Characterization of a polysaccharide having activity on the reticuloendothelial system from the stolon of Glycyrrhiza glabra var. glandulifera.

An acidic polysaccharide, named glycyrrhizan GA, was isolated from the stolon of Glycyrrhiza glabra L. var. glandulifera Reg. et Herd. It produced a single band on electrophoresis and a single peak on gel chromatography, and its molecular mass was estimated to be 85,000. Glycyrrhizan GA is composed of L-arabinose: D-galactose: L-rhamnose: D-galacturonic acid: D-glucuronic acid in the molar ratio of 22:10:1:2:1, in addition to small amounts of O-acetyl groups. Part of the hexuronic acid residues exist as methyl esters. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated that its structural features include mainly alpha-arabino-beta-3,6-galactan type structural units. Glycyrrhizan GA showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test.     

A novel neutral polysaccharide having activity on the reticuloendothelial system from the root of Glycyrrhiza uralensis

A neutral polysaccharide, named glycyrrhizan UC, was isolated from the root of Glycyrrhiza uralensis Fischer. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 69,000. Glycyrrhizan UC is composed of L-arabinose:D-galactose:D-glucose:L-rhamnose in the molar ratio of 10:30 27:1. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated its structural feature as an arabino-3,6-galacto-glucan type polysaccharide.     

An acidic polysaccharide having activity on the reticuloendothelial system from the roots and rhizomes of Saposhnikovia divaricata

An acidic polysaccharide, named saposhnikovan C, was isolated from the roots and rhizomes of Saposhnikovia divaricata Schischk. It was homogeneous as judged by electrophoresis and gel chromatography, and showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test. It is composed of D-galacturonic acid:L-rhamnose:L-arabinose:D-galactose in a molar ratio of 27:7:8:8, and its molecular mass was estimated to be 132000. About 30% of the D-galacturonic acid residues exist as the methyl esters. O-Acetyl groups were identified, and the content amounted to 3.3%. Methylation analysis, carbon-13 nuclear magnetic resonance, and controlled Smith degradation studies indicated the structural features. It has a pectin-like rhamnogalacturonan backbone with branched arabinan and galactan side chains.     

Constituents of the seed of Malva verticillata. VI. Characterization and immunological activities of a novel acidic polysaccharide

A novel acidic polysaccharide, designated as MVS-VI, was isolated from the seeds of Malva verticillata L. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 26000. It is composed of L-arabinose: D-xylose: D-galactose: D-glucose: L-rhamnose: D-galacturonic acid in the molar ratio of 30: 15: 20: 3: 2: 10, in addition to small amounts of peptide moiety. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated its structural features to have mainly acidic alpha-arabino-3,6-beta-galactan type structural units. MVS-VI showed significant reticuloendothelial system-potentiating activity in a carbon clearance test, and it possesses remarkable anti-complementary activity.     

The major pectic arabinogalactan having activity on the reticuloendothelial system from the roots and rhizomes of Saposhnikovia divaricata

The major acidic polysaccharide, named saposhnikovan A, was isolated from the roots and rhizomes of Saposhnikovia divaricata. It showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test. It is composed of L-arabinose: D-galactose: D-galacturonic acid in the molar ratio of 6:15:10, and its molecular weight was estimated to be 54000. About 35% of the D-galacturonic acid residues exist as the methyl esters. Methylation analysis, 13C-nuclear magnetic resonance, and controlled Smith degradation studies indicated that the polysaccharide has the alpha-1----4-linked D-galacturonan backbone bearing alpha-1----5-linked L-arabino-beta-3,6-branched D-galactan side chains.     

Characterization of polysaccharides having activity on the reticuloendothelial system from the rhizome of Curcuma longa

Three polysaccharides, named ukonan A, ukonan B and ukonan C, were isolated from the rhizomes of Curcuma longa L. They were homogeneous on electrophoresis and gel chromatography, and showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test. They are composed of L-arabinose: D-xylose: D-galactose: D-glucose: L-rhamnose: D-galacturonic acid in the molar ratios of 12:4:12:1:4:10 (ukonan A), 12:4:12:1:2:4 (ukonan B) and 8:3:6:14:2:3 (ukonan C), in addition to small amounts of peptide moiety. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated the structural features of ukonan B, the major one in terms of the activity. It has acidic arabino-galactan type structural units.     

An acidic polysaccharide having activity on the reticuloendothelial system from the root of Astragalus mongholicus.

An acidic polysaccharide, designated as AMon-S, was isolated from the roots of Astragalus mongholicus BUNGE. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 7.6 x 10(4). It showed significant reticuloendothelial system-potentiating activity in a carbon clearance test. It is composed of L-arabinose: D-galactose: D-galacturonic acid: D-glucuronic acid in the molar ratio of 18:18:1:1, in addition to small amounts of O-acetyl groups and peptide moiety. A part of the hexuronic acid residues exist as the methyl esters. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies enabled elucidation of its structural features and revealed mainly alpha-arabino-beta-3,6-galactan type structural units.     

Polysaccharides of Matricaria chamomilla I. Monosaccharide composition of the polysaccharide complex

Conclusions 1. A polysaccharide has been isolated from the inflorescences ofMatricaria chamomilla L. It has been established that it is composed of D-galacturonic acid (45%), D-galactose (12.2%), D-glucose (2.3%), L-rhamnose (5.3%), L-arabinose (10.2%), and D-xylose (20.8%).2. The information obtained permits the polysaccharide of the camomile to be assigned to the class of pectin substances.Academician I. P. Pavlov Ryazan' State Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 137–141, March–April, 1974.     

Plant mucilages. XLII. An anti-complementary mucilage from the leaves of Malva sylvestris var. mauritiana

A mucilage, designated as MSL-M, was isolated from the leaves of Malva sylvestris L. var. mauritiana Mill. It was homogeneous on electrophoresis and gel chromatography. Its intrinsic viscosity value in aqueous solution was 12.0, and its molecular weight was estimated to be about 6.0 x 10(6). The major constituent is an acidic polysaccharide composed of L-rhamnose: D-galactose: D-galacturonic acid: D-glucuronic acid in the molar ratio of 6:3:2:2. Methylation analysis of both the mucilage and the carboxyl-reduced derivative, carbon-13 nuclear magnetic resonance and partial hydrolysis studies indicated its main structural features. It has considerable anti-complementary activity.     

Chemical investigation of the polysaccharides of the leaves ofPlantago major L.

Summary 1. A polysaccharide has been isolated from the leaves ofPlantage major L. and its monosaccharide composition has been studied.2. It has been established that the polysaccharide investigated contains D-galacturonic acid, D-galactose, D-glucose, D-xylose, L-rhamnose, L-arabinose, a partially methylated galactose, and two unidentified monosaccharides.3. The high content of galacturonic residues (68%) in the polysaccharide enables it to be classified as a pectin.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 5, pp. 297–302, 1965     

The core structure and immunological activities of glycyrrhizan UA, the main polysaccharide from the root of Glycyrrhiza uralensis.

The controlled Smith degradation and limited hydrolysis of glycyrrhizan UA, the main phagocytosis-activating polysaccharide isolated from the root of Glycyrrhiza uralensis FISCHER, was performed. The reticuloendothelial system-potentiating, anti-complementary and alkaline phosphatase-inducing activities of glycyrrhizan UA and its degradation products were investigated. Methylation analyses of primary, secondary and tertiary Smith degradation products and of the limited hydrolysis product indicated that the core structural features of glycyrrhizan UA include a backbone chain composed of beta-1,3-linked D-galactose. All of the galactose units in the backbone carry side chains composed of mainly alpha-1,5-linked L-arabino-beta-1,6- or 1,3-linked D-galactose residues at position 6. Removal of the arabinosyl side chains caused a pronounced decrease in immunological activity.     

具有免疫促进作用的螺旋藻多糖SP-4的研究

从螺旋藻NaHCO3热水提取液中．得到四种多糖SP－1、SP－2、SP－3和SP－4，糖含量比为30：12：16：100．体外活性试验表明SP－4能促进T淋巴细胞的增殖．纸层析和高压液相色谱分析结果表明SP－4由L-鼠李糖、L-岩藻糖、L-阿拉伯糖、D-葡萄糖、D-葡萄糖胺和D-半乳糖醛酸组成，其摩尔比为4．94：2．99：2．96：1．00：1．26：2．33。IR光谱示848cm-1有明显的吸收峰，1HNMR分析在δ5．26附近有多个峰，过碘酸盐氧化和Smith降解表明SP－4分子中含有α（1→3）和α（1→4）糖苷键．     

An acidic polysaccharide having immunological activities from the rhizome of Cnidium officinale.

An acidic polysaccharide, designated as cnidirhan AG, was isolated from the rhizomes of Cnidium officinale Makino. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 5.1 x 10(4). It showed pronounced reticuloendothelial system-potentiating activity in a carbon clearance test, and had a remarkable effect on both anti-complementary and alkaline phosphatase-inducing activities. It is composed of L-arabinose: D-galactose: D-glucuronic acid in the molar ratio of 2:6:1, in addition to small amounts of O-acetyl groups. Methylation analysis, carbon-13 nuclear magnetic resonance, controlled Smith degradation and limited acid hydrolysis indicated that the core structural features of cnidirhan AG include a backbone chain composed of beta-1,3-linked D-galactose residues. Some of the galactose units in the backbone carry beta-D-galactosyl side chains at position 6. Both alpha-L-arabinosyl arabinose side chains and terminal beta-D-glucuronic acid residues are linked to the core galactan units.     

An Acidic Heteropolysaccharide from the Flowers of Malva Mauritiana L.

Abstract

An acidic heteropolysaccharide composed of L-rhamnose, D-galactose, L-arabinose, D-xylose, and uronic acids in 1.0:0.5:0.1:0.1:1.8 mole proportion was isolated from the flowers of M. mauritiana L. Structural studies of the polysaccharide involved compositional and methylation analyses of the intact and carboxyl-reduced polymers, graded acid hydrolysis as well as ¹H and ¹³C NMR spectroscopy. The results of chemical and spectroscopic analyses indicated a branched structure with the backbone made up of alternating sequences of 2- and 4-linked rhamnogalacturonan-type units with linear segments (DP = 2, 4, 12), segments bearing on O-3 of D-GalA monomeric D-GlcA randomly distributed along the chain (DP = 7, 10, 19, 31), and segments having each D-GalA substituted (DP = 15). Moreover, the results of methylation analysis indicated that about 28% of L-rhamnose residues were branched through O-4.     

Reticuloendothelial system-activating polysaccharides from rhizomes of Panax japonicus. I. Tochibanan-A and -B

From rhizomes of Panax japonicus (Araliaceae), two polysaccharides named tochibanan-A and -B, which show reticuloendothelial-potentiating activity in the carbon clearance test in mice, were isolated. The structure of tochibanan-A (molecular mass: 23,000) was elucidated as a linear beta-1,4-D-galactan. Tochibanan-B (molecular mass: 40,000) consists of D-galactose (87.1%), L-arabinose, D-glucose and D-galacturonic acid and has a beta-D-(1----4)-linked galactopyranosyl backbone possessing GalA-(1----6)-Gal, Ara-(1----5)-Ara, Gal, and Glc side chains. The structure around the branching points and the repeating unit were investigated and a possible structure of tochibanan-B is proposed.     

Structure of products of aldoses condensation with thioglycolic acid hydrazide

Condensation products of thioglycolic acid hydrazide with aldoses (L-arabinose, D-xylose, L-rhamnose, D-galactose, D-glucose, D-mannose) exist in the D₂O solution as a tautomeric mixture of α,β-pyranose form and six-membered 1,3,4-thiadiazine form present as two diastereomers.     

Chemical investigation of the polysaccharides of the leaves ofPlantago major L.

Summary 1. Pectic acid contains galacturonic acid (78–83%) and, chemically linked with it, the monosaccharides D-galactose, L-arabinose, L-rhamnose, and substance (VIII) and (IX).2. By fractionating the polysaccharide complex of the leavesof Plantago major L. on a DEAE-cellulose column it has been shown that it consists of pectic acid (80–82%), and free galactoraban (5–6%) and galactan (4–5%).Khimiya Prirodnykh Soedinenii, Vol. 1, No. 6, pp. 369–372, 1965.We have used Kertesz's nomenclature of pectic compounds [4].     

Total synthesis of lobatoside E, a potent antitumor cyclic triterpene saponin

Lobatoside E, a novel and complex cyclic triterpene saponin showing potent antitumor activities, has been synthesized for the first time, employing a highly modular approach. The synthesis, starting with oleanolic acid, D-glucose, D-galactose, L-arabinose, and L-rhamnose, requires a total of 73 steps, with the longest linear sequence of 31 steps and in 1.2% overall yield.     

Characterization of a neutral polysaccharide having activity on the reticuloendothelial system from the rhizome of Curcuma longa.

A neutral polysaccharide, named ukonan D, was isolated from the rhizome of Curcuma longa L. It produced a single band on electrophoresis and a single peak on gel chromatography, and its molecular mass was estimated to be 28,000. It showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test. Ukonan D is composed of L-arabinose: D-galactose: D-glucose: D-mannose in the molar ratio of 1:1:12:0.2, in addition to small amounts of peptide moiety. Methylation analysis, carbon-13 nuclear magnetic resonance and enzymic degradation studies indicated that its structural features include mainly both alpha-1,5-linked L-arabino-beta-3,6-branched D-galactan type and alpha-4,6-branched D-glucan type structural units. The influence of degradation with alpha-amylase followed by the elimination of glucan side chains on its immunological activity was discussed.     

Core structure of glycyrrhizan GA, the main polysaccharide from the stolon of Glycyrrhiza glabra var. glandulifera; anti-complementary and alkaline phosphatase-inducing activities of the polysaccharide and its degradation products.

The controlled Smith degradation and limited hydrolysis of glycyrrhizan GA, a representative polysaccharide with remarkable phagocytosis-enhancing activity isolated from the stolon of Glycyrrhiza glabra L. var. glandulifera Reg. et Herd. were carried out. Methylation analyses of the primary and the secondary Smith degradation products and of the limited hydrolysis product indicated that the core structural features of glycyrrhizan GA include a backbone chain composed of beta-1,3-linked D-galactose residues. Three-fifths of the galactose units in the backbone carry side chains composed of beta-1,3- and beta-1,6-linked D-galactosyl residues at position 6. Anti-complementary and alkaline phosphatase-inducing activities of the polysaccharide, periodate oxidation-reduction and the controlled Smith degradation products were investigated, and the controlled Smith degradation product showed significant activity.