Sulfur-containing natural hinduchelins derivatives as potential antifungal agents against Rhizoctonia solani

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Abstract

Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. During the course of our research for highly active compounds from natural products, the natural hinduchelins A-D with typical aryl-oxazole unit have been synthesized and investigated. So, in order to develop highly potential functional molecules, a series of novel sulfur-containing aryl-oxazole compounds derived from natural hinduchelins was designed and synthesized, and their in vitro fungicidal activities against four common plant pathogenic fungi (oomycetes Phytophthora capsici, ascomycetes Sclerotinia sclerotiorum, deuteromycetes Botrytis cinerea and basidiomycetes Rhizoctonia solani) were evaluated, the results demonstrated that compounds 7b and 7c displayed good selectivity and specificity in vitro against basidiomycetes R. solani. In addition, the in vivo antifungal activities also indicated compounds 7b and 7c can protect the horsebean against infection by R. solani, and the possible mechanism of antifungal action for these compounds has also been investigated.

Graphical abstract

Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. So, in order to develop highly potential functional molecules, a series of novel sulfur-containing aryl-oxazole compounds derived from natural hinduchelins was designed and synthesized, and their bioactivity and the possible mechanism of action have been investigated.

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Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

We gratefully acknowledge the support of this work by the National Key R&D Program of China (2017YFD0200502) and the Program for Leading Talents of Hubei Academy of Agricultural Sciences, and the authors also gratefully acknowledge the partial support from Hubei Agricultural Science Innovation Centre (2019-620-000-001-27) and Innovation Group Project of Natural Science Foundation of Hubei Province (2019CFA031).

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      The general synthetic method for these carboline derivatives is described in Scheme 1, and the structures of all compounds were confirmed by their spectral analysis, as described in our previous reports (Xu et al., 2019). The in vitro fungicidal activities of these obtained carboline derivatives 4–23 against four typical plant pathogenic fungi mainly including oomycetes Phytophthora capsici, ascomycetes Sclerotinia sclerotiorum, deuteromycetes Botrytis cinerea and basidiomycetes Rhizoctonia solani were investigated using mycelium growth rate method (Wang et al., 2018; Ke et al., 2020; Huang et al., 2020), and the results were described in Table 1. According to the in vitro results indicated in Table 1, some of these carboline derivatives (such as compounds 4, 10, 14-19, and 21-23) exhibited potential antifungal activities against tested fungi.

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