https://doi.org/10.17113/ftb.57.04.19.6264

Sulfonated (1→6)-β-D-Glucan (Lasiodiplodan): Preparation, Characterization and Bioactive Properties

Gabrielle Cristina Calegari¹, Vidiany Aparecida Queiroz Santos¹, Aneli M. Barbosa-Dekker², Cleverson Busso³, Robert F. H. Dekker⁴ and Mário Antônio Alves da Cunha¹*

¹Chemistry Department, Federal University of Technology – Paraná, Via do Conhecimento, Km 1, 85503-390 Pato Branco, PR, Brazil
²Chemistry Department, State University of Londrina, Rod. Celso Garcia Cid, Km 380, 86057-970 Londrina, PR, Brazil
³Bioprocess and Biotechnology Engineering Coordination, Federal University of Technology – Paraná, Rua Cristo Rei, 19, 85902-490 Toledo, PR, Brazil
⁴Graduate Program in Environmental Engineering, Federal University of Technology – Paraná, Estr. dos Pioneiros, 3131, 86036-370 Londrina, PR, Brazil

Article history:
Received: 21 February 2019
Accepted: 5 December 2019

Key words:
sulfonation, fungal exopolysaccharides, microbiocidal activity

Summary:
Sulfonated derivatives of lasiodiplodan (LAS-S) with different degrees of substitution (1.61, 1.42, 1.02 and 0.15) were obtained and characterized by Fourier-transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and thermal and solubility analyses. Antimicrobial, antioxidant and cytotoxic potential were also assessed. The sulfonation was confirmed by FTIR analysis with specific bands at 1250 cm^–1 (S=O, strong asymmetrical stretching vibration) and at 810 cm^–1 (C-O-S, symmetrical vibration associated with the C-O-SO₃ group) in the sulfonated samples. SEM demonstrated that sulfonation promoted morphological changes on the surface of the biopolymer with heterogeneous fibrillary structures appearing along the surface following chemical modification. LAS-S showed high thermal stability, with mass loss due to oxidation at temperatures close to 460 °C. Sulfonation increased the solubility of LAS, and in addition, increased the antimicrobial activity, especially against Candida albicans (fungicidal) and Salmonella enterica Typhimurium (bacteriostatic). Native lasiodiplodan (LAS-N) showed higher OH˙ removal capacity, while LAS-S had higher ferric ion reducing antioxidant power (FRAP) potential. LAS-N and LAS-S did not demonstrate lethal cytotoxicity against wild and mutant strains of Saccharomyces cerevisiae. Samples with higher degree of substitution (1.42 and 1.61) showed lower potential to induce oxidative stress. 

*Corresponding author:  +554632202511
                                          +554632202500
                                           mcunha@utfpr.edu.br