scholarly journals Review of Oxepine-Pyrimidinone-Ketopiperazine Type Nonribosomal Peptides

Metabolites ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 246 ◽  
Author(s):  
Yaojie Guo ◽  
Jens C. Frisvad ◽  
Thomas O. Larsen

Recently, a rare class of nonribosomal peptides (NRPs) bearing a unique Oxepine-Pyrimidinone-Ketopiperazine (OPK) scaffold has been exclusively isolated from fungal sources. Based on the number of rings and conjugation systems on the backbone, it can be further categorized into three types A, B, and C. These compounds have been applied to various bioassays, and some have exhibited promising bioactivities like antifungal activity against phytopathogenic fungi and transcriptional activation on liver X receptor α. This review summarizes all the research related to natural OPK NRPs, including their biological sources, chemical structures, bioassays, as well as proposed biosynthetic mechanisms from 1988 to March 2020. The taxonomy of the fungal sources and chirality-related issues of these products are also discussed.

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3256
Author(s):  
Luis C. Chitiva-Chitiva ◽  
Cristóbal Ladino-Vargas ◽  
Luis E. Cuca-Suárez ◽  
Juliet A. Prieto-Rodríguez ◽  
Oscar J. Patiño-Ladino

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.


Proceedings ◽  
2020 ◽  
Vol 70 (1) ◽  
pp. 94
Author(s):  
Cláudia Ferreira ◽  
Rui Oliveira

Synthetic fungicides for crops protection raise environmental and human concerns due to accumulation in edible vegetables, showing significant toxicity to humans, and in soil, groundwater and rivers, affecting ecological balance. In addition, they are prone to the development of resistant strains because of the single target-based mechanism of action. Plant extracts provide attractive alternatives, as they constitute a rich source of biodegradable secondary metabolites, such as phenols, flavonoids and saponins, which have multiple modes of antifungal action and a lower probability of the development of resistant fungi. This work has the objective of identifying plant extracts with antifungal activity, aiming to contribute to food safety and sustainable agricultural practices. We selected a saponin-containing plant, Plantago major, and extracted secondary metabolites with 50% (v/v) ethanol, dried by evaporation, and dissolved in water. For antifungal activity, the phytopathogenic fungi Colletotrichum acutatum, Colletotrichum gloeosporioides, Colletotrichum godetiae, Colletotrichum nymphaeae, Diplodia corticola and Phytophthora cinnamomi were selected because they affect fruits and vegetables, such as strawberry, almond, apple, avocado, blueberry and chestnut trees. The aqueous extract was incorporated into PDA medium at different concentrations and mycelial discs were placed in the center of each Petri dish. Growth was measured as the radial mycelial growth at 3, 6, and 9 days incubation at 25 °C in the dark. The maximum growth inhibition (32.2%) was obtained against P. cinnamomi with 2000 µg/mL extract followed by C. gloeosporioides (25.7%) on the sixth day and by C. godetiae and C. nymphaeae (21.1%) on the ninth day. Results show that P. major presents antifungal activity in all phytopathogenic fungi tested and the extract can be used to protect important crops, by inhibiting the development of fungal infections and promoting food security and a sustainable agriculture.


2020 ◽  
pp. 1-7
Author(s):  
Jianfa Wang ◽  
Shuai Lian ◽  
Jun Song ◽  
Hai Wang ◽  
Xu Zhang ◽  
...  

Abstract Lipopolysaccharides (LPS) could induce milk fat depression via regulating the body and blood fat metabolism. However, it is not completely clear how LPS might regulate triglyceride synthesis in dairy cow mammary epithelial cells (DCMECs). DCMECs were isolated and purified from dairy cow mammary tissue and treated with LPS. The level of triglyceride synthesis, the expression and activity of the liver X receptor α (LXRα), enzymes related to de novo fatty acid synthesis, and the expression of the fatty acid transporters were investigated. We found that LPS decreased the level of triglyceride synthesis via a down-regulation of the transcription, translation, and nuclear translocation level of the LXRα. The results also indicated that the transcription level of the LXRα target genes, sterol regulatory element binding protein 1 (SREBP1), fatty acid synthetase (FAS), acetyl-CoA carboxylase-1 (ACC1), were significantly down-regulated in DCMECs after LPS treatment. Our data may provide new insight into the mechanisms of milk fat depression caused by LPS.


2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Paraj Shukla ◽  
Suresh Walia ◽  
Vivek Ahluwalia ◽  
Balraj S. Parmar ◽  
Muraleedharan G. Nair

Thirty known dialkanoates of ethylene, propylene and diethylene glycols were synthesized by reacting the glycols with acyl chlorides and their structures confirmed by IR, NMR and mass spectral analyses. They exhibited significant antifungal activity against two phytopathogenic fungi Rhizoctonia solani Kuehn and Sclerotium rolfsii Sacc in a dose dependent manner. Propylene glycol dipentanoate was the most active against R. solani. followed by diethylene glycol dibutanoate and ethylene glycol dibutanoate. Against S. rolfsii ethylene glycol diheptanoate was found to be most active followed by diethylene glycol diisobutanoate As compared to the standard reference benomyl (EC50 5.16 μg/mL), the potential alkanediol dialkanoates showed EC50 in the range of 33 – 60 μg/mL.


Molecules ◽  
2012 ◽  
Vol 17 (11) ◽  
pp. 13026-13035 ◽  
Author(s):  
Xin-Juan Yang ◽  
Fang Miao ◽  
Yao Yao ◽  
Fang-Jun Cao ◽  
Rui Yang ◽  
...  

2009 ◽  
Vol 23 (1) ◽  
pp. 47-60 ◽  
Author(s):  
Shunichi Matsumoto ◽  
Koshi Hashimoto ◽  
Masanobu Yamada ◽  
Teturou Satoh ◽  
Junko Hirato ◽  
...  

2020 ◽  
Author(s):  
Shraddha P. Pawar ◽  
Ambalal B. Chaudhari

Abstract Pyrrolnitrin (PRN) from rhizobacteria displays a key role in biocontrol of phytopathogenic fungi in rhizospheric soil. Therefore, different rhizospheric soils were investigated for the prevalence of PRN producer in minimal salt (MS) medium containing tryptophan (0.2 M NaCl; pH 8) using three successive enrichments. Of 12% isolates, only five bacterial strains had shown PRN secretion, screened with Thin Layer Chromatography (Rf 0.8) and antifungal activity (27 mm) against phytopathogen. The phenetic and 16S rRNA sequence revealed the close affiliation of isolates (KMB, M-2, M-11, TW3, and TO2) to Stenotrophomonas rhizophila (KY800458), Enterobacter spp. (KY800455), Brevibacillus parabrevis (KY800454), Serratia marcescens (KY800456) and Serratia nemtodiphila (KY800457). Purified compound from isolates was characterised using UV, IR, HPLC, LCMS and GCMS as PRN. However, BLASTn hit of prn gene sequences from both Serratia species showed 99% similarity with NADPH dependent FMN reductase component (prnF). The homology protein model of prnF was developed from translated sequence of S. marcescens TW3 with chromate reductase of Escherichia coli K-12. Docking with FMN and NADPH was performed. The study demonstrated the possible role of prnF NADPH dependent FMN reductases in prnD for supply of reduced flavin in rhizobacterial strain of Serratia spp. which may pave a way to understand PRN production.


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