Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi

Feng

et al. 2021

IJMS

β-pinene is a monoterpene isolated from turpentine oil and numerous other plants’ essential oils, which has a broad spectrum of biological activities. In the current work, six novel β-pinene quaternary ammonium (β-PQA) salts were synthesized and evaluated in vitro for their antifungal, antibacterial and anticancer activities. The in vitro assay results revealed that compounds 4a and 4b presented remarkable antimicrobial activity against the tested fungi and bacteria. In particular, compound 4a showed excellent activities against F. oxysporum f.sp. niveum, P. nicotianae var.nicotianae, R. solani, D. pinea and Fusicoccumaesculi, with EC50 values of 4.50, 10.92, 9.45, 10.82 and 6.34 μg/mL, respectively. Moreover, compound 4a showed the best antibacterial action against E. coli, P. aeruginosa, S. aureus and B. subtilis, with MIC at 2.5, 0.625, 1.25 and 1.25 μg/mL, respectively. The anticancer activity results demonstrated that compounds 4a, 4b, 4c and 4f exhibited remarkable activity against HCT-116 and MCF-7 cell lines, with IC50 values ranged from 1.10 to 25.54 μM. Notably, the compound 4c displayed the strongest cytotoxicity against HCT-116 and MCF-7 cell lines, with the IC50 values of 1.10 and 2.46 μM, respectively. Furthermore, preliminary antimicrobial mechanistic studies revealed that compound 4a might cause mycelium abnormalities of microbial, cell membrane permeability changes and inhibition of the activity of ATP. Altogether, these findings open interesting perspectives to the application of β-PQA salts as a novel leading structure for the development of effective antimicrobial and anticancer agents.

Section: Antifungal Activitymentioning

confidence: 99%

Design, Synthesis, Antibacterial, Antifungal and Anticancer Evaluations of Novel β-Pinene Quaternary Ammonium Salts

Feng

et al. 2021

IJMS

“…Por otra parte, el uso de fungicidas sintéticos sigue siendo la primera opción en el control de fitopatógenos de importancia agrícola (Zhu et al, 2020). Para el control de Penicillium sp.…”

Section: Antagonismo In Vitro De Levaduras De Origen Marino Hacia P Italicumunclassified

Efecto de levaduras de origen marino y ulvan en el control poscosecha de Penicillium italicum agente causal del moho azul en limón persa

et al. 2021

Penicillium italicum es el agente causal del moho azul en los cítricos. Su control es con fungicidas sintéticos, sin embargo, levaduras marinas y ulvan son una alternativa a los agro-productos sintéticos. El objetivo de este estudio fue determinar el antagonismo in vitro de levaduras hacia P. italicum y su efecto con ulvan en el control del moho azul en frutos de limón persa. Se evaluó el efecto de ulvan sobre P. italicum y levaduras. Se determinó el antagonismo in vitro por confrontación entre levadura-fitopatógeno y competencia por carbohidratos. Se evaluó la protección de frutos con levaduras y ulvan hacia P. italicum y se determinó severidad e incidencia de la enfermedad y expresión de SOD, POX y CAT. No hubo efecto de ulvan sobre los microorganismos. In vitro las levaduras inhibieron al fitopatógeno. Los carbohidratos disminuyeron con levaduras y P. italicum y se inhibió la germinación de esporas del fitopatógeno. La incidencia de P. italicum en los frutos fue disminuida por levaduras y ulvan. POX, CAT y SOD se incrementó en los frutos con levaduras y ulvan. La aplicación de levaduras marinas más ulvan puede ser una opción en el control del moho azul en frutos de limón persa.

“…Studies have indicated that natural products have unique biological functional diversity and chemical diversity, which give them unique advantages in drug molecular design [6–8] . In recent years, the derivation of molecular structures from natural products has been one of the most effective methods to develop and design drugs with unique mechanisms of action [9,10] . Amino acids are the basic constituent unit of biological macromolecular proteins, are involved in metabolism regulation and information transmission, and play crucial roles in various biological functions [11] .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and in Vitro Antifungal Mechanism of Novel Phenylalanine Derivatives

Niu

Chemistry & Biodiversity

et al. 2022

To explore novel molecules with unique mechanisms against plant pathogenic fungi, a series of phenylalanine derivatives containing a 1,3,4‐oxadiazothioether moiety were designed and synthesized. Bioassays revealed that some target compounds at 100 μg/mL exhibited excellent antifungal activities against Thanatephorus cucumeris, such as G6 (92.1 %), G10 (94.3 %), G18 (99.1 %), and G19 (98.7 %), better than that of the commercial fungicide azoxystrobin (90.6 %), and the EC50 value of G10 against T. cucumeris was 31.9 μg/mL. Further mechanism studies of T. cucumeris treated with G10 demonstrated that this compound can affect the growth of mycelia by disrupting the integrity of the membrane, and the higher the concentration of the compound is, the greater the degree of membrane integrity damage, similar to the commercial fungicide azoxystrobin. These conclusions provide important information for further mechanism studies of this series of phenylalanine derivatives.