28.08.2015
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Antrodia cinnamomea (AC) is a unique fungus found inhabiting the rotten wood of Cinnamomum kanehirai.
Gel filtration chromatogram of polysaccharides AC-2 prepared from AC mycelia using a Sepharose CL-6B column (3.0 ? 82 cm).
High performance size exclusion chromatograms of antrodan detected at UV 280 nm and ELSD absorption and the molecular weight estimation.
Comparison of average molecular weight, uronic acid and glucan contents among antrodan, biobran and yeast ?-glucan. The contents of carbohydrate, protein, and monosaccharide compositions of purified antrodan from A. Effect of (a) antrodan and biobran, and (b) LPS on the cell viability of RAW 264.7 mouse macrophages. Effect of LPS on (a) NO production in RAW 264.7 mouse macrophages, (b) 24 h treatment, (c) 48 h treatment and (d) 72 h treatment with antrodan and biobran.
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A submerged liquid culture of AC has been developed and its bioproducts have been used to meet the market demand for natural fruiting bodies. In biobran, the arabinoxylan with a xylose (in its main chain) and an arabinose polymer (in its side chain) have been identified as the major components [19].
2 Average molecular weights of purified antrodan of Antrodia cinnamomea and biobran polysaccharide were determined by size exclusion chromatography. For comparison, Figure 4b and Figure 4c present the FTIR spectra of biobran and yeast ?-glucan. Antrodia camphorata, Taiwanofungus camphoratus and Ganoderma comphoratum) is a novel basidiomycete growing indigenously and uniquely in Taiwan. Likewise, yeast ?-glucan has been identified as a complex mixture of polysaccharides without any peptide moiety due to the lack of absorption at 280 nm (Figure 2c).
The calibration curve of polysaccharides MW established by using pullulan references ranging from 5.7 kDa to 788 kDa was used to analyze the prepared polysaccharide samples.
The linkages between carbohydrate and protein in the complex biomolecules of newly isolated antrodan can occur in different glycopeptide bonds arranged in amino acids and sugars. To distinguish the structural differences between polysaccharide and glycoprotein, we found that there was no polysaccharide signal appearing at 8.5 ppm in the downfield region, which is characteristic of the amide backbone of glycoproteins. Previously, we isolated polysaccharide AC-2 from AC mycelia by means of alkali extraction with subsequent acid precipitation and found it had a pronounced anti-inflammatory effect.
The components of yeast ?-glucan can be ascribed to ?-1,6-glucosidic cross-linkings between ?-1,3-glucan, mannan and chitin [20]. Taken together, these characteristics and IR absorption spectra indicated antrodan was a typical glucoxylan-protein complex.In order to determine the ?- or ?-configuration of glucose in the purified protein-bound polysaccharide antrodan, the 1H-NMR signals of antrodan (Figure 5a) were compared to those of curdlan (Figure 5b), a polysaccharide consisting of ?-d-(1>3, 1>6)-linked glucose residues [23].
Also, there was no signal appearing at 0.8 ppm (the strong methyl peak) in curdlan (Figure 5b). In this study, a novel polysaccharide named “antrodan” was obtained by further purification of AC-2 using Sepharose CL-6B column chromatography. Due to over deforestation, a limited quantity of host plants and its slow growth rate, the process for mass production of this fungus using submerged liquid culture systems is an emerging technology [2].Many bioactive components have been identified in AC, which include triterpenoids, polysaccharides, benzenoids, benzoquinone derivatives, succinic and maleic acid derivatives [3]. Biobran is a reference of pure polysaccharide and yeast ?-glucan acts as the ?-glucan reference. Antrodan was shown with moderately effective in suppressing the LPS-induced NO production (Figure 7b,c,d). The fruiting bodies of AC are enriched with triterpenoids that possess numerous biological activities, including immune-enhancing responses [4], fatigue-recovering effects [5], hepatoprotective effects [6], antioxidant, anti-inflammation and anticancer properties [3,7].


The effectiveness of antrodan on the scavenging of NO production might be attributed to its high contents of uronic acid (Table 1).
However, the most abundant and useful bioproducts obtained from the submerged liquid culture of AC mycelia are supposed to be polysaccharides, which have been widely described to potentially act as immunomodulatory products [8]. Previous studies have demonstrated that even among beta ?(1>3) or ?(1>6) glucans, slight differences in molecular weight, solubility, higher order structure like branching linkages and degree of branching, and attached proteins and lipids to backbones, higher order aggregates can result in great differences in innate immune activity [27].In animal studies, after oral administration, the specific backbone 1>3 linear ?-glycosidic chain of ?-glucans cannot be digested.
AC polysaccharides have shown various bioactivities like suppresssing the inflammatory mediator [9,10], alleviating allergic asthma [11], anti-angiogenic effects [12], modulating the immune system [13], modulating LPS-induced gene expression [14] and inhibiting tumorigenesis [15]. Most ?-glucans enter the proximal small intestine and some are captured by the macrophages.
Its FTIR confirmed the presence of ?-linkages between sugars, and intramolecular amide bonds between sugars and amino acids. Literature elsewhere has indicated that neutral polysaccharide of AC mycelia revealed promising hepatoprotective effects [16]. They are internalized and fragmented within the cells, then transported by the macrophages to the marrow and endothelial reticular system.
Its 1H-NMR spectrum showed that antrodan was a complex union of ?- and ?-glucans, which had (1>4)-linked ?-Glcp and (1>3)-linked ?-Glcp linkages to the carbohydrate chains via asparagine linked to protein site. A similar product, the protein-bound polysaccharide K (PSK, Krestin) has been approved in Japan since 1989 for use in combined chemotherapy to prolong the survival of patients with gastric cancer, colorectal cancer, and small-cell lung carcinoma [17,18].
The small ?-glucans fragments are eventually released by the macrophages and taken up by other immune cells leading to various immune responses [28]. However, documented chemical structure and biological function of AC glycoproteins are still lacking. It showed potent suppressing effect on the lipopolysaccharide-induced inflammatory responses in RAW 264.7 cell line. Considering the important and distinct health-improving bioactivity of protein-bound polysaccharides, the potential value of glycoprotein obtained from AC mycelia is worth a deeper study.In the present work, a glycoprotein, named antrodan, was obtained from the AC-2 polysaccharides fraction by further purification.
Study into the bioactivities and biological mechanisms underlying the anti-inflammatory effect of antrodan on LPS-induced acute liver injury is currently ongoing in the research group.
Meanwhile, its anti-inflammatory bioactivity was investigated with the murine cell line RAW 264.7.
To compare the bioactivity, the commercialized polysaccharide ‘Biobran’ (Daiwa Pharmaceutical Co., Tokyo, Japan), a well-known immune response modulator made from rice bran using shitake mushroom enzymes, was used as the positive control.



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