Antibacterial Naphthalene Derivatives from the Fermentation Products of the Endophytic Fungus Phomopsis fukushii

Li, Xuemei; Mi, Qi-Li; Gao, Qian; Li, Jing; Song, Chunman; Zeng, Wan-Li; Xiang, Hai-Ying; Liu, Xin; Chen, Jianhua; Zhang, Chengming; Yang, Guangyu; Hu, Qiu‐Fen; Chen, Zhangyu

doi:10.1007/s10600-021-03340-y

Cited by 5 publications

(4 citation statements)

References 17 publications

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“…Furthermore, naphthalene derivatives from the endophytic fungus Phomopsis fukushii inhibited the growth of S. aureus (Li et al. 2021 ). A synthetic naphthalene compound, ( E )-3-(2,3,4-trimethoxyphenyl)-1-(naphth-2-yl)-prop-2-en-1-one, inhibited the growth of four cancer cell lines: PC-3 human prostate cancer cell line, OVCAR human ovarian cancer cell line, IMR-32 human neuroblastoma cell line, and HEP-2 human hepatocellular liver carcinoma cell line (Budhiraja et al.…”

Section: Discussionmentioning

confidence: 99%

Thais savignyi tissue extract: bioactivity, chemical composition, and molecular docking

Habib

Hamed²,

Ali

et al. 2022

Pharmaceutical Biology

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Context Thais savignyi Deshayes (Muricidae) is widely distributed in the Red Sea. Its abundance and the history of Muricidae in traditional medicine make it a tempting target for investigation. Objective To investigate the chemical profile and biological activities of T. savignyi tissue extracts. Materials and methods Methanol, ethanol, acetone, and ethyl acetate extracts from T. savignyi tissue were compared in their antioxidant by total antioxidant capacity, DPPH free radical scavenging, and total phenolic content. In addition, the antimicrobial, and antibiofilm properties (at 250 µg/mL) of the extracts were tested against Escherichia coli , Pseudomonas aeruginosa , Proteus vulgaris , Klebsiella pneumoniae , Staphylococcus aureus , and Candida albicans . The antioxidant extract with greatest activity was assessed for cytotoxicity (range 0.4–100 µg/mL) against 3 human cancer cell lines (UO-31, A549 and A431), and its chemical composition was investigated using GC-MS. Moreover, docking simulation was performed to predict its constituents’ binding modes/scores to the active sites of thymidylate kinase. Results The ethyl acetate extract ( Ts -EtOAc) showed the highest total antioxidant capacity (551.33 mg AAE/g dry weight), total phenolics (254.46 mg GAE/g dry weight), and DPPH scavenging (IC 50 = 24.0 µg/mL). Ts -EtOAc exhibited strong antibacterial (MIC: 3.9 µg/mL against K. pneumoniae ), antibiofilm (MIC: 7.81 µg/mL against S. aureus ), and antifungal (MIC: 3.9 µg/mL against C. albicans ) activities and considerable cytotoxicity against cancer cells (UO-31: IC 50 = 19.96 ± 0.93, A549: IC 50 = 25.04 ± 1.15 μg/mL). GC-MS identified multiple bioactive metabolites in Ts -EtOAc extract belonging to miscellaneous chemical classes. Molecular docking studies revealed that the constituents of Ts -EtOAc have antibacterial potential. Discussion and conclusions T. savignyi extract has considerable antimicrobial and cytotoxic activities. Further studies are needed to isolate the active constituents of this snail for comprehensive drug discovery tests.

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Section: Discussionmentioning

confidence: 99%

Thais savignyi tissue extract: bioactivity, chemical composition, and molecular docking

Habib

Hamed²,

Ali

et al. 2022

Pharmaceutical Biology

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“…Two novel naphthalene derivatives, 1-(3-hydroxy-1-(hydroxymethyl)-2-methoxy-6methylnaphthalen-7-yl) propan-2-one (4) and 1-(3-hydroxy-1-(hydroxymethyl)-6-methylnaphthalen-7-yl)propan-2-one (5, Figure 1), were obtained from the Phomopsis fukushii. Compounds 4 and 5 displayed poor anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity, with zones of inhibition of 10.2 and 11.3 mm, respectively (6 mm sterile filter paper discs were impregnated with 20 µL (50 µg) of each compound) [20]. Earlier Phomopsis fukushii (Diaporthe fukushii) isolated from the rhizome of Paris polyphylla var.…”

Section: Diaporthe (Asexual State: Phomopsis)mentioning

confidence: 99%

“…lachrymans with MIC values of 15.6 µg/mL, and compounds (−)-1 (20 and 21) displayed poor activity with MICs of 31.2 µg/mL each. Compounds (−)-1, (+)-1, (20,21,22) showed antibacterial activity against Xanthomonas citri pv. phaseoli var.…”

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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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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“…Two new compounds, 1-(3-hydroxy-1-(hydroxymethyl)-2-methoxy-6-methylnaphthalen-7-yl) propan-2-one ( 147 ) and 1-(3-hydroxy-1-(hydroxymethyl)-6-methylnaphthalen-7-yl)propan-2-one ( 148 ), have been isolated from the endophytic fungus Phomopsis fukushii obtained from N. tabacum. These compounds show weak activities against methicillin-resistant S. aureus , with the diameter of the inhibition zone being 10–11 mm [ 138 ].…”

Section: Effects Of Natural Compounds Obtained From Endophytes On Ant...mentioning

confidence: 99%

Antimicrobial Action Mechanisms of Natural Compounds Isolated from Endophytic Microorganisms

Eshboev,

Mamadalieva,

Nazarov

et al. 2024

Antibiotics

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Infectious diseases are a significant challenge to global healthcare, especially in the face of increasing antibiotic resistance. This urgent issue requires the continuous exploration and development of new antimicrobial drugs. In this regard, the secondary metabolites derived from endophytic microorganisms stand out as promising sources for finding antimicrobials. Endophytic microorganisms, residing within the internal tissues of plants, have demonstrated the capacity to produce diverse bioactive compounds with substantial pharmacological potential. Therefore, numerous new antimicrobial compounds have been isolated from endophytes, particularly from endophytic fungi and actinomycetes. However, only a limited number of these compounds have been subjected to comprehensive studies regarding their mechanisms of action against bacterial cells. Furthermore, the investigation of their effects on antibiotic-resistant bacteria and the identification of biosynthetic gene clusters responsible for synthesizing these secondary metabolites have been conducted for only a subset of these promising compounds. Through a comprehensive analysis of current research findings, this review describes the mechanisms of action of antimicrobial drugs and secondary metabolites isolated from endophytes, antibacterial activities of the natural compounds derived from endophytes against antibiotic-resistant bacteria, and biosynthetic gene clusters of endophytic fungi responsible for the synthesis of bioactive secondary metabolites.

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Antibacterial Naphthalene Derivatives from the Fermentation Products of the Endophytic Fungus Phomopsis fukushii

Cited by 5 publications

References 17 publications

Thais savignyi tissue extract: bioactivity, chemical composition, and molecular docking

Thais savignyi tissue extract: bioactivity, chemical composition, and molecular docking

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Antimicrobial Action Mechanisms of Natural Compounds Isolated from Endophytic Microorganisms

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