Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

Abstract

BACKGROUND Research into environmentally friendly alternatives to conventional plant protection products, to promote sustainable agriculture and healthy food, is strongly encouraged. RESULTS In this context, 20 naturally occurring terpenoids and phenolic compounds were selected and evaluated in vitro as crop protection compounds against Zymoseptoria tritici, the causal agent of Septoria tritici blotch of wheat. After selection of the most active compounds, some hemisynthetic modifications were conducted to modify their lipophilicity. These modifications led to the discovery of sesamol esters as promising antifungal agents, with IC50 around 10 μg/mL and a total absence of cytotoxicity against human cells. CONCLUSION These sesamol‐based derivatives should be selected for further evaluations in planta to validate their use as wheat crop protection agents. Moreover, the importance of a balanced hydrophily/lipophilicity ratio should be further studied. © 2021 Society of Chemical Industry

Carvacrol Derivatives as Antifungal Agents: Synthesis, Antimicrobial Activity and in Silico Studies on Carvacryl Esters

“…There are no striking differences in anticandidal potential of the homologues higher than C 3 , and from the Table 2 we can notice that there is anticandidal activity evidenced in all of the synthesized compounds (3a-y). Interestingly, Damiens et al 36 have observed and stated the importance of (a balanced) hydrophilicity/lipophilicity ratio, though in sesamol derivatives, against a phyto-pathogen fungi Zymoseptoria tritici (modulating lipophilicity proved to increase the antifungal biological activity for sesamol derivatives). The phenomena noticed in our research and in Damiens et al 36 does not have to be an isolated incident, it could also be a regularity based on subtle structural changes that would, within certain limits, by enhancing lipophilicity affect bioactivity.…”

“…Interestingly, Damiens et al 36 have observed and stated the importance of (a balanced) hydrophilicity/lipophilicity ratio, though in sesamol derivatives, against a phyto-pathogen fungi Zymoseptoria tritici (modulating lipophilicity proved to increase the antifungal biological activity for sesamol derivatives). The phenomena noticed in our research and in Damiens et al 36 does not have to be an isolated incident, it could also be a regularity based on subtle structural changes that would, within certain limits, by enhancing lipophilicity affect bioactivity. It is certain that this aspect deserves further research.…”

“…There are also a large number of reports on the synthesized esters of carvacrol and on their biological activities. 15,16,22,23,27,[29][30][31][32][33][34][35][36] Antimicrobial assays have evaluated activity of a few carvacryl esters of straight chain lower carboxylic acid homologues and diverse heteroaromatic carboxylic acids. 15,29,30,34,37 Interestingly, versus plentiful data on the synthesis and bioactivity of lower homologues, there are sporadic or no data on carvacryl esters with acid components higher than C 9 (except for C 12 reported in Bassanetti et al 34 ).…”

Understanding plant-pathogen interactions in Septoria tritici blotch infection of cereals

“…Semi-synthetic rhamnolipids (RLs) were active on Z. tritici (Platel et al, 2020). Semi-synthetic sesamol esters displayed high activity against Z. tritici (Damiens et al, 2021). Effusol, a 9,10-dehydrophenanthrene natural product from rhizomes of the plant Juncus maritimus, is active against Z. tritici (Sahli et al, 2018).…”

Profiling of Essential Oils from the Leaves of Pistacia lentiscus Collected in the Algerian Region of Tizi-Ouzou: Evidence of Chemical Variations Associated with Climatic Contrasts between Littoral and Mountain Samples

“…Nevertheless, each use was based on the fine composition of essential oils and large variability occurred. It is also known that biological activity depends on the chemical composition of the EOs [34,35]. Most of the time, the main components are important, but sometimes synergic effects due to the different, eventually minor, compounds can lead to surprising enhanced (or decreased) biological activities.…”