Two New Diphenyl Ether Derivatives from the Fermentation Products of the Endophytic Fungus Phomopsis asparagi

Hu, Shanshan; Liang, Meng-Jie; Mi, Qi-Li; Chen, Wei; Ling, Jun; Chen, Xing; Li, Jing; Yang, Guangyu; Hu, Qiu‐Fen; Wang, Weiguang; Guo, Yanbin

doi:10.1007/s10600-019-02828-y

Cited by 9 publications

(17 citation statements)

References 15 publications

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“…yunnanensis was the source of two new di-Ph ethers, 4-(3-methoxy-5-methylphenoxy)-2-(2hydroxyethyl)-6-(hydroxymethyl)phenol (25), and 4-(3-hydroxy-5-methylphenoxy)-2-(2hydroxyethyl)-6-(hydroxymethyl)phenol (26, Figure 2). Compounds 25 and 26 exhibited potent anti-MRSA activity with 10.8 and 11.4 mm inhibition zones, respectively [29].…”

Section: Diaporthe (Asexual State: Phomopsis)mentioning

confidence: 99%

“…The endophytic fungus Diaporthe terebinthifolii LGMF907 associated with the plant Schinus terebinthifolius yielded diaporthin (29) and orthosporin (30, Figure 2). Compound 29 displayed antimicrobial activity against various pathogens like E. coli, Micrococcus luteus, MRSA, and S. aureus with 1.73, 2.47, 9.50, and 9.0 mm zones of inhibition, respectively at 100 µg/disk concentration.…”

Section: Diaporthe (Asexual State: Phomopsis)mentioning

confidence: 99%

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Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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Antibiotic resistance is becoming a burning issue due to the frequent use of antibiotics for curing common bacterial infections, indicating that we are running out of effective antibiotics. This has been more obvious during recent corona pandemics. Similarly, enhancement of antimicrobial resistance (AMR) is strengthening the pathogenicity and virulence of infectious microbes. Endophytes have shown expression of various new many bioactive compounds with significant biological activities. Specifically, in endophytic fungi, bioactive metabolites with unique skeletons have been identified which could be helpful in the prevention of increasing antimicrobial resistance. The major classes of metabolites reported include anthraquinone, sesquiterpenoid, chromone, xanthone, phenols, quinones, quinolone, piperazine, coumarins and cyclic peptides. In the present review, we reported 451 bioactive metabolites isolated from various groups of endophytic fungi from January 2015 to April 2021 along with their antibacterial profiling, chemical structures and mode of action. In addition, we also discussed various methods including epigenetic modifications, co-culture, and OSMAC to induce silent gene clusters for the production of noble bioactive compounds in endophytic fungi.

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Section: Diaporthe (Asexual State: Phomopsis)mentioning

confidence: 99%

Section: Diaporthe (Asexual State: Phomopsis)mentioning

confidence: 99%

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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“…yunnanensis , collected in Kunming, Yunnan, China. These compounds displayed anti-methicillin-resistant S. aureus (anti-MRSA) activities with inhibition zone diameters (IZD) 10.8 ± 2.0 and 11.4 ± 1.8 mm, respectively [ 64 ]. Three new diphenyl ethers, 4-(3-methoxy-5-methylphenoxy)-2-(2-hydroxyethyl)-6-methylphenol ( 120 ), 4-(3-hydroxy-5-methylphenoxy)-2-(2-hydroxyethyl)-6-methylphenol ( 121 ), and 4-(3-methoxy-5-methylphenoxy)-2-(3-hydroxypropyl)-6-methylphenol ( 122 ), were extracted from P .…”

Section: Bioactive Secondary Metabolites From Phomopsis mentioning

confidence: 99%

Bioactive Secondary Metabolites of the Genus Diaporthe and Anamorph Phomopsis from Terrestrial and Marine Habitats and Endophytes: 2010–2019

Wang

et al. 2021

Microorganisms

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The genus Diaporthe and its anamorph Phomopsis are distributed worldwide in many ecosystems. They are regarded as potential sources for producing diverse bioactive metabolites. Most species are attributed to plant pathogens, non-pathogenic endophytes, or saprobes in terrestrial host plants. They colonize in the early parasitic tissue of plants, provide a variety of nutrients in the cycle of parasitism and saprophytism, and participate in the basic metabolic process of plants. In the past ten years, many studies have been focused on the discovery of new species and biological secondary metabolites from this genus. In this review, we summarize a total of 335 bioactive secondary metabolites isolated from 26 known species and various unidentified species of Diaporthe and Phomopsis during 2010–2019. Overall, there are 106 bioactive compounds derived from Diaporthe and 246 from Phomopsis, while 17 compounds are found in both of them. They are classified into polyketides, terpenoids, steroids, macrolides, ten-membered lactones, alkaloids, flavonoids, and fatty acids. Polyketides constitute the main chemical population, accounting for 64%. Meanwhile, their bioactivities mainly involve cytotoxic, antifungal, antibacterial, antiviral, antioxidant, anti-inflammatory, anti-algae, phytotoxic, and enzyme inhibitory activities. Diaporthe and Phomopsis exhibit their potent talents in the discovery of small molecules for drug candidates.

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“…Diphenyl ethers have been reported to possess significant antibacterial activity, especially against Gram-positive bacteria, − and structure–activity relationship analysis showed that prenylation might play an important role to increase antibacterial activity of the compounds. The isopentenyl flavonoids displayed antibacterial activity against Gram-positive pathogens with multidrug-resistance, which may be due to compounds interacting with the phospholipids of the bacterial membrane, dissipating the proton motive force, and degrading membrane permeability .…”

Section: Resultsmentioning

confidence: 99%

“…From this ecological aspect, endophytic fungi are an important source of antibacterial substances, especially as a source of compounds active against MDR bacteria . In recent years, more and more diphenyl ether derivatives have been isolated from plant endophytic fungi and have attracted special attention due to their excellent antibacterial activity. − …”

mentioning

confidence: 99%

Diphenyl Ether Derivative Rhexocerins and Rhexocercosporins from the Endophytic Fungus Rhexocercosporidium sp. Dzf14 Active against Gram-Positive Bacteria with Multidrug-Resistance

Gong

et al. 2023

J. Nat. Prod.

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Ten new diphenyl ether polyketides, including rhexocerins A−D (1−4) and rhexocercosporins A−F (5−10), together with three known congeners (11−13), were isolated from the endophytic fungus Rhexocercosporidium sp. Dzf14 obtained from Dioscorea zingiberensis. Their structures were elucidated by analysis of NMR and HRESIMS data, and their absolute configurations were determined by quantum chemical ECD calculations and X-ray crystallography. Compounds 1−4 featured an unprecedented tetracyclic carbon skeleton (6/7/5/6). Among them, compounds 1 and 5−9 showed antibacterial activities against methicillin-resistant S. aureus T144 and vancomycin-resistant E. faecalis 10.

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Two New Diphenyl Ether Derivatives from the Fermentation Products of the Endophytic Fungus Phomopsis asparagi

Cited by 9 publications

References 15 publications

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Bioactive Secondary Metabolites of the Genus Diaporthe and Anamorph Phomopsis from Terrestrial and Marine Habitats and Endophytes: 2010–2019

Diphenyl Ether Derivative Rhexocerins and Rhexocercosporins from the Endophytic Fungus Rhexocercosporidium sp. Dzf14 Active against Gram-Positive Bacteria with Multidrug-Resistance

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