Characterization and cytotoxic activity of sulfated derivatives of polysaccharides from Agaricus brasiliensis

• Published in: International journal of biological macromolecules Vol. 57; pp. 265 - 272
• Main Authors: Cardozo, F.T.G.S., Camelini, C.M., Cordeiro, M.N.S., Mascarello, A., Malagoli, B.G., Larsen, I.v., Rossi, M.J., Nunes, R.J., Braga, F.C., Brandt, C.R., Simões, C.M.O.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01-06-2013
• Subjects: absorption; Agaricus; Agaricus - chemistry; Agaricus brasiliensis; Agaricus subrufescens; Animals; carbon; Cell Line, Tumor; Cercopithecus aethiops; Chemical characterization; Cytotoxic activity; cytotoxicity; Cytotoxins - chemistry; Cytotoxins - isolation & purification; Cytotoxins - pharmacology; Dose-Response Relationship, Drug; Fourier transform infrared spectroscopy; fruiting bodies; Fungal Polysaccharides - chemistry; Fungal Polysaccharides - isolation & purification; Fungal Polysaccharides - pharmacology; high performance liquid chromatography; Humans; hydrolysis; molecular weight; mycelium; neoplasm cells; nuclear magnetic resonance spectroscopy; polysaccharides; stable isotopes; Sulfated polysaccharide; sulfates; sulfur; thermal analysis; Vero Cells; Sulfated polysaccharide; Agaricus brasiliensis; Chemical characterization; Cytotoxic activity
• ISSN: 0141-8130; 1879-0003
• DOI: 10.1016/j.ijbiomac.2013.03.026

•Polysaccharides were isolated from Agaricus brasiliensis fruiting body (FR) and mycelia (MI).•The sulfated derivatives FR-S and MI-S were prepared.•FR, FR-S, MI, and MI-S were chemically characterized.•FR-S and MI-S presented promising cytotoxic activity against A549 lung tumor cells.•The cytotoxic effect was related to the presence of sulfate groups and the lower molecular weight of the sulfated polysaccharides.
Agaricus brasiliensis cell-wall polysaccharides isolated from fruiting body (FR) and mycelium (MI) and their respective sulfated derivatives (FR-S and MI-S) were chemically characterized using elemental analysis, TLC, FT-IR, NMR, HPLC, and thermal analysis. Cytotoxic activity was evaluated against A549 tumor cells by MTT and sulforhodamine assays. The average molecular weight (Mw) of FR and MI was estimated to be 609 and 310kDa, respectively. FR-S (127kDa) and MI-S (86kDa) had lower Mw, probably due to hydrolysis occurring during the sulfation reaction. FR-S and MI-S presented ~14% sulfur content in elemental analysis. Sulfation of samples was characterized by the appearance of two new absorption bands at 1253 and 810cm−1 in the infrared spectra, related to SO and CSO sulfate groups, respectively. Through 1H and 13C NMR analysis FR-S was characterized as a (1→6)-(1→3)-β-d-glucan fully sulfated at C-4 and C-6 terminal and partially sulfated at C-6 of (1→3)-β-d-glucan moiety. MI-S was shown to be a (1→3)-β-d-gluco-(1→2)-β-d-mannan, partially sulfated at C-2, C-3, C-4, and C-6, and fully sulfated at C-6 of the terminal residues. The combination of high degree of sulfation and low molecular weight was correlated with the increased cytotoxic activity (48h of treatment) of both FR-S (EC50=605.6μg/mL) and MI-S (EC50=342.1μg/mL) compared to the non-sulfated polysaccharides FR and MI (EC50>1500μg/mL).