Natural phenolic derivatives based on piperine scaffold as potential antifungal agents

Abstract

Piperine is a natural alkaloid with a wide range of biological functions. Natural phenolic compounds existed in many essential oils (EOs) are plant-derived aroma compounds with broad range of biological activities, however, their actions are slow, and they are typically unstable to light or heat, difficult to extract and so on. In order to find highpotential fungicides derived from piperine, a series of piperine-directed essential oil derivatives were designed and synthesized. The structures of all molecules were confirmed by satisfied spectral data, including 1 H NMR, 13 C NMR and ESIMS. The target compounds were screened for their potential fungicidal activities against six species of plant pathogen fungi, including Rhizoctonia solani, Fusarium graminearum, Phomopsis adianticola, Alternaria tenuis Nees, Phytophthora capsici and Gloeosporium theae-sinensis. Some of target compounds exhibited moderate and broad-spectrum activity against tested fungi compared to the parental piperine. Further studies have shown that some different concentrations of compounds have significant inhibitory activity against Alternaria tenuis Nees and Phytophthora capsici compared to commercial carbendazim, and compound 2b exhibited particularly significant broad-spectrum fungicidal activity.

Antibacterial and Antifungal Alkaloids from Asian Angiosperms: Distribution, Mechanisms of Action, Structure-Activity, and Clinical Potentials

“…typhimurium (ATCC 23564) and yielded a MIC of 3.9 µg/mL with S . aureus [ 47 , 87 ]. Piperine (200 µL of the 10 mg/mL/11 mm well) muzzled S .…”

“…aeruginosa , and C . albicans [ 87 ]. Piperine is an antibiotic potentiator that inhibits mycobacterial efflux pumps [ 50 , 87 ].…”

“…albicans [ 87 ]. Piperine is an antibiotic potentiator that inhibits mycobacterial efflux pumps [ 50 , 87 ]. Piperine very strongly constrained albicans [ 87 ] and at the concentration of 100 µg/mL suppressed R .…”

“…Piperine is an antibiotic potentiator that inhibits mycobacterial efflux pumps [ 50 , 87 ]. Piperine very strongly constrained albicans [ 87 ] and at the concentration of 100 µg/mL suppressed R . solani , Fusarium gramineum , Alternaria tenuissima , Gloeosporium theae - sinensis , Phytophthora capsici , and Phomopsis adianticola by 63.1, 53, 66.1, 76.9, 41.8, and 29.3%, respectively [ 88 ].…”

“…aeruginosa increased the susceptibility of S . aureus to rifampicin [ 87 ] and very strongly inhibited C . albicans (MIC: 3.9 µg/mL) [ 87 ].…”