New diphenyl ethers from a fungus Epicoccum sorghinum L28 and their antifungal activity against phytopathogens

Zhu, Jiachen; Lu, Haihong; Liu, Shengquan; Ding, Weijia; Li, Jiazhong; Xiong, Yong; Li, Chunyuan

doi:10.1016/j.bioorg.2021.105232

Cited by 8 publications

(8 citation statements)

References 25 publications

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“…In summary, two undescribed p-terphenyl derivatives, asperterphenylcins A-B (1-2), and two undescribed diphenyl ether derivatives, asperdiphenylcins A-B (3-4), together with three previously described p-terphenyl derivatives-4 ′′ -deoxyterprenin ( 5), terphenyllin (6), and 3 ′′ -hydroxyterphenyllin (7)-were obtained from the crude EtOAc extract of a solid-rice culture of a marine sponge-derived fungus A. candidus HM5-4. Bioassays were used to evaluate its cytotoxic activity, α-glucosidase inhibitory activity and antifungal activity.…”

Section: Discussionmentioning

confidence: 94%

“…Over 250 p-terphenyl derivatives have been identified, mainly from actinomyces, mosses and macrofungi [1]. In most cases, these secondary metabolites exhibit extensive biological activity, such as antimicrobial [5,6], cytotoxicity [7,8], free radical scavenging [9,10], phosphodiesterase inhibitory [11] and α-glucosidase inhibitory activities [12]. The unique marine environment, with its high pressure, low temperature and high salinity, leads to the generation of secondary metabolites with different marine fungi biological activities, which are an important source of natural products with pharmacological effects [13].…”

Section: Introductionmentioning

confidence: 99%

“…For this reason, in the process of searching for new bioactive natural products from marine-derived fungi [17][18][19][20], we carried out chemical studies on A. candidus, a fungus from a marine sponge which was collected from the coast of Lingao County, Hainan Province. Two undescribed p-terphenyl derivatives, asperterphenylcins A-B (1-2), and two undescribed diphenyl ether derivatives, asperdiphenylcins A-B (3-4), together with three previously described p-terphenyl derivatives-4 ′′ -deoxyterprenin (5), terphenyllin (6), and 3 ′′ -hydroxyterphenyllin (7; Figure 1)-were isolated from the crude EtOAc extract of a solid-rice culture of the marine sponge-derived fungus A. candidus HM5-4. Based on the extensive biological activity of p-terphenyls, all compounds were screened for antifungal, cytotoxic and α-glucosidase inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

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p-Terphenyl and Diphenyl Ether Derivatives from the Marine-Derived Fungus Aspergillus candidus HM5-4

Zeng,

Wang,

Peng

et al. 2023

Marine Drugs

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Two undescribed p-terphenyl derivatives, asperterphenylcins A–B (1–2), and two undescribed diphenyl ether derivatives, asperdiphenylcins A–B (3–4), together with three previously described p-terphenyl derivatives—4″-deoxyterprenin (5), terphenyllin (6), and 3″-hydroxyterphenyllin (7)—were obtained from the solid-rice culture of the marine-derived fungus Aspergillus candidus HM5-4, which was isolated from sponges from the South China Sea. Their structures were elucidated by HRESIMS data and NMR spectroscopic analysis. Compound 1 showed a strong inhibitory effect on Neoscytalidium dimidiatum, with an inhibition circle diameter of 31.67 ± 2.36 mm at a concentration of 10.0 µg/disc. Compounds 5 and 7 displayed cytotoxic activity against human chronic myeloid leukemia cells (K562), human liver cancer cells (BEL-7402), human gastric cancer cells (SGC-7901), human non-small cell lung cancer cells (A549) and human HeLa cervical cancer cells, with IC50 values ranging from 3.32 to 60.36 µM, respectively. Compounds 2, 6 and 7 showed potent inhibitory activity against α-glucosidase, with IC50 values of 1.26 ± 0.19, 2.16 ± 0.44 and 13.22 ± 0.55 µM, respectively.

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Section: Discussionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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p-Terphenyl and Diphenyl Ether Derivatives from the Marine-Derived Fungus Aspergillus candidus HM5-4

Zeng,

Wang,

Peng

et al. 2023

Marine Drugs

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“…(328EF), and H. insecticola (33EF), at physiological stress conditions. Previous studies have described species of these genera as producers of secondary metabolites and antagonists to phytopathogens (e.g., Breinholt et al, 1997;Giridharan et al, 2014;Braga et al, 2018;Puri et al, 2018;Zhu et al, 2021); however, when we forced the interaction of these species with G. max plants, biotic stress responses were observed in the plants.…”

Section: The Hydroponic System Allows the Association Of Phosphate Solubilization With Growth Promotion And Improved Photosynthetic And Amentioning

confidence: 93%

Efficiency of the Hydroponic System as an Approach to Confirm the Solubilization of CaHPO4 by Microbial Strains Using Glycine max as a Model

et al. 2021

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The sustainable development of agriculture can be stimulated by the great market availability of bio-inputs, including phosphate-solubilizing microbial strains. However, these strains are currently selected using imprecise and questionable solubilization methodologies in solid or liquid media. We hypothesized that the hydroponic system could be a more efficient methodology for selecting phosphate-solubilizing strains as plant growth promoters. This methodology was tested using the plant Glycine max as a model. The growth-promoting potential of the strains was compared with that of the Biomaphos® commercial microbial mixture. The obtained calcium phosphate (CaHPO4) solubilization results using the hydroponic system were inconsistent with those observed in solid and liquid media. However, the tests in liquid medium demonstrated poor performances of Codinaeopsis sp. (328EF) and Hamigera insecticola (33EF) in reducing pH and solubilizing CaHPO4, which corroborates with the effects of biotic stress observed in G. max plants inoculated with these strains. Nevertheless, the hydroponic system allowed the characterization of Paenibacillus alvei (PA12), which is also efficient in solubilization in a liquid medium. The bacterium Lysinibacillus fusiformis (PA26) was the most effective in CaHPO4 solubilization owing to the higher phosphorus (P) absorption, growth promotion, and physiological performance observed in plants inoculated with this bacterium. The hydroponic method proved to be superior in selecting solubilizing strains, allowing the assessment of multiple patterns, such as nutritional level, growth, photosynthetic performance, and anatomical variation in plants, and even the detection of biotic stress responses to inoculation, obtaining strains with higher growth promotion potential than Biomaphos®. This study proposed a new approach to confirm the solubilizing activity of microorganisms previously selected in vitro and potentially intended for the bio-input market that are useful in P availability for important crops, such as soybeans.

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“…During our previous work to discover antimicrobial agents from microorganisms, [20][21][22] the investigation of metabolites of a fungus P. boydii XFQ03 purified from P. canaliculata led to the purification and identification of pseudallecin A (PA) (Figure 1) and pseudallecin B. The composition and structure of PA were characterized in Figure S1-S7.…”

Section: Introductionmentioning

confidence: 99%

Assessment of the Binding of Pseudallecin A to Human Serum Albumin with Multi‐Spectroscopic Analysis, Molecular Docking and Molecular Dynamic Simulation

Li,

Chen,

Qin

et al. 2023

Chemistry & Biodiversity

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The binding of pseudallecin A (PA), a potential antibiotic with strong inhibitory activities against Gram‐positive Escherichia coli and Gram‐negative Staphylococcus aureus, to human serum albumin (HSA) was explored. The interaction between them was assessed by multi‐spectroscopic analysis, binding site competitive analysis, molecular docking and molecular dynamic simulation, showing the results as follows: PA effectively quenched the innate fluorescence of HSA by a static quenching process, formed a complex at a molar ratio of approximately 1:1 and performed an effective non‐radiative energy transfer; the binding of PA to HSA was a spontaneous exothermic reaction driven by enthalpy with strong affinity and had a slight effect on the conformation of HSA; PA bound at site Ⅲ of HSA and hydrogen bonds were the major binding forces to maintain the stability of the PA‐HSA complex. Molecular dynamic simulation was performed to calculate the root mean square deviation (RMSD), root mean square fluctuation (RMSF) and radius of gyration (Rg) for this complex and effectively supported the spectroscopic outcome. These results meant that the delivery and distribution of PA as a water‐insoluble molecule can be efficiently accomplished via HSA in human blood and, it has a good potential for future drug application and pharmacological development.

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New diphenyl ethers from a fungus Epicoccum sorghinum L28 and their antifungal activity against phytopathogens

Cited by 8 publications

References 25 publications

p-Terphenyl and Diphenyl Ether Derivatives from the Marine-Derived Fungus Aspergillus candidus HM5-4

p-Terphenyl and Diphenyl Ether Derivatives from the Marine-Derived Fungus Aspergillus candidus HM5-4

Efficiency of the Hydroponic System as an Approach to Confirm the Solubilization of CaHPO4 by Microbial Strains Using Glycine max as a Model

Assessment of the Binding of Pseudallecin A to Human Serum Albumin with Multi‐Spectroscopic Analysis, Molecular Docking and Molecular Dynamic Simulation

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