The Synthesis, Fungicidal Activity, and in Silico Study of Alkoxy Analogues of Natural Precocenes I, II, and III.

This study aimed to synthesize, characterize, and explore the eco-friendly and antifungal potential of precocenes and their derivatives. The organic synthesis of the mono-O-alkyl-2,2-dimethyl 2H-1-chromene series, including the natural product precocene I, and the di-O-alkyl 2,2-dimethyl-2H-1-chromene series, including the natural 2H-1-chromenes precocenes II and III, was achieved. The synthetic compounds were subjected to spectroscopic analysis, 1HNMR,13CNMR, and mass characterization. The antifungal activity of synthesized precocenes I, II, and III, as well as their synthetic intermediates, was evaluated by the poison food technique. Precocene II (EC50 106.8 µg × mL-1 and 4.94 µg mL-1), and its regioisomers 7a (EC50 97.18 µg × mL-1 and 35.30 µg × mL-1) and 7d (EC50 170.58 × µg mL-1), exhibited strong fungitoxic activity against Aspergillus niger and Rhizoctonia solani. Some of the novel chromenes, 11a and 11b, which had never been evaluated before, yielded stronger fungitoxic effects. Finally, docking simulations for compounds with promising fungitoxic activity were subjected to structure-activity relationship analyses against the polygalactouronases and voltage-dependent anion channels. Conclusively, precocenes and their regioisomers demonstrated promising fungitoxic activity; such compounds can be subjected to minor structural modifications to yield promising and novel fungicides.

Physical Characteristics, Mineral Content, and Antioxidant and Antibacterial Activities of Punica granatum or Citrus sinensis Peel Extracts and Their Applications to Improve Cake Quality.

One-third of all food produced for human use is discarded as waste, resulting in environmental pollution and impaired food security. Fruit peels have bioactive compounds that may be used as antimicrobials and antioxidants, and the use of fruit peels is considered an alternative way to reduce environmental problems and agro-industrial waste. The aim of this study was to evaluate the phytochemical, mineral, extraction yield, total phenolic, total flavonoids, antioxidant, and antibacterial activity of several peel fruits, including Citrus sinensis (orange) and Punica granatum (pomegranate). The results revealed that pomegranate peel powder contains the highest amounts of ash, fiber, total carbohydrates, Ca, Fe, Mg, and Cu, while orange peel contains the highest amounts of moisture, protein, crude fat, P, and K. Furthermore, the aqueous and methanolic pomegranate peel extracts yielded higher total phenolic and total flavonoids than the orange peel extract. The identification and quantification of polyphenol compounds belonging to different classes, such as tannins, phenolic acids, and flavonoids in pomegranate peel and flavonoid compounds in orange peel were performed using UPLC-MS/MS. In addition, GC-MS analysis of orange peel essential oil discovered that the predominant compound is D-Limonene (95.7%). The aqueous and methanolic extracts of pomegranate peel were proven to be efficient against both gram-positive and gram-negative bacteria linked to human infections. Sponge cake substituting wheat flour with 3% pomegranate peel and 10% orange peel powder had the highest total phenolic, flavonoid compounds, and antioxidant activity as compared to the control cake. Our results concluded that pomegranate and orange peel flour can be used in cake preparation and natural food preservers.

Exogenous Putrescine Increases Heat Tolerance in Tomato Seedlings by Regulating Chlorophyll Metabolism and Enhancing Antioxidant Defense Efficiency.

Crops around the world are facing a diversity of environmental problems, of which high temperatures are proving to be the most serious threat to crops. Polyamine putrescine (Put) acts as a master growth regulator that contributes to optimal plant growth and development and increased stress tolerance. Here, the current study aimed to elucidate how Put functions in regulating chlorophyll (Chl) metabolism, oxidative stress, and antioxidant defense, as well as to characterize the expression of genes related to heat stress in tomato seedlings under such stress. The results revealed that Put treatment significantly attenuates heat-induced damage by promoting biomass production, increasing photosynthetic efficiency, and inhibiting excessive production of oxidative stress markers. Heat stress markedly decreased the Chl content in the tomato leaf and accelerated the leaf yellowing process. However, Put-treated tomato seedlings showed a higher Chl content, which could be associated with the functions of Put in elevating PBGD activity (Chl biosynthesis enzyme) and suppressing the activity of the Chl catabolic enzyme (Chlase and MDCase). Under high-temperature stress, the expression levels of the gene encoding factors involved in Chl biosynthesis and Chl catabolism were significantly down- and upregulated, respectively, and this trend was reversed in Put-treated heat-stressed seedlings. In addition, exogenous application of Put boosted the activity of antioxidant enzymes, along with the levels of expression of their encoding genes, only in plants that were heat stressed. Furthermore, the expression levels of heat-shock-related genes (HSP90, HSP70, and HsfA1) were elevated in Put-treated, high-temperature-stressed tomato seedlings. Taken together, our results indicate that Put treatment significantly increases the heat tolerance of tomato seedlings, by elevating Chl concentrations and suppressing Chl catabolic enzyme activity, modulating endogenous free PA content, increasing antioxidant defense efficiency, and upregulating the expression of heat-shock-related genes.