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Many researchers have stated that eugenol might inhibit lipid peroxidation at the stage of initiation, propagation, or both, and many attempts have been made to elucidate the mechanism of its antioxidant activity. Nevertheless, details of its mechanism are still obscure. This study was carried out to investigate the trapping effect of eugenol on hydroxyl radical generated from L-3,4-dihydroxyphenylalanine (DOPA) in MiliQ water and the generation mechanism of the hydroxyl radical by this system which uses no metallic factor. This was studied by adding L-DOPA and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) to phosphate buffered saline (PBS) or MiliQ water, and the generation of hydroxyl radical was detected on an ESR spectrum. By this method, the effect of antioxidants was detected as a modification of ESR spectra. We found that the eugenol trapped hydroxyl radicals directly, because it had no iron chelating action, did not trap L-DOPA semiquinone radical and inhibited hydroxyl radicals with or without iron ion.

When an aqueous solution of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) was heated at 70 degrees C for 30 min, formation of DMPO-OH was observed by ESR. This DMPO-OH radical formation was suppressed under an argon atmosphere. When water was replaced with ultra-pure water for ICP-MS experiments, DMPO-OH radical formation was also diminished. Under an argon atmosphere in ultra-pure water, the intensity of the DMPO-OH signal decreased to about 1/20 of that observed under aerobic conditions with regular purified water. The addition of hydroxyl radical scavengers such as mannitol did not affect the formation of DMPO-OH, but the signal turned faint in the presence of EDTA. We suggest that DMPO reacted with dissolved oxygen to form DMPO-OH.

An acidic polysaccharide, called alisman PII, was isolated from the tuber of Alisma orientale Juzepcz. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 5.25 x 10(4). It is composed of L-arabinose:D-galactose:D-glucuronic acid in the molar ratio of 4:9:2, in addition to some of O-acetyl groups. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and controlled Smith degradation indicated that the core structural features include a backbone chain composed of beta-1,3-linked D-galactose units. Some of the galactose units in the backbone carry beta-D-galactosyl side chains at position 6. Both alpha-1,5-linked L-arabinosyl side chains and terminal beta-D-glucuronic acid residues are linked to the core galactan units. Alisman PII showed significant potentiation of the reticuloendothelial system using a carbon clearance test and also potent anti-complementary activity.

Controlled Smith degradation and limited hydrolysis of ginsenan PA, the main phagocytosis-activating polysaccharide isolated from the root of Panax ginseng C. A. Meyer, were performed. The reticuloendothelial system-potentiating and anti-complementary activities of the degradation products were investigated. Methylation analysis of the primary and secondary Smith degradation products indicated that the core structural features of ginsenan PA include a backbone chain mainly composed of beta-1,3-linked D-galactose. Almost half of the galactose units in the backbone carry side-chains composed of beta-1,6-linked D-galactosyl residues at position 6. Further 3,6-branching of D-galactose units was observed in a part of the side-chains. alpha-L-Arabinose units are connected mainly to the core galactose moieties via position 6. Removal of most of the arabinose units had a considerable effect on immunological activity.

A novel glucan, called cnidirhan SI, was isolated from the rhizome of Cnidium officinale Makino. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 1.3 x 10(4). It is composed of D-glucose alone, in addition to small numbers of O-acetyl groups. Methylation analysis, nuclear magnetic resonance and enzymic degradation studies indicated it has a high-branched glucan type structure composed of alpha-1,4-linked D-glucopyranose residues with both 3,4- and 4,6-branching points. The glucan showed significant reticuloendothelial system-potentiating activity in a carbon clearance test, as well as pronounced anti-complementary activity. This substance is the first example of a branched alpha-glucan with phagocytosis-stimulating and anti-complementary activities.

An acidic polysaccharide, called cnidirhan SIIB, was isolated from the rhizome of Cnidium officinale MAKINO. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 7.9×104. It was composed of L-arabinose, D-galactose and D-galacturonic acid in the molar ratio of 9 : 11 : 3, in addition to a few O-acetyl groups. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and controlled Smith degradation studies indicated that its structural features are composed primarily of α-L-arabino-β-3, 6- and 3, 4-branched D-galactan type units. The polysaccharide showed very pronounced reticuloendothelial system-potentiating activity in a carbon clearance test and marked anti-complementary activity.

Two acidic polysaccharides, called ginsenan S-IA and ginsenan S-IIA, were isolated from the root of Panax ginseng C. A. Meyer. They were homogeneous on electrophoresis and gel chromatography, and their molecular masses were estimated to be 5.6 x 10(4) and 1.0 x 10(5), respectively. Ginsenan S-IA is composed of L-arabinose: D-galactose: D-galacturonic acid in the molar ratio of 8:8:1, and ginsenan S-IIA is composed of L-arabinose: D-galactose: D-glucose: D-galacturonic acid in the molar ratio of 15:10:2:5, in addition to small amounts of O-acetyl groups. About a half (ginsenan S-IA) and about a quarter (ginsenan S-IIA) of the hexuronic acid residues exist as methyl esters. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and periodate oxidation studies indicated that their structural features include mainly alpha-1,5-linked L-arabino-beta-3,6-branched D-galactan type structural units. Both polysaccharides showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test and pronounced anti-complementary activity. These substances are the first examples having a relatively high content of both alpha-3,5-branched L-arabinose and beta-1,4-linked D-galactose units among the acidic arabinogalactans with activities on phagocytosis and anti-complement.

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.

Five kinds of chemically modified products were prepared from Plantago-mucilage A, the representative mucous polysaccharide isolated from the seed of Plantago asiatica L., and their reticuloendothelial system-potentiating and alkaline phosphatase-inducing activities have been investigated. Both activities were markedly enhanced when the mucilage was de-O-acetylated. The products obtained by periodate oxidation, controlled Smith degradation, and partial acid hydrolysis under the two conditions were not effective. Structural features of the partial hydrolyzates were elucidated, and it was shown that these products lost all O-acetyl groups, all xylose branches and many hexuronosyl arabinose side chains.

The structural features of ukonan C, the polysaccharide having remarkable reticuloendothelial system-potentiating activity obtained from the rhizome of Curcuma longa L., were investigated by methylation analysis, carbon-13 nuclear magnetic resonane, periodate oxidation and enzymic degradation studies. It is mainly made up of arabino-3, 6-galactan type and 4, 6-branched glucan type structural units. Degradation with α-amylase followed by the elimination of 1, 4-linked glucan side chains resulted in a marked decrease of its immunological activity.

From the hot water extract of the rhizomes of Curcuma longa , a glycan, named ukonan A, has been isolated by fractionation on DEAE-Sephadex A-25 followed by chromatography on Con A-Sepharose and Sephacryl S-300 columns. Chemical and spectroscopic studies established that the glycan possesses an α- l -arabino-3,6-β- d -galactan structure. α-1,3-Linked l -arabinopyranose, β-3,4-branched d -xylose, α-1,4-linked d -glucose, α-2,4-branched l -rhamnose and α-1,4-linked d -galacturonic acid residues were also identified as the component sugar units. The glycan showed remarkable reticuloendothelial system potentiating activity in the carbon clearance test.

An acidic polysaccharide, named eucomman A, was isolated from the dried bark of Eucommia ulmoides OLIV. It was homogeneous on electrophoresis and gel chromatography, and showed significant reticuloendothelial system-potentiating activity in a carbon clearance test. It is composed of L-arabinose : D-galactose : D-glucose : L-rhamnose : D-galacturonic acid in the molar ratio of 8 : 6 : 4 : 5 : 8 in addition to small amounts of peptide moiety. Its molecular mass was estimated to be 6.0×104. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies enabled elucidation of its structural features.

Two polysaccharides, called glycyrrhizans UA and UB, were isolated from the root of Glycyrrhiza uralensis Fischer. They were homogeneous on electrophoresis and gel chromatography, and showed reticuloendothelial system-potentiating activity in a carbon clearance test. Glycyrrhizan UA is composed of L-arabinose: D-galactose: L-rhamnose: D-galacturonic acid in the molar ratio of 20:14:1:3, and glycyrrhizan UB is composed of L-arabinose: D-galactose: D-glucose: L-rhamnose: D-galacturonic acid in the molar ratio of 12:10:1:10:20, in addition to small amounts of O-acetyl groups and peptide moiety, respectively. About 10% (glycyrrhizan UA) and 35% (glycyrrhizan UB) of the D-galacturonic acid residues exist as the methyl esters. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated their structural features.

Three aromatic glycosides, lucumin, lucuminamide and lucuminic acid, were isolated from the seeds of Calocarpum sapota MERRILL (Sapotaceae). Their structures were established by spectroscopic methods, chemical evidence, and X-ray crystallography.

A glucan, called pinellian G, was isolated from the tuber of Pinellia ternata BREIT. It was homogenous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 1.5 x 10(4). It is composed solely of D-glucose, in addition to a few O-acetyl groups. Methylation analysis, nuclear magnetic resonance and enzymic degradation studies indicated that it is a branched glucan mainly composed of alpha-1,4-linked D-glucopyranose residues with partially alpha-1,3-linked units and 4,6-branching points. The glucan showed significant reticuloendothelial system-potentiating activity in a carbon clearance test, as well as pronounced anti-complementary activity.

A glucan, called alisman SI, was isolated from the tuber of Alisma orientale Juzepcz. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was 1.1 x 10(4). It is composed solely of D-glucose. Methylation analysis, nuclear magnetic resonance and enzymic degradation studies indicated that it has a high-branched glucan type structure mainly composed of alpha-1,4-linked D-glucopyranosyl residues with partially alpha-1,6-linked units and both 3,4- and 4,6-branching points. The polysaccharide exhibited significant reticuloendothelial system-potentiating activity in a carbon clearance test, as well as a pronounced anti-complementary activity.

The controlled Smith degradation of MVS-VI, the major acidic polysaccharide having remarkable anti-complementary activity isolated from the seeds of Malva verticillata L., was performed. Methylation analysis of both the primary and the secondary Smith degradation products indicated that the core structural features of MVS-VI include a backbone chain composed of beta-1,3-linked D-galactose residues. The majority of galactose units in the backbone carry side chains composed of beta-1,3- and beta-1,6-linked D-galactosyl residues at position 6. The controlled Smith degradation products showed considerable anti-complementary activity.

Three new biphenyl ether lignans, 1, 2 and 3, were isolated from the rhizomes of Curcuma chuanyujin along with curcuminoid compounds 4, 5 and 6 and their chemical structures were determined to be 1-feruloyloxy-2-methoxycinnamic acid, 1-feruloyloxy cinnamic acid and (1-p-hydroxycinnamoyl) cinnamic acid by means of spectral evidence. The latter three known substances showed antioxidant activity.

Five new xanthones, 1,3,6-trihydroxy-5-methoxy-4-prenylxanthone (1), 1,3,5-trihydroxy-6-methoxy-2-prenylxanthone (2), 1,3,5-trihydroxy-4-(3-hydroxy-3-methylbutyl) xanthone (3), 1,3,6-trihydroxy-4-prenylxanthone (4), 3,6-dihydroxy-1,5-dimethoxyxanthone (5) and one new flavonoid, 3,5,7,4'-tetrahydroxy-2'-methoxyflavone (6) along with seven known xanthones and seven known flavonoids were isolated from the bark of Anaxagorea luzonensis A. GRAY and their chemical structures were determined by means of chemical and spectral studies. Almost all flavonoids and one xanthone (13) showed antioxidant activity.

Five new xanthones, 1,3,6-trihydroxy-5-methoxy-4-prenylxanthone (1), 1,3,5-trihydroxy-6-methoxy-2-prenylxanthone (2), 1,3,5-trihydroxy-4-(3-hydroxy-3-methylbutyl) xanthone (3), 1,3,6-trihydroxy-4-prenylxanthone (4), 3,6-dihydroxy-1,5-dimethoxyxanthone (5) and one new flavonoid, 3,5,7,4'-tetrahydroxy-2'-methoxyflavone (6) along with seven known xanthones and seven known flavonoids were isolated from the bark of Anaxagorea luzonensis A. GRAY and their chemical structures were determined by means of chemical and spectral studies. Almost all flavonoids and one xanthone (13) showed antioxidant activity.

An acidic polysaccharide, called pinellian PA, was isolated from the tuber of Pinellia ternata BRETT. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 11.8×104. Pinellian PA is composed of L-arabinose : D-galactose : L-rhamnose : D-galacturonic acid : D-glucuronic acid in the molar ratio of 5 : 15 : 1 : 3 : 3, in addition to small amounts of O-acetyl groups and peptide moieties. Reduction of carboxyl groups, methylation analysis and nuclear magnetic resonance studies show that the core structural features include a backbone chain composed of β-1, 3-linked D-galactose units. Some of the galactose units in the backbone carry β-1, 6-linked D-galactosyl side-chains at position 6. Pinellian PA produces significant potentiation of the reticuloendothelial system, as shown by a carbon clearance test, and also exhibits potent anti-complementary activity.

Two acidic polysaccharides, called rehmannan FS-I and rehmannan FS-II, were isolated from the raw root of Rehmannia glutinosa LIBOSCHITZ. They were homogeneous on electrophoresis and gel chromatography, and their molecular masses were estimated to be 5.8 x 10(4) and 6.6 x 10(4), respectively. Rehamannan FS-I is composed of L-arabinose: D-galactose: L-rhamnose: D-galacturonic acid: D-glucuronic acid in the molar ratio of 68:40:4:84:3; rehmannan FS-II is composed of L-arabinose: D-galactose: L-rhamnose: D-galacturonic acid in the molar ratio of 18:15:4:33, in addition to small amounts of O-acetyl groups. About two-thirds (rehmannan FS-I) and about one half (rehamannan FS-II) of the hexuronic acid residues exist as methyl esters. Methylation analysis of the carboxyl-reduced derivatives and nuclear magnetic resonance studies indicated that their structural features include mainly both arabino-3,6-galactan and rhamno-galacturonan type structural units. Both polysaccharides showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test.

An acidic polysaccharide, called peonan PA, was isolated from the root of Paeonia lactiflora PALLAS. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 6.0 x 10(4). Peonan PA is composed of L-arabinose: D-galactose: D-galacturonic acid in the molar ratio of 2:1:10, in addition to small amounts of O-acetyl groups and peptide moieties. About forty percent of the hexuronic acid residues in peonan PA exist as methyl esters. Reduction of carboxyl groups, methylation analysis, lithium degradation and nuclear magnetic resonance studies indicated that its main structural features involve both alpha-1,5-linked L-arabino-beta-3,6-branched D-galactan type and alpha-1,4-linked D-galacturonan type structural units. The polysaccharide exhibited remarkable reticuloendothelial system-potentiating activity in a carbon clearance test and considerable anti-complementary activity.

A novel beta-heteroglucan, called cnidirhan SIIA, was isolated from the rhizome of Cnidium officinale MAKINO. It was homogeneous on electrophoresis and gel chromatography, and its molecular mass was more than 1 x 10(7). It was composed of D-glucose, D-galactose and L-arabinose in the molar ratio of 85:5:8, in addition to small numbers of O-acetyl groups. Methylation analysis and nuclear magnetic resonance studies indicated its main structural features composed of beta-1,6-linked D-glucopyranosyl residues with both 3,6- and 4,6-branching points. In addition, it has both beta-1,4-linked L-arabinopyranosyl and beta-1,6-linked D-galactopyranosyl residues. The polysaccharide showed very pronounced reticuloendothelial system-potentiating activity in a carbon clearance test, as well as a marked anti-complementary activity.

Two acidic polysaccharides, called rehmannan SA and rehmannan SB, were isolated from the dried root of Rehmannia glutinosa Liboschitz. They were homogeneous on electrophoresis and gel chromatography, and their molecular masses were estimated to be 6.4 x 10(4) and 7.9 x 10(4), respectively. They were commonly composed of L-arabinose:D-galactose:L-rhamnose:D-galacturonic acid in the molar ratios of 10:10:1:1 (rehmannan SA) and 14:7:3:8 (rehmannan SB), in addition to small amounts of peptide moieties. About eighty percent (rehmannan SA) and about thirty percent (rehmannan SB) of the hexuronic acid residues exist as methyl esters. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and the controlled Smith degradation studies indicated the structural features of rehmannan SB, the major one in terms of the yield. It has a core structural unit of a characteristic rhamnose-rich arabino-3,6-galactan type. Both polysaccharides showed remarkable reticulo-endothelial system-potentiating activity in a carbon clearance test.

A neutral and an acidic polysaccharide, called peonan SA and peonan SB, were isolated from the root of Paeonia lactiflora Pallas. They were homogeneous on electrophoresis and gel chromatography, and their molecular masses were estimated to be 11.2 x 10(4) and 25.0 x 10(4), respectively. Peonan SA is composed of L-arabinose: D-galactose: D-glucose in the molar ratio of 1:1:28, and peonan SB is composed of L-arabinose: D-galactose: D-galacturonic acid in the molar ratio of 4:3:2, in addition to small amounts of peptide moieties. About forty percent of the hexuronic acid residues in peonan SB exist as methyl esters. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and periodate oxidation studies indicated that their structural features include mainly 3,4- and 4,6-branched alpha-D-glucan type units (peonan SA) and principally alpha-1,5-linked L-arabino-beta-3,6-branched D-galactan type structural units (peonan SB). Both polysaccharides, especially in peonan SB, showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test and considerable anti-complementary activity.

Two acidic polysaccharides, called ginsenan S-IA and ginsenan S-IIA, were isolated from the root of Panax ginseng C. A. Meyer. They were homogeneous on electrophoresis and gel chromatography, and their molecular masses were estimated to be 5.6 x 10(4) and 1.0 x 10(5), respectively. Ginsenan S-IA is composed of L-arabinose: D-galactose: D-galacturonic acid in the molar ratio of 8:8:1, and ginsenan S-IIA is composed of L-arabinose: D-galactose: D-glucose: D-galacturonic acid in the molar ratio of 15:10:2:5, in addition to small amounts of O-acetyl groups. About a half (ginsenan S-IA) and about a quarter (ginsenan S-IIA) of the hexuronic acid residues exist as methyl esters. Reduction of carboxyl groups, methylation analysis, nuclear magnetic resonance and periodate oxidation studies indicated that their structural features include mainly alpha-1,5-linked L-arabino-beta-3,6-branched D-galactan type structural units. Both polysaccharides showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test and pronounced anti-complementary activity. These substances are the first examples having a relatively high content of both alpha-3,5-branched L-arabinose and beta-1,4-linked D-galactose units among the acidic arabinogalactans with activities on phagocytosis and anti-complement.

Controlled Smith degradation of ukonan C, a phagocytosis-activating polysaccharide isolated from the rhizome of Curcuma longa L., was performed. The reticuloendothelial system-potentiating, anti-complementary and alkaline phosphatase-inducing activities of ukonan C and its degradation products were investigated. Methylation analyses of the primary and secondary Smith degradation products and of a de-arabinosylated product indicated that structural features of the arabinogalactan core of ukonan C include a backbone chain composed of beta-1,3-linked D-galactose and beta-1,4-linked D-xylose. All of the galactose units in the backbone carry side chains composed of beta-1,6-linked D-galactosyl residues with or without terminal alpha-L-arabinose units at position 3. Ukonan C showed remarkable effects on both reticuloendothelial system-potentiating and alkaline phosphatase-inducing activities. Periodate oxidation caused a decrease in or disappearance of the immunological activities, but the controlled Smith degradation product having the arabinogalactan core structure of polysaccharide showed a pronounced effect on anti-complementary activity.

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.

The controlled Smith degradation of ukonan A, a phagocytosis-activating polysaccharide isolated from the rhizome of Curcuma longa L., was performed. The reticuloendothelial system-potentiating, anti-complementary and alkaline phosphatase-inducing activities of ukonan A and its degradation products were investigated. Methylation analyses of both the primary and the secondary Smith degradation products indicated that the core structural features of ukonan A include a backbone chain mainly composed of beta-1,3-linked D-galactose, beta-1,4-linked D-xylose and alpha-1,2-linked L-rhamnose residues. All of the galactose units in the backbone carry side chains composed of alpha-L-arabino-beta-D-galactosyl or beta-D-galactosyl residues at position 6. Ukonan A has a remarkable effect on each of the three kinds of immunological activities. Periodate oxidation caused pronounced decrease or disappearance of the activities, but the controlled Smith degradation product having the core structure of polysaccharide showed considerable restoration of these activities.

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.

Three new biphenyl ether lignans, 1, 2 and 3, were isolated from the rhizomes of Curcuma chuanyujin along with curcuminoid compounds 4, 5 and 6 and their chemical structures were determined to be 1-feruloyloxy-2-methoxycinnamic acid, 1-feruloyloxy cinnamic acid and (1-p-hydroxycinnamoyl) cinnamic acid by means of spectral evidence. The latter three known substances showed antioxidant activity.

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.

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 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.

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 α-arabino-3, 6-β-galactan type structural units. MVS-VI showed significant reticuloendothelial system-potentiating activity in a carbon clearance test, and it possesses remarkable anti-complementary activity.

A main acidic polysaccharide preparation was isolated from the leaves of Malva sylvestris L. var mauritiana Mill. It is composed of L-rhamnose, D-galactose, D-galacturonic acid, and D-glucuronic acid in the molar ratio of 22:6:22:11, and it contains 7.7% peptide. It was homogeneous by electrophoresis and gel chromatography, which gave a value of 11,000 as molecular weight. The structure of the polysaccharide component was elucidated by methylation analysis and partial hydrolysis. The substance showed considerable anticomplementary activity.

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.

Two hypoglycemic principles, ganoderans B and C, isolated from the fruit bodies of Ganoderma lucidum were shown to be peptidoglycans with M ,s of 7400 and 5800, respectively. Physico-chemical and chemical studies demonstrated that the backbone and side chains of ganoderan B contain D -glucopyranosyl β-1 → 3 and β-1 → 6 linkages while those of ganoderan C contain D -glucopyranosyl β-1 → 3 and β-1 → 6 linkages and a D -galactopyranosyl α-1 → 6 linkage.

A representative mucilage, named Okra-mucilage R. was isolated from the roots of Abelmoschus esculentus MOENCH (=Hibiscus esculentus L. ; Okra). The final preparation was homogeneous as determined by ultracentrifugal analysis, cellulose acetate membrane electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 33.4. It was mainly composed of partially acetylated acidic polysaccharide, and its molecular weight was estimated to be about 1700000. The polysaccharide was composed of L-rhamnose : D-galactose : D-galacturonic acid : D-glucuronic acid : O-acetyl groups in the molar ratio of 1.1 : 1.9 : 1.0 : 1.0 : 2.0. Methylation and partial acid hydrolysis studies made it possible to deduce the structural features of the polysaccharide in the mucilage.

The O-acetyl groups in Plantago-mucilage A, the representative mucous polysaccharide isolated from the seeds of Plantago major L. var. asiatica DECAISNE (=Plantago asiatica L.), were located at position 2 of about one-fourth of L-arabinofuranosyl residues, about two-fifths of the terminal D-xylopyranosyl residues, and about one-ninth of the non-terminal D-xylopyranosyl residues. Reinvestigation of earlier methylation analysis results, showed that the mucilage possesses a main chain composed of β-1→4-linked D-xylopyranose residues having other β-D-xylopyranose units and branches composed of O-α-(D-glucopyranosyluronic acid)-(1→3)-α-L-arabinofuranose and of O-α-(D-galactopyranosyluronic acid)-(1→3)-α-L-arabinofuranose at position 3 as side chains.

A mucous polysaccharide, named Hippeastrum-H-glucomannan, was isolated from the bulbs of Hippeastrum hybridum HORT. The final preparation was homogeneous as determined by ultracentrifugal analysis, glass-fiber electrophoresis, and gel chromatography. It was composed of D-mannose and D-glucose in the molar ratio of 5 : 2, and its molecular weight was estimated to be 331000. O-Acetyl groups were identified and their content amounted to 13.2%. They were located at positions 2, 6 of some of the D-mannose units. Methylation and partial acid hydrolysis studies showed that the glucomannan is mainly composed of β-1→4-linked aldohexopyranose residues, and that it contains about eighty-three aldohexose units per six non-reducing groups on average. Both D-mannose and D-glucose units occupy non-reducing terminal positions and branching points linked through position 3.

A representative mucilage, named Althaea-mucilage RL, was isolated from the leaves of Althaea rosea CAVAILLES. The final preparation was homogeneous as determined by ultracentrifugal analysis, electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 32. 5. It was mainly composed of partially acetylated acidic polysaccharide, and its molecular weight was estimated to be about 1800000. The polysaccharide was composed of L-rhamnose : D-galactose : D-galacturonic acid : D-glucuronic acid : O-acetyl groups in the approximately molar ratio of 20 : 1 : 16 : 16 : 10. Methylation and partial hydrolysis studies made it possible to deduce the structural features of the polysaccharide moiety in the mucilage.

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.

The structure-complement activation relationship of Plantago-mucilage A, a partially O -acetylated glucuronoarabinoxylan isolated from the seed of Plantago asiatica , has been studied. The anti-complementary activity was markedly enhanced when the polysaccharide was deacetylated, but carboxyl-reduction and partial acid hydrolysis had little effect. Periodate oxidation decreased, but subsequent reduction restored, the activity; the activity of this polyalcohol was not changed in the absence of Ca 2+ . When serum was incubated with the deacetylated polymer, more marked C4 consumption was observed in the presence of Ca 2+ than with Plantago-mucilage A, but the polyalcohol did not show any C4 consumption. After incubation of the serum with the polyalcohol in the absence of Ca 2+ , a cleavage of C3 in the serum was detected by immunoelectrophoresis and by the consumption of complement when rabbit erythrocytes were used in the assay system, and these effects were much higher than for the original polysaccharide. Although the product of carboxyl-reduction did not contain O -acetyl groups, its C4 consumption was almost the same as that of Plantago-mucilage A. Thus, the O -acetyl groups in Plantago-mucilage A prevent the activation of complement via the classical pathway but the carboxyl groups are essential for the activation. The polyalcohol increases the activation of complement via the alternative pathway, but decreases the activation via the classical pathway.

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.

A neutral polysaccharide, named cinnaman AX, was isolated from the dried bark of Cinnamomum cassia BLUME. It was homogeneous on electrophoresis and gel chromatography. It is composed of L-arabinose : D-xylose in the molar ratio of 4 : 3, and its molecular weight was estimated to be about 1.0 × 106. Methylation analysis, carbon-13 nuclear magnetic resonance and controlled Smith degradation studies enabled elucidation of its structural features. It showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test.

From the hot water extract of the seeds of Malva verticillata , a polysaccharide (MVS-IIIA) has been isolated by fractionation on DEAE-Sephadex A-25 followed by chromatography on Sephacryl S-500 and Con A-Sepharose columns. Chemical and spectroscopic studies established that the polysaccharide possesses mainly an α-1,5-Iinked l -arabino-3,6-β- d -galactan structure. α-1,3-Linked l -arabinopyranose, β-1,4-linked d -xylose and α-1,4-linked d -galacturonic acid residues were also identified as the component units. The polysaccharide showed remarkable reticuloendothelial system potentiating activity in the carbon clearance test.

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.