been found that NL from both plants have a simple fatty-acid composition and contain only 3-4 components, among which linoleic acid dominated.Phospholipids (PL) from defattted seeds of SP and HV were extracted and purified as before [5,9]. The yields of total phospholipids from SP and HV seeds were 0.21 and 0.14%, respectively.Total PL were analyzed and separated by two-dimensional PTLC on silica gel. Quantitative analysis of pure PL was performed by spectrophotometric methods [10]. Table 2 shows that the main component of PL from SP is phosphatidylcholine (PC). The regular distribution PC > phosphatidylinosite (PI) > phosphatidylethanolamine (PE) was observed. The PL from HV had a high content of PI, which was unusual for plant lipids. The presence in both plants of N-acylated derivatives of PE and lyso-phosphatidylethanolamine (lPE) was noteworthy.
and E. P. KemertelidzeAbies nordmanniana (Stev.) Spach. or Caucasian fir (Pinaceae L/ND) is an evergreen conifer up to 50 m in height that is widely distributed in the Caucases and occupies approximately 6% of its forested area. In Turkey, it grows on slopes of the Pontic mountains [1, 2]. Fir oil obtained from the seeds is used in perfume and cosmetic formulations and in medical practice.Neutral lipids (NL) were extracted from air-dried ground seeds by n-hexane and hot pressing. The yield of total NL was 15-20% as a yellow oily liquid with the following limiting properties: acid number, <43 mg/KOH/g; d 4 20 0.960; n D 20 1.475-1.498; moisture and volatile substances, <16.5%; saponification number, 90-220 mg/KOH/g; iodine number, 115-190% I 2 .TLC was performed on Silufol plates and silica gel (L 100/160) using hexane:diethylether:acetic acid (87:14:1). Total NL gave bands corresponding [3] to hydrocarbons (HC), sterol esters (SE), methyl esters of fatty acids (MEFA), triacylglycerides (TAG), free fatty acids (FFA), free sterols (FS), 1,3-diacylglycerides and 1,2-diacylglycerides (DAG), monoacylglycerides (MAG), and phospholipids (PL). The ratios of separate NL classes were typical for oils from higher plants. The dominant class was TAG.All separate classes were isolated from the crude fractions during a study of the NL composition using column chromatography (CC) and preparative TLC (PTLC). Alkaline hydrolysis of the principal acyl-containing lipids isolated fatty acids (FA). Their composition was determined by GC of the methyl esters [3][4][5]. Table 1 shows that NL from seeds of A. nordmanniana contained eight FA, the principal mass of which was unsaturated FA, in particular, oleic acid (18:1) and linoleic acid (18:2), which dominated all classes. The exception was SE from lipids isolated by direct pressing of seeds, where 97.7% was palmitic acid (16:0); the remaining 2.3%, lauric acid. Mainly this distinguished NL obtained by n-hexane extraction and direct pressing of seeds from each other. The presence of isopalmitic acid in the FFA is also interesting.The polar fraction was extracted by the Folch method [6] in order to investigate PL from defatted A. nordmanniana seeds. The yield of total PL purified of ballast substances [3] was 0.045% of the raw material mass. PL were identified by twodimensional TLC on silica gel using CHCl 3 :CH 3 OH:NH 4 OH (25%) (65:30:5) and CHCl 3 :CH 3 OH:CH 3 CO 2 H (glacial):H 2 O (170:25:25:6).PL were identified by spraying with Vaskovsky and Dragendorff's solutions and ninhydrin. Pure PL were determined quantitatively by spectrophotometry [7].Total PL from A. nordmanniana seeds contained (%): phosphatidylcholine (PC), 46.7; phosphatidylinosite (PI), 21.9; phosphatidylethanolamine (PE), 18.7; and lysophosphatidylcholine (l-PC), 12.5. The results showed that the dominant component of total PL was PC. A regular distribution PC > PI > PE was observed. The qualitative and quantitative compositions of PL obtained from the raw material were identical after extraction by n-hexane and b...
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