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. 2020 Mar 30;14(1):24.
doi: 10.1186/s13065-020-00676-4. eCollection 2020 Dec.

Natural phenolic derivatives based on piperine scaffold as potential antifungal agents

Jingjing Wang  1 , Wenlong Wang  1 , Haojin Xiong  1 , Di Song  1 , Xiufang Cao  1
Affiliations

Natural phenolic derivatives based on piperine scaffold as potential antifungal agents

Jingjing Wang et al. BMC Chem. .

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 high-potential 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 1H NMR, 13C 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.

Keywords: Essential oils; Fungicidal activity; Piperine; Synthesis.

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Conflict of interest statement

Competing interestsThe authors declare no conflicts of interest.

Figures

Fig. 1
Fig. 1
Design strategy of piperine-based essential oils derivatives
Scheme 1
Scheme 1
Synthetic route for intermediates and target molecules
Fig. 2
Fig. 2
Representative 1H NMR spectra for compound 1c
Fig. 3
Fig. 3
Inhibition activity of compounds 1a, 2b, piperine and carbendazim on Phomopsis adianticola. a–e The concentration of compounds 1a, 2b, piperine and carbendazim are 12.5, 25, 50, 100, and 200 µg/mL; CK blank control
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