scholarly journals Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of Plant Pathogenic Fungi

Molecules ◽  
2021 ◽  
Vol 26 (1) ◽  
pp. 207
Author(s):  
Koonchira Buaban ◽  
Weerachai Phutdhawong ◽  
Thongchai Taechowisan ◽  
Waya S. Phutdhawong

A series of tetrahydro-ß-carbolines substituted with an alkyl or acyl side chain was synthesized and screened for its antifungal activity against plant pathogenic fungi (Bipolaris oryzae, Curvularia lunata, Fusarium semitectum, and Fusarium fujikuroi). The structure activity relationship revealed that the substituent at the piperidine nitrogen plays an important role for increasing antifungal activities. In this series, 2-octyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (3g) displayed potent antifungal activities with a minimum inhibitory concentration of 0.1 μg/mL, including good inhibitory activity to the radial growth of fungus at a concentration of 100 μg/mL compared to amphotericin B.

2012 ◽  
Vol 28 (3) ◽  
pp. 317-321 ◽  
Author(s):  
Vivek K. Bajpai ◽  
Kwang-Hyun Baek ◽  
Eun-Sil Kim ◽  
Jeong-Eun Han ◽  
Myoung-Hai Kwak ◽  
...  

2016 ◽  
Vol 11 (10) ◽  
pp. 1934578X1601101
Author(s):  
Shaojun Zheng ◽  
Longbo Li ◽  
Yu Wang ◽  
Rui Zhu ◽  
Hogjin Bai ◽  
...  

A series of 24 novel derivatives of the calycanthaceous alkaloids with a tetrahydropyrroloindol-based core structure was synthesized from tryptophan in good yields. Their structures were characterized by IR, 1H NMR, and 13C NMR spectroscopy and ESI-MS. The synthesized compounds were evaluated against a wide variety of plant pathogenic fungi. Compound a9 exhibited a high degree of activity against Curvularia lunata, with 91.0% activity at a concentration of 100 μg mL−1 and with an EC50 of 44.6 μg mL−1. a7, a8, a13, and a17 exhibited high degrees of activity against Sclerotinia sclerotiorum, with a8 being the most effective with an EC50 of 38.4 μg mL−1. Compound a9 illustrated activity against Botrytis cinerea, with an EC50 of 79.5 μg mL−1. Considering the compounds evaluated, the alkyl substituents of the chain may contribute to the significant variations in fungicidal potency. The structure antifungal activity relationships are also discussed. These results will pave the way for further design, structural modification, and development of calycanthaceous alkaloids as antimicrobial agents.


2004 ◽  
Vol 157 (1) ◽  
pp. 87-90 ◽  
Author(s):  
Lynda Raynor ◽  
Anne Mitchell ◽  
Robin Walker ◽  
Robin Walker

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3671
Author(s):  
Ying-Hui Ding ◽  
Hui-Ting Wang ◽  
Sha Shi ◽  
Yao Meng ◽  
Jin-Chao Feng ◽  
...  

Four new sesquiterpenoids, named artemivestinolide D–G (1–4) and three known sesquiterpenoids (5–7), were isolated from Artemisia vestita. The structures of these new compounds were determined based on extensive spectroscopic data analyses. Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The antifeedant and antifungal activities of the isolates were evaluated against third-instar larvae of Plutella xylostella and three plant pathogenic fungi. Compounds 1–7 showed moderate antifeedant activities and compounds 1–4 and 6–7 exhibited antifungal activities.


2017 ◽  
Vol 12 (12) ◽  
pp. 1934578X1701201 ◽  
Author(s):  
Haiyu Luo ◽  
Qiuyan Zhou ◽  
Yecheng Deng ◽  
Zhiyong Deng ◽  
Zhen Qing ◽  
...  

To exploit a new source from medical plants for finding bioactive products, endophytic fungi DBR-5 identified as Nigrospora sp., was isolated from the root tubers of the traditional Chinese medicinal plant Stephania kwangsiensis Lo. The antifungal activities of the extract from its fermentation liquids were determined. The ethyl acetate extract of DBR-5 exhibited high and broad antifungal activities against plant pathogenic fungi, and showed high toxicity to Exserohilum turcicum, Bipolaris maydis, Ceratocystis paradoxa, Alternaria oleracea and Cochliobolus miyabeanus with EC50 values respectively at 0.01 mg/mL, 0.02 mg/mL, 0.03 mg/mL, 0.03 mg/mL and 0.04 mg/mL. By a bioassay guided fractionation, three antifungal secondary metabolites were isolated from liquid culture of DBR-5, and identified as griseofulvin, deoxybostrycin and austrocortirubin on the basis of spectroscopic analysis. In vitro antifungal assay showed that griseofulvin displayed significant inhibition against the hypha growth of tested plant pathogenic fungi with EC50 values ranging from 0.0013 mg/mL to 0.0202 mg/mL, and showed the highest toxicity to E. turcicum and C. paradoxa with EC50 values both at 0.0013 mg/mL. Compared with the broad spectrum fungicide carbendazim, except that the toxicity of griseofulvin to Diaporthe citri and Pestalotiopsis theae was lower, the toxicity to the other eight pathogenic fungi was much higher. The inhibitory rates of griseofulvin against spore germination of A. olerace, C. paradoxa and P. theae were 100%, 100% and 94.39% respectively, at a concentration of 0.01 mg/mL. The other two compounds deoxybostrycin and austrocortirubin exhibited only weak antifungal activities. The results indicate the potential of Nigrospora sp. DBR-5 as a source of griseofulvin and also support that griseofulvin is a natural compound with high potential bioactivity against plant pathogenic fungi.


Molecules ◽  
2020 ◽  
Vol 25 (13) ◽  
pp. 3059 ◽  
Author(s):  
Thitiphong Khamkhenshorngphanuch ◽  
Kittipat Kulkraisri ◽  
Alongkorn Janjamratsaeng ◽  
Napasawan Plabutong ◽  
Arsa Thammahong ◽  
...  

Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and C-7 positions were synthesized. The antibacterial and antifungal activities of these analogs against Staphylococcus aureus, Escherichia coli, and Aspergillus flavus were investigated. The structure-activity relationship study revealed that the length of the alkyl chain, as well as the type of substituent, has a dramatic impact on the antimicrobial activities. Particularly, the brominated analogs 3j with a nonyl side chain exhibited exceptional antifungal activities against A. flavus (half maximal inhibitory concentration (IC50) = 1.05 µg/mL), which surpassed that of the amphotericin B used as a positive control. The antibacterial activity against S. aureus, although not as potent, showed a similar trend to the antifungal activity. The data suggest that the 4-hydroxy-2-quinolone is a promising framework for the further development of new antimicrobial agents, especially for antifungal treatment.


RSC Advances ◽  
2019 ◽  
Vol 9 (64) ◽  
pp. 37376-37383
Author(s):  
Ling-Li Liu ◽  
Hong-Fei Liu ◽  
Hua-Hua Gao ◽  
Zheng-Zhong Yang ◽  
Xiao-Lan Feng ◽  
...  

The ethyl acetate extract from the liquid fermentation of S. caelestis Aw99c exhibited high and broad antifungal activities against plant pathogenic fungi.


Sign in / Sign up

Export Citation Format

Share Document