Synthesis, characterization, and antifungal activity of novel inulin derivatives with chlorinated benzene

Abstract

a b s t r a c tA group of novel inulin derivatives containing benzene or chlorinated benzene were synthesized by reaction of chloracetyl inulin (CAIL) with the Schiff bases of 4-amino-pyridine, including (2-pyridyl)acetyl inulin chloride (PAIL), 2-[4-(2-chlorobenzylideneamino)-pyridyl]acetyl inulin chloride (2CPAIL), 2-[4-(4-chlorobenzylideneamino)-pyridyl]acetyl inulin chloride (4CPAIL), and 2-[4-(2,4-dichlorobenzylideneamino)-pyridyl]acetyl inulin chloride (2,4DCPAIL). Their antifungal activity against three kinds of phytopathogens was estimated by hypha measurement in vitro. Of all the synthesized chitosan derivatives, 2,4DCPAIL inhibited the growth of the tested phytopathogens with inhibitory indices of 67%, 47%, and 43% against Colletotrichum lagenarium (Pass) Ell.et halst, Phomopsis asparagi (Sacc.) Bubak and Fusarium oxysporum (schl.) F.sp. niveum (F. oxysporum) respectively at 1.0 mg/mL. The results indicate that all the inulin derivatives have better antifungal activity than inulin, and the inhibitory index is affected by the chlorine atom grafted to the inulin derivatives.

Synthesis, characterization, and antioxidant properties of novel inulin derivatives with amino-pyridine group

“…Peaks at 1361 cm −1 and 1319 cm −1 may be assigned to O H deformation of CH 2 OH and CH OH [33,34]. For CAIL, the reaction of chloracetyl chloride with inulin leads to a new peak at 1747 cm −1 , which can be attributed to the carbonyl (C O) [15]. The characteristic peak of secondary hydroxyl groups ( CH OH) is still at 1319 cm −1 , and the peak of O H deformation of CH 2 OH at 1361 cm −1 almost disappears.…”

“…In recent years, many studies concerning on the chemical modification of polysaccharides have been published [13,14]. Our previous work also reported the antioxidant activities and antifungal activities of inulin derivatives, which proved the chemical modification could improve the bioactivity of inulin [15][16][17].…”

“…The unreacted aminopyridines and other byproducts were extracted in a Soxhlet apparatus with acetone for two days. The products were obtained by freeze drying [15], yield: 80-90%.…”

“…The chloracetyl inulin (CAIL) was first synthesized by reaction between the C-6 hydroxyl of inulin and chloracetyl chloride. CAIL is an excellent intermediate of the project as the chlorine of CAIL can easily attack pyridine to give N-alkypyridinium salts [15,27,28]. Subsequently the pyridine containing one or two amino groups was grafted into inulin through the reaction mentioned above.…”

Synthesis, characterization, and antifungal evaluation of novel 1,2,3-triazolium-functionalized starch derivative

“…When the mycelium of fungi reached the edges of the control plate (without the presence of samples), the growth inhibition was calculated by the formula [23]:…”