Biologically active polysaccharide from edible mushrooms: A review.

Mushrooms are renewable natural gift for humankind, furnished with unique taste, flavor and medicinal properties. For the last few decades study of mushroom polysaccharides has become a matter of great interest to the researchers for their immunomodulating, antimicrobial, antioxidant, anticancer, and antitumor properties. Molecular mass, branching configuration, conformation of polysaccharides and chemical modification are the major factors influencing their biological activities. The mechanism of action of mushroom polysaccharides is to stimulate T-cells, B-cells, natural killer cells, and macrophage dependent immune responses via binding to receptors like the toll-like receptor-2, dectin-1. The present review offers summarized and significant information about the structural and biological properties of mushroom polysaccharides, and their potential for development of therapeutic materials.

Structural characterization of a heteroglycan from an edible mushroom Termitomyces heimii.

A water soluble heteroglycan (THPS) of an average molecular weight ~1.98 × 105 Da was isolated from the aqueous extract of the fruit bodies of an edible mushroom Termitomyces heimii. Structural characterization of THPS was carried out using acid hydrolysis, methylation analysis, periodate oxidation, Smith degradation and 1D/2D NMR studies. Sugar analysis indicated the presence of glucose, mannose, galactose, and fucose in a molar ratio of nearly 6:2:2:1. The repeating unit of the THPS had a backbone consisting of four (1 â†’ 3)-ß-d-glucopyranosyl, one (1 â†’ 6)-ß-d-glucopyranosyl, two (1 â†’ 3)-α-D-manopyranosyl, and two (1 â†’ 6)-α-D-galactopyranosyl residues, out of which one (1 â†’ 3)-ß-d-glucopyranosyl residue was branched at O-6 position with terminal ß-d-glucopyranosyl residue and one (1 â†’ 6)-α-D-galactopyranosyl residue was branched at O-2 position with terminal α-L-fucopyranosyl residue.

Studies on structure and antioxidant properties of a heteroglycan isolated from wild edible mushroom Lentinus sajor-caju.

A water-soluble heteroglycan (PS-I) isolated from the aqueous extract of a wild edible mushroom Lentinus sajor-caju showed average molecular weight ∼1.79×105Da. The structure of the polysaccharide was determined using chemical and 1D/2D NMR experiments. Acid hydrolysis indicated the presence of d-glucose, d-galactose, d-mannose, and l-fucose in a molar ratio of nearly 4:4:1:1 respectively. The presence of terminal Fucp, terminal Galp, (1→3)-Glcp, (1→6)-Galp, (1→6)-Glcp, (1→4,6)-Galp, and (1→2,4)-Manp moieties were established from methylation analysis. The chemical and NMR analyses indicated that the PS-I was a heteroglycan composed of a repeating unit with backbone chain of three (1→6)-α-d-galactopyranosyl residues, two (1→6)-ß-d-glucopyranosyl residues, one (1→4)-α-d-mannopyranosyl residue, and two (1→3)-ß-d-glucopyranosyl residues where one (1→6)-α-d-galactopyranosyl residue was branched at O-4 position with terminal α-l-fucopyranosyl residue and (1→4)-α-d-mannopyranosyl residue was branched at O-2 position with terminal α-d-galactopyranosyl residue and the structure was proposed as; The PS-I is a moderate antioxidant compound which showed DPPH radical scavenging activity, hydroxyl radical scavenging activity, ABTS radical scavenging property, reducing power, and ferrous ion chelating ability.

Structural characterization and antioxidant activity of a glucan from Meripilus giganteus.

A new water soluble glucan (MGPS), with a molecular weight ∼1.48×105Da, was isolated from the fruit bodies of Meripilus giganteus by hot water extraction followed by purification through dialysis tubing cellulose membrane and sepharose 6B column chromatography. Its structural characteristics were investigated by acid hydrolysis, methylation analysis, Smith degradation and 1D/2D NMR experiments. The monosaccharide composition analysis showed that MGPS contain only glucose. The backbone of MGPS was composed of two (1→3)-ß-d-glucopyranosyl, two (1→6)-ß-d-glucopyranosyl, two (1→6)-α-d-glucopyranosyl, and one (1→4)-α-d-glucopyranosyl residues, out of which one (1→3)-ß-d-glucopyranosyl residue was branched at O-6 position with terminal α-d-glucopyranosyl residue and one (1→4)-α-d-glucopyranosyl residue branched at O-6 position with terminal ß-d-glucopyranosyl residue. In vitro antioxidant studies showed that the MGPS exhibited hydroxide radical scavenging activity (IC50=390µg/mL), superoxide radical scavenging activity (IC50=70µg/mL), and ferrous ion chelating activity (IC50=290µg/mL).

Polysaccharide of an edible truffle Tuber rufum: Structural studies and effects on human lymphocytes.

A water-soluble heteroglycan (PS-II) with average molecular weight ∼7.27×104Da, was isolated from the fruiting bodies of an edible truffle mushroom Tuber rufum (Pico) var. by hot water extraction. The structural investigation of PS-II has been carried out using acid hydrolysis, methylation analysis, periodate oxidation, and 1D/2D NMR experiments. It was composed of d-glucose, d-galactose, l-fucose in a molar ratio of nearly 4:3:1 respectively. On the basis of these experiments, the repeating unit of the PS-II was found to contain a backbone of two (1→6)-α-d-galactopyranosyl, one (1→4)-α-d-glucopyranosyl, two (1→6)-ß-d-glucopyranosyl, and one (1→4)-ß-d-glucopyranosyl residues, out of which (1→4)-α-d-glucopyranosyl residue was branched at O-2 position with terminal α-l-fucopyranosyl residue and at O-6 position with terminal α-d-galactopyranosyl residue. Ameliorative activities of the PS-II was observed at different concentrations (25, 50, 100, 200, 400µg/ml) and it maintained the redox balance as well as reduced the lipid peroxidation to protect the cell damage.

Antibacterial and DNA degradation potential of silver nanoparticles synthesized via green route.

Silver nanoparticles (AgNPs) were synthesized using a hetero polysaccharide (PS) isolated from Lentinus squarrosulus (Mont.) Singer. The polysaccharide fraction (consisting of glucose, fucose and galactose) serves the role of both reducing as well as stabilizing agent. UV-vis spectroscopy showed maximum absorbance at 407 nm due to surface plasmon resonance. High resolution transmission electron microscopy (HRTEM) exhibited that the average diameter of the nanoparticles was 2.78±1.47 nm. The XRD analysis revealed face-centered cubic (fcc) geometry of silver nanoparticles. Antibacterial activity of the AgNPs-PS conjugate was tested against multiple antibiotics resistant (MAR) Escherichia coli strain MREC33 and found that the killing was due to generation of reactive oxygen species (ROS). Internalization of AgNPs-PS conjugate along with its DNA degradation capability was demonstrated using flow cytometry. AgNPs-PS conjugates showed negligible toxicity to human RBCs. This LD50 dosage of AgNPs-PS conjugates in combination with each of the four antibiotics (ampicillin, azithromycin, kanamycin and netilmicin) to which E. coli MREC33 was resistant, showed synergistic effect to inhibit complete bacterial growth.

Studies on antioxidative and immunostimulating fucogalactan of the edible mushroom Macrolepiota dolichaula.

A water soluble fucogalactan (PS-II) of an average molecular weight ∼1.2×10(5) Da was isolated from the aqueous extract of an edible mushroom Macrolepiota dolichaula. It was composed of fucose, galactose and 3-O-methyl galactose in a molar ratio of nearly 1:4:1. Structural characterization of PS-II was carried out using total hydrolysis, methylation analysis, Smith degradation, and 1D/2D NMR experiments. These results indicated that the proposed repeating unit of the PS-II had a backbone chain consisting of four (1→6)- linked α-d-Galp residues, one residue methylated at O-3, and another one substituted at O-2 by (1→2)-α-d-Galp residue, which is terminated with a α-l-Fucp moiety. The PS-II exhibited the antioxidant properties in different in vitro test systems, and also showed in vitro macrophage activation in RAW 264.7 cell line as well as splenocyte and thymocyte activation in mouse cell culture medium.

Heteroglycan of an edible mushroom Termitomyces clypeatus: structure elucidation and antioxidant properties.

A water-soluble heteroglycan (PS) of an average molecular weight ∼1.98 ×10(5) Da was isolated from the aqueous extract of an edible mushroom Termitomyces clypeatus (R. Heim). The structure of the polysaccharide (PS) was established using total hydrolysis, methylation analysis, Smith degradation, and 1D/2D NMR experiments. Total hydrolysis indicated the presence of d-glucose, d-galactose, d-mannose, and l-fucose in a molar ratio of 4.10:1.95:1.0:0.95, respectively. The chemical and NMR analysis indicated the presence of a repeating unit with a backbone consisting of one each of the residues (1→3)-α-d-galactopyranosyl, (1→3)-α-d-mannopyranosyl, (1→3)-α-d-glucopyranosyl, (1→3)-ß-d-glucopyranosyl, (1→6)-ß-d-glucopyranosyl, and (1→6)-α-d-galactopyranosyl, respectively. The (1→3)-α-d-mannopyranosyl residue was found branched at O-2 with terminal α-l-fucopyranosyl moiety and (1→3)-ß-d-glucopyranosyl residue was branched at O-6 with terminal α-d-glucopyranosyl residue. The PS exhibited antioxidant properties.

Structural elucidation and biological studies of a novel exopolysaccaride from Klebsiella pneumoniae PB12.

An exopolysaccharide (KNPS) of an average molecular weight ∼1.8×10(5) Da was isolated from the culture medium of Klebsiella pneumoniae PB12. Structural characterization of KNPS was carried out using sugar and methylation analysis, Smith degradation and 1D/2D NMR experiments. Sugar analysis showed that the KNPS composed of arabinose, galactose, 3-O-methyl-galctose and glucose in a molar ratio of nearly 4:3:1:1. The proposed repeating unit of the KNPS has a backbone chain consisting of two (1→6)-galactopyranosyl residues, two (1→5)-arabinofuranosyl residues, one (1→6)-glucopyranosyl residue and one (1→3)-arabinopyranosyl residue, out of which one (1→6)-galactopyranosyl residue was branched at O-2 position with a (1→2)-linked-galactopyranosyl residue terminated with non reducing arabinofuranosyl residue and one (1→5)-arabinofuranosyl residue branched at O-3 position with non reducing end 3-O-Me-galactopyranosyl residue. KNPS was found non-toxic toward human lymphocyte up to the dosage of 100 µg/ml. KNPS enhanced malondialdehyde (MDA), reactive oxygen species (ROS), and have the potential to alter the ratio of oxidized glutathione (GSSG) and reduced glutathione (GSH) levels in the cellular system.

Structural, immunological, and antioxidant studies of ß-glucan from edible mushroom Entoloma lividoalbum.

A water soluble ß-glucan having molecular weight ∼2×10(5)Da was isolated from hot water extract of the fruit bodies of an edible mushroom Entoloma lividoalbum (Kühner & Romagn) Kubicka. This polysaccharide (ELPS) contains (1→3,6)-ß-D-Glcp, (1→3)-ß-D-Glcp, (1→6)-ß-D-Glcp, and terminal ß-D-Glcp moieties in a molar ratio of nearly 1:1:3:1. Chemical and spectroscopic analysis showed that the backbone of glucan consists of three (1→6)-ß-D-glucopyranosyl and two (1→3)-ß-D-glucopyranosyl residues, out of which one (1→3)-ß-D-glucopyranosyl moiety was branched at O-6 with a terminal ß-D-glucopyranosyl residue. This ß-glucan exhibited macrophage, splenocyte, and thymocyte stimulations. It possesses promising antioxidant activities as evidenced from its hydroxyl and superoxide radical scavenging activities and reducing properties.

Heteroglycan of an edible mushroom Entoloma lividoalbum: structural characterization and study of its protective role for human lymphocytes.

A water soluble heteroglycan (PS-II) of an average molecular weight ∼5.2×10(4)Da was isolated from the alkaline extract of an edible mushroom Entoloma lividoalbum (Kühner & Romagn) Kubicka. Structural characterization of PS-II was carried out using sugar and methylation analysis, periodate oxidation study, and 1D/2D NMR experiments. Sugar analysis indicated the presence of glucose, mannose, galactose, and fucose in a molar ratio of nearly 5:1:2:1. The repeating unit of the PS-II had a backbone consisting of two (1→3)-ß-d-glucopyranosyl, one (1→6)-ß-d-glucopyranosyl, one (1→2)-α-L-fucopyranosyl, one (1→6)-α-d-glucopyranosyl, and two (1→6)-α-d-galactopyranosyl residues, out of which one (1→3)-ß-d-glucopyranosyl residue was branched at O-6 position with terminal ß-d-glucopyranosyl residue and one (1→6)-α-d-galactopyranosyl residue was branched at O-2 position with terminal ß-d-mannopyranosyl residue. PS-II showed ameliorative activities at different concentrations (50, 100, 200, 400µg/ml) and maintained the redox balance as well as reduced the lipid peroxidation to protect the cell destruction.

A partially methylated mannogalactan from hybrid mushroom pfle 1p: purification, structural characterization, and study of immunoactivation.

A new water-soluble heteropolysaccharide (PS-II) with apparent molecular weight ∼1.65×10(5) Da, was isolated from the fruiting bodies of hybrid mushroom pfle 1p by hot aqueous extraction. It is composed of d-mannose, d-galactose, and 3-O-Me-d-galactose in a molar ratio of 1.0:0.99:1.1. The structural investigation of PS-II has been carried out using acid hydrolysis, methylation analysis, periodate oxidation study, and 1D/2D NMR experiments. Based on the results of these experiments, it was established that PS-II contained a main chain of (1→6) linked α-d-galactopyranosyl residues, one of which was substituted at C-2 by a terminal mannopyranosyl residue and also methylated at C-3 position. This heteropolysaccharide (PS-II) exhibited macrophage activation by NO production as well as in vitro splenocyte and thymocyte stimulation.

Structure elucidation and antioxidant properties of a soluble ß-D-glucan from mushroom Entoloma lividoalbum.

A water soluble branched ß-D-glucan (PS-I) with an average molecular weight ~2.1×10(5) Da was isolated from alkaline extract of the fruit bodies of the edible mushroom Entoloma lividoalbum (Kühner & Romagn) Kubicka which consists of terminal ß-D-glucopyranosyl, (1→3)-ß-D-glucopyranosyl, (1→6)-ß-D-glucopyranosyl, and (1→3,6)-ß-D-glucopyranosyl moieties in a molar ratio of nearly 1:3:2:1. The structure of PS-I was elucidated using acid hydrolysis, methylation analysis, periodate oxidation study, partial hydrolysis, and 1D/2D NMR experiments. The repeating unit of the polysaccharide (PS-I) contains a backbone chain of three (1→6)-ß-D-glucopyranosyl residues, one of which was branched at O-3 position with the side chain consisting of three (1→3)-ß-D-glucopyranosyl and a terminal ß-D-glucopyranosyl residues. Total antioxidant capacity of 1mg PS-I was measured and found equivalent to 70±15 µg of ascorbic acid. The PS-I was found to possess hydroxyl and superoxide radical-scavenging activities with EC50 values of 480 and 150 µg/mL, respectively. The reducing power of PS-I was determined 0.5 at 480 µg/mL.

Antioxidant and immunostimulant ß-glucan from edible mushroom Russula albonigra (Krombh.) Fr.

A water soluble ß-glucan (PS) with an average molecular weight ∼1.95 × 10(5)Da was isolated from the alkaline extract of ectomycorrhizal edible mushroom, Russula albonigra (Krombh.) Fr. and found to consist of terminal, (1 → 3)-, (1 → 6)-, and (1 → 3,6)-linked ß-D-glucopyranosyl moieties in a ratio of nearly 1:2:2:1. The structure of this PS was elucidated on the basis of total hydrolysis, methylation analysis, Smith degradation, partial hydrolysis, and 1D/2D NMR experiments. On the basis of these experiments, the repeating unit of the PS was found to contain a backbone of three (1 → 6)-ß-D-glucopyranosyl residues, one of which was branched at O-3 position with the side chain consisting of two (1 → 3)-ß-D-glucopyranosyl and a terminal ß-D-glucopyranosyl residue. This PS showed in vitro macrophage activation by NO production as well as splenocytes and thymocytes proliferation. Moreover, it also exhibited potent antioxidant activities.

Structural characterization of an immunoenhancing glucan isolated from a mushroom Macrolepiota dolichaula.

A water soluble branched glucan (PS-I) was isolated from aqueous extract of the fruit bodies of an edible mushroom Macrolepiota dolichaula, having average molecular weight ~2.02×10(5) Da. The structure of this PS-I was determined using total hydrolysis, methylation analysis, Smith degradation, partial hydrolysis, and 1D/2D NMR experiments. Total hydrolysis and methylation analysis results showed the presence of (1→3, 6)-, (1→6)-, (1→4)-, (1→3)-linked and terminal ß-D-glucopyranosyl residues in a relative proportion of nearly 1:2:1:1:1. All the chemical and NMR results indicated that the PS-I was a branched glucan, and the repeating unit of this glucan consisted of a backbone chain of three (1→6)-linked-ß-D-glucopyranosyl residues where one of the backbone residues is branched at O-3 with (1→3)- moiety which is further attached to another (1→4)- residue and terminated with a non-reducing ß-D-glucopyranosyl residue. The PS-I exhibited in vitro macrophage activation in RAW 264.7 cell line as well as splenocyte and thymocyte activation in mouse cell culture medium.

A heteropolysaccharide from an edible hybrid mushroom pfle 1p: structural and immunostimulating studies.

A water-soluble heteropolysaccharide (PS-I) having molecular weight ~2.1×10(5) Da was isolated from hot aqueous extract of the fruit bodies of hybrid mushroom pfle 1p. The hybrid mushroom pfle 1p was obtained through intergenic protoplast fusion between Pleurotus florida and Lentinula edodes. The heteropolysaccharide contained D-glucose, D-galactose, and D-mannose in a molar ratio of nearly 4:2:1. The structural investigation of PS-I has been carried out using sugar and methylation analyses as well as 1D/2D NMR experiments ((1)H, (13)C, DEPT-135, DQF-COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC). Based on the results of these experiments, the repeating unit of the PS-I was established as: [structure: see text]. PS-I showed in vitro macrophage activation by NO production and also stimulated splenocytes and thymocytes.

Structural elucidation of an immunoenhancing heteroglycan isolated from Russula albonigra (Krombh.) Fr.

A water soluble heteroglycan (PS-II) of average molecular weight ∼1.45 × 10(5)Da was isolated from the aqueous extract of an ectomycorrhizal edible mushroom, Russula albonigra (Krombh.) Fr. Structural characterization of PS-II was carried out using acid hydrolysis, methylation analysis, periodate oxidation, and 1D/2D NMR studies. Structural analysis revealed that PS-II was composed of terminal 2-O-methyl-Fucp, terminal Manp, (1→2)-Fucp, (1→3)-Glcp, (1→3,4)-Glcp, (1→6)-Galp, and (1→2,6)-Galp residues in a relative proportion of approximately 1:1:1:1:1:1:1. The proposed repeating unit of the PS-II had a backbone consisting of two (1→3)-ß-d-glucopyranosyl, two (1→6)-α-d-galactopyranosyl, and one (1→2)-α-l-fucopyranosyl residues, out of which one (1→3)-ß-d-glucopyranosyl residue was branched at O-4 position with terminal 2-O-methyl-α-l-fucopyranosyl and one (1→6)-α-d-galactopyranosyl residue was branched at O-2 position with terminal α-d-mannopyranosyl residue. This PS-II showed in vitro macrophage activation by NO production as well as splenocytes and thymocytes proliferation.

Structural characterization of an immunoenhancing heteroglycan of a hybrid mushroom (pfls1h) of Pleurotus florida and Lentinus squarrosulus (Mont.) Singer.

An immunostimulating water-soluble heteroglycan (PS-II) was isolated from an aqueous extract of the fruit bodies of a hybrid mushroom, pfls1h produced by intergeneric protoplast fusion between Pleurotus florida and Lentinus squarrosulus (Mont.) Singer. Structural characterization of PS-II was carried out using sugar analysis, methylation experiment, periodate oxidation and 1D/2D NMR studies. Sugar analysis indicated the presence of glucose, mannose and galactose in a molar ratio of 1:1:2. Methylation analysis revealed that PS-II was composed of (1→6)- and (1→2,4,6)-α-D-galactopyranosyl, terminal ß-D-mannopyranosyl and terminal ß-D-glucopyranosyl residues in a relative proportion of approximately 1:1:1:1. On the basis of chemical analysis and NMR studies, the structure of the repeating unit of the heteroglycan was established to consist of a backbone chain of two (1→6)-α-D-galactopyranosyl residues, one of which is branched at O-2 with terminal ß-D-Manp and at O-4 with terminal ß-D-Glcp. This heteroglycan (PS-II) showed in vitro splenocyte, thymocyte and macrophage activations.

Structural elucidation of a biologically active heteroglycan isolated from a hybrid mushroom of Pleurotus florida and Lentinula edodes.

A water soluble heteroglycan isolated from hot aqueous extract of fruit bodies of an edible hybrid mushroom Pfle1r of Pleurotus florida and Lentinula edodes consists of d-glucose, d-mannose, and d-galactose residues in a molar ratio of nearly 1:1:1. This polysaccharide showed macrophage, splenocyte, and thymocyte activation. On the basis of sugar hydrolysis, methylation, periodate oxidation study, and NMR studies (1H, 13C, DEPT-135, TOCSY, DQF-COSY, NOESY, ROESY, HSQC, and HMBC), the structure of the repeating unit of the polysaccharide was established as: -->6)-α-D-Galp-(1-->6)-α-D-Glcp-(1-->2<--1ß-D-Manp.