Discovery of new 1,2,3,4-tetrahydro-β-carboline derivatives decorated with 3-N-substituted propionyl moiety flexibly bridged-chain as reactive oxygen species inducer for efficient antibacterial treatment

Article

Author: Zhou, Xiang ; Yang, Yike ; Su, Shanshan ; Liu, Liwei ; Fu, Xichun ; Long, Zhouqing ; Yang, Song ; Meng, Jiao ; Sun, Zhaoju

The widespread prevalence of bacterial plant diseases imposes a severe constraint on global food production and crop security. To address the growing challenge of bacterial resistance, there is an urgent demand to develop novel agrochemicals that combine high efficacy with low toxicity. In this study, a natural product modification strategy was employed to design new bactericidal candidates with an innovative cation mechanism. Tryptamine was employed as a precursor to synthesize 1,2,3,4-tetrahydro-β-carboline (THC) intermediates via the Pictet-Spengler reaction. Subsequent acylation enabled the introduction of 3-N-substituted propionyl group as flexible bridge chain through an aza-Michael reaction. The resulting racemic THC derivatives were then evaluated for their antimicrobial activity. Notably, molecule B3 demonstrated exceptional inhibitory effects against Xanthomonas oryzae pv. oryzae (Xoo, EC₅₀ = 1.32 μg/mL) and Xanthomonas axonopodis pv. citri (Xac, EC₅₀ = 2.80 μg/mL), significantly outperforming commercial agents such as bismerthiazol (BT; EC₅₀ = 40.3 μg/mL for Xoo and 89.6 μg/mL for Xac) and thiodiazole copper (TC; EC₅₀ = 58.2 μg/mL for Xoo and 37.3 μg/mL for Xac). Moreover, molecule B3 exhibited considerably higher activity than its parent molecule B (EC₅₀ = 7.27 μg/mL for Xoo and 4.89 μg/mL for Xac). In vivo assays at 200 μg/mL, B3 provided protective effects of 53.87 % against Xoo and 91.2 % against Xac, exceeding those of TC. Mechanistic investigations revealed that molecule B3 disrupted the intracellular redox balance, and result in the accumulation of reactive oxygen species (ROS) and subsequent induction of apoptosis. These findings not only identify B3 as a promising ROS inducer for bactericide development but also offer novel insights into the role of ROS in combating bacterial diseases.

01 May 2025·Journal of Chromatography A

Cellulose acetate @ functionalized UiO-66-COOH as an affordable coating sorbent for the thin-film extraction of biogenic amines followed by HPLC-MS/MS; Application to various cheese and alcohol-free beverages

Article

Author: Abbasalizadeh, Aysa ; Afshar Mogaddam, Mohammad Reza ; Sorouraddin, Saeed Mohammad ; Farajzadeh, Mir Ali

Biogenic amines are naturally occurring bioactive compounds synthesized by living organisms, playing vital roles in metabolism. High concentrations of these compounds in the human diet can lead to food poisoning. Therefore, it is crucial to measure the biogenic amines content in food samples to guarantee food safety and protect human health. In this study, a thin film dispersive solid phase extraction method combined with high-performance liquid chromatography-tandem mass spectrometry was proposed for the non-derivatization determination of some biogenic amines such as putrescine, cadaverine, histamine, tryptamine, and 2-phenylethylamine in various types of cheese samples and alcohol-free beverages. For this purpose, cellulose acetate functionalized UiO-66 with free COOH deposited on a stainless-steel mesh was effectively applied as an ultra-thin coating sorbent for the extraction and preconcentration of the target analytes. This resulted in an immense surface area containing a low sorbent amount, long lifetime and fast designing that directly extracted the desired analytes from complicated matrices. The developed design can be a reasonable alternative to electrospinning due to low energy consumption, saving time, and being a cost-effective technique. Under optimal conditions, the method provided wide linearity (5.6-1000 ng g^-1) with high coefficients of determination, satisfactory extraction recoveries, and low limits of detection (0.7-1.7 ng g^-1) and limits of quantification (1.6-5.6 ng g^-1) with good precision (relative standard deviation less than 10%). This innovative method is expected to be applicable to the majority of metal-organic frameworks, which accelerates the advancement and utilization of nanomaterials-coated stainless steel.

21 Apr 2025·ACS Agricultural Science & Technology

Biocatalyzed Synthesis of Benzoyl and Cinnamoylamides Inspired by Rice Phytoalexins

Article

Author: Pinna, Cecilia ; Molinari, Francesco ; Nespoli, Luca ; Kunova, Andrea ; Contente, Martina L. ; Martino, Piera Anna ; Dallavalle, Sabrina ; Musso, Loana ; Pinto, Andrea ; Brioschi, Giulia ; Cortesi, Paolo

Worldwide, phytopathogenic fungi, bacteria, and viruses are responsible for huge crop losses each year, threatening agricultural progress and food security and causing massive economic damages. Pyricularia oryzae represents one of the most dangerous fungal phytopathogens being the cause of rice blast, a highly destructive disease widely distributed across the world. In this critical context, good agricultural practices necessarily need to be supported using novel, effective, and sustainable agrochemicals. It is known that plants naturally counteract exogenous infections by synthesizing defense secondary metabolites, known as phytoalexins. Inspired by N-benzoyltryptamine and N-cinnamoyltryptamine, two phytoalexins found in Oryza sativa, we designed a collection of tryptamine-based derivatives. The compounds were synthesized exploiting an enzymatic approach, using Candida antarctica Lipase B (CaL-B) as a biocatalyst and tert-amyl alcohol (t-AA) as an unconventional green solvent. The activity was evaluated against a panel of different phytopathogenic fungi as well as selected Gram-negative and Gram-positive bacteria. The obtained results pave the way for novel nature-inspired products as a valuable alternative to currently available pesticides.

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Indication	Highest Phase	Country/Location	Organization	Date
Anxiety Disorders	Preclinical	United States	Alexander Shulgin Research Institute, Inc.	28 May 2024
Depressive Disorder	Preclinical	United States	Alexander Shulgin Research Institute, Inc.	28 May 2024

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