Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

Mar Drugs. 2018 Oct 11;16(10):380. doi: 10.3390/md16100380.

Abstract

Chemical modification is one of the most effective methods to improve the biological activity of chitin. In the current study, we modified C3-OH and C6-OH of chitin (CT) and successfully synthesized 6-amino-chitin (NCT) and 3,6-diamino-chitin (DNCT) through a series of chemical reactions. The structure of NCT and DNCT were characterized by elemental analyses, FT-IR, 13C NMR, XRD, and SEM. The inhibitory effects of CT, NCT, and DNCT against six kinds of phytopathogen (F. oxysporum f. sp. cucumerium, B. cinerea, C. lagenarium, P. asparagi, F. oxysporum f. niveum, and G. zeae) were evaluated using disk diffusion method in vitro. Meanwhile, carbendazim and amphotericin B were used as positive controls. Results revealed that 6-amino-chitin (NCT) and 3,6-diamino-chitin (DNCT) showed improved antifungal properties compared with pristine chitin. Moreover, DNCT exhibited the better antifungal property than NCT. Especially, while the inhibition zone diameters of NCT are ranged from 11.2 to 16.3 mm, DNCT are about 11.4⁻20.4 mm. These data demonstrated that the introduction of amino group into chitin derivatives could be key to increasing the antifungal activity of such compounds, and the greater the number of amino groups in the chitin derivatives, the better their antifungal activity was.

Keywords: 3,6-diamino-chitin; 6-amino-chitin; antifungal activity; chitin derivative; structure characteristics.

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Chitin / chemistry*
  • Fungi / drug effects*
  • Microbial Sensitivity Tests / methods
  • Spectroscopy, Fourier Transform Infrared / methods
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Chitin