Search Results (5)

The induction of resistance in plants involves prior activation of physiological and biochemical systems in the face of external stimuli, promoting greater tolerance to biotic stresses. Faced with the growing challenge of emerging diseases in agricultural plants and the search for more sustainable phytosanitary practices, natural substances are promising alternatives. Xylopia frutescens, known as “pindaiba-da-folha-pequena”, native to the Brazilian Cerrado and traditionally used as an antimicrobial treatment, is still little-explored in the literature and presents potentially effective compounds for the control of plant diseases. This study characterized the chemical composition and thermal stability of the X. frutescens essential oil (XEO), while evaluating its physiological and phytotoxic effects and the potential for disease control in maize and cowpea plants. The main constituents found in X. frutescens essential oil were nopinone (13.75%), spatulenol (12.94%), myrtenal (12.47%), and β-pinene (11.02%). Thermogravimetric analysis indicated that X. frutescens is highly volatile, with a large mass loss at 94.74 °C. In bioassays, the oil preserved chlorophyll levels at adequate amounts and activated several antioxidant mechanisms, but also showed a dose-dependent phytotoxic effect. In vitro assays further confirmed its antifungal activity against key phytopathogens, supporting its potential use in disease control. A general increase in the activities of the enzymes superoxide dismutase (SOD), ascorbate peroxidase (APx) and—partially—chitinase (CHIT) was observed. Catalase (CAT) decreased in both maize and cowpea plants treated with this essential oil but was higher in untreated infected plants. Such enzymatic changes suggest that the oil acts as a natural elicitor of resistance, strengthening biochemical and physiological defenses. Finally, disease severities, as measured by AUDPCs, demonstrated significant reductions in the progress of maize “Curvularia leaf spot” (Curvularia lunata) and cowpea “Web blight” (Rhizoctonia solani). The results highlight the potential of X. frutescens essential oil as an active compound stimulating defense mechanisms for applications in sustainable agricultural systems. Full article

In this study, the black fertile (BSs) and the red unfertile seeds (RSs) of the Greek endemic Paeonia clusii subsp. rhodia (Stearn) Tzanoud were studied for the first time. Nine phenolic derivatives, trans-resveratol, trans-resveratrol-4′-O-β-d-glucopyranoside, trans-ε-viniferin, trans-gnetin H, luteolin, luteolin 3′-O-β-d-glucoside, luteolin 3′,4′-di-O-β-d-glucopyranoside, and benzoic acid, along with the monoterpene glycoside paeoniflorin, have been isolated and structurally elucidated. Furthermore, 33 metabolites have been identified from BSs through UHPLC-HRMS, including 6 monoterpene glycosides of the paeoniflorin type with the characteristic cage-like terpenic skeleton found only in plants of the genus Paeonia, 6 gallic acid derivatives, 10 oligostilbene compounds, and 11 flavonoid derivatives. From the RSs, through HS-SPME and GC-MS, 19 metabolites were identified, among which nopinone, myrtanal, and cis-myrtanol have been reported only in peonies’ roots and flowers to date. The total phenolic content of both seed extracts (BS and RS) was extremely high (up to 289.97 mg GAE/g) and, moreover, they showed interesting antioxidative activity and anti-tyrosinase properties. The isolated compounds were also biologically evaluated. Especially in the case of trans-gnetin H, the expressed anti-tyrosinase activity was higher than that of kojic acid, which is a well-known whitening agent standard. Full article

A series of novel pinanyl pyrimidine amine derivatives (1e~1n) and camphoryl pyrimidine amine derivatives (2b~2f) bearing bicyclic monoterpene moieties were designed and synthesized from natural and renewable nopinone and camphor. All chemical structures of target compounds were characterized by ¹H NMR, ¹³C NMR and HRMS spectra analyses, and the antimicrobial activities were evaluated. The results indicated that most compounds showed considerable antibacterial and antifungal activities against Klebsiella pneumoniae, Streptococcus pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Methicillin-Resistant Staphylococcus aureus (MRSA), Bacillus cereus and Candida albicans. Among them, 1f showed potent antibacterial activity against all tested bacteria, 1i exhibited excellent inhibition against Streptococcus pneumoniae (1 μg/mL) and Escherichia coli (1 μg/mL), which was better than the control drug amikacin (2 μg/mL). As to antifungal activity against Candida albicans (C. albicans), compound 1l showed comparable activity (16 μg/mL) to the control drug ketoconazole. Furthermore, five active compounds with better antimicrobial activities also showed anti-inflammatory potencies against mouse mononuclear macrophages leukemia cells (RAW). Especially, 1f (IC₅₀ = 1.37 μM) and 2f (IC₅₀ = 1.87μM) are more potent than the control drug aspirin (IC₅₀ = 1.91 μM). Full article

For the first time, monoterpene trifluoromethylated β-hydroxy-benzyl-O-oximes were synthesized in 81–95% yields by nucleophilic addition of the Ruppert–Prakash reagent (TMSCF₃) to the corresponding β-keto-benzyl-O-oximes based on (+)-nopinone, (−)-verbanone and (+)-camphoroquinone. Trifluoromethylation has been determined to entirely proceed chemo- and stereoselective at the C=O rather than C=N bond. Trifluoromethylated benzyl-O-oximes were reduced to the corresponding α-trifluoromethyl-β-amino alcohols in 82–88% yields. The structure and configuration of the compounds obtained have been established. Full article

Monoterpenes are the most essential reactive biogenic volatile organic compounds. Their removal from the atmosphere leads to the formation of oxygenated compounds, such as nopinone (C₉H₁₄O), one of the most important first-generation β-pinene oxidation products that play a pivotal role in environmental and biological applications. In this study, experimental and theoretical rate coefficients were determined for the gas-phase reaction of nopinone with hydroxyl radicals (OH). The absolute rate coefficient was measured for the first time using a cryogenically cooled cell along with the pulsed laser photolysis–laser-induced fluorescence technique at 298 K and 7 Torr. The hydrogen abstraction pathways were found by using electronic structure calculations to determine the most favourable H-abstraction position. Pathway 5 (bridgehead position) was more favourable, with a small barrier height of −1.23 kcal/mol. The rate coefficients were calculated based on the canonical variational transition state theory with the small-curvature tunnelling method (CVT/SCT) as a function of temperature. The average experimental rate coefficient (1.74 × 10⁻¹¹ cm³ molecule⁻¹ s⁻¹) was in good agreement with the theoretical value (2.2 × 10⁻¹¹ cm³ molecule⁻¹ s⁻¹). Conclusively, the results of this study pave the way to understand the atmospheric chemistry of nopinone with OH radicals. Full article