Phenyl Ethers from the Marine-Derived Fungus and Their Antimicrobial Activity Against Plant Pathogenic Fungi and Bacteria

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Sep 26

PMID 36157764

Authors

Minh Van Nguyen

Jae Woo Han

Hun Kim

Gyung Ja Choi

Affiliations

Soon will be listed here.

Abstract

Marine fungi produce various secondary metabolites with unique chemical structures and diverse biological activities. In the continuing search for new antifungal agents from fungi isolated from marine environments, the culture filtrate of a fungus SFC20160407-M11 exhibited the potential to control plant diseases caused by fungi. From the culture filtrate of SFC20160407-M11, a total of seven compounds were isolated and identified by activity-guided column chromatography and spectroscopic analysis: violaceol I (), violaceol II (), diorcinol (), versinol (), orcinol (), orsellinic acid (), and sydowiol C (). Based on bioassays against 17 plant pathogenic fungi and bacteria, violaceols and diorcinol (-) showed a broad spectrum of antimicrobial activity with minimum inhibitory concentration values in the range of 6.3-200 μg mL. These compounds also effectively reduced the development of rice blast, tomato late blight, and pepper anthracnose caused by plant pathogenic fungi in a dose-dependent manner. Our results suggest that SFC20160407-M11 and its phenyl ether compounds could be used for developing new antimicrobial agents to protect crops from plant pathogens.

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References

Takenaka Y, Tanahashi T, Nagakura N, Hamada N . Phenyl ethers from cultured lichen mycobionts of Graphis scripta var. serpentina and G. rikuzensis. Chem Pharm Bull (Tokyo). 2003; 51(7):794-7. DOI: 10.1248/cpb.51.794. View

Ngo M, Nguyen M, Han J, Kim B, Kim Y, Park M . Biocontrol Potential of Species Producing Antimicrobial Metabolites. Front Microbiol. 2022; 12:804333. PMC: 8733401. DOI: 10.3389/fmicb.2021.804333. View

Lopes T, Coelho R, Yoshida N, Honda N . Radical-scavenging activity of orsellinates. Chem Pharm Bull (Tokyo). 2008; 56(11):1551-4. DOI: 10.1248/cpb.56.1551. View

Dong J, Huang S, Hao Y, Wang Z, Liu Y, Li Y . Marine-natural-products for biocides development: first discovery of meridianin alkaloids as antiviral and anti-phytopathogenic-fungus agents. Pest Manag Sci. 2019; 76(10):3369-3376. DOI: 10.1002/ps.5690. View

Wang Y, Mou Y, Dong Y, Wu Y, Liu B, Bai J . Diphenyl Ethers from a Marine-Derived . Mar Drugs. 2018; 16(11). PMC: 6267227. DOI: 10.3390/md16110451. View

El-Hawary S, Moawad A, Bahr H, Abdelmohsen U, Mohammed R . Natural product diversity from the endophytic fungi of the genus . RSC Adv. 2022; 10(37):22058-22079. PMC: 9054607. DOI: 10.1039/d0ra04290k. View

Fremlin L, Piggott A, Lacey E, Capon R . Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor. J Nat Prod. 2009; 72(4):666-70. DOI: 10.1021/np800777f. View

Zhang M, Ding X, Kang J, Gao Y, Wang Z, Wang Q . Marine Natural Product for Pesticide Candidate: Pulmonarin Alkaloids as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents. J Agric Food Chem. 2020; 68(41):11350-11357. DOI: 10.1021/acs.jafc.0c04868. View

Saetang P, Rukachaisirikul V, Phongpaichit S, Preedanon S, Sakayaroj J, Hadsadee S . Antibacterial and Antifungal Polyketides from the Fungus PSU-MF16. J Nat Prod. 2021; 84(5):1498-1506. DOI: 10.1021/acs.jnatprod.0c01308. View

10.

Liu F, Chen G, Zhang L, Liu B, Chen S, Hua H . Isolation and structure elucidation of a new compound from the fungus Aspergillus flavipes PJ03-11. Nat Prod Res. 2017; 32(1):30-35. DOI: 10.1080/14786419.2017.1326490. View

11.

Song Q, Nan Z, Gao K, Song H, Tian P, Zhang X . Antifungal, Phytotoxic, and Cytotoxic Activities of Metabolites from Epichloë bromicola, a Fungus Obtained from Elymus tangutorum Grass. J Agric Food Chem. 2015; 63(40):8787-92. DOI: 10.1021/acs.jafc.5b04260. View

12.

Romsdahl J, Wang C . Recent advances in the genome mining of secondary metabolites (covering 2012-2018). Medchemcomm. 2019; 10(6):840-866. PMC: 6590338. DOI: 10.1039/c9md00054b. View

13.

Peng J, Shen X, El Sayed K, Dunbar D, Perry T, Wilkins S . Marine natural products as prototype agrochemical agents. J Agric Food Chem. 2003; 51(8):2246-52. PMC: 4969014. DOI: 10.1021/jf0207880. View

14.

Vu T, Kim H, Tran V, Vu H, Hoang T, Han J . Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt. PLoS One. 2017; 12(7):e0181499. PMC: 5526539. DOI: 10.1371/journal.pone.0181499. View

15.

Ingavat N, Mahidol C, Ruchirawat S, Kittakoop P . Asperaculin A, a sesquiterpenoid from a marine-derived fungus, Aspergillus aculeatus. J Nat Prod. 2011; 74(7):1650-2. DOI: 10.1021/np200221w. View

16.

Lee S, Park M, Lim Y . Diversity of Marine-Derived from Tidal Mudflats and Sea Sand in Korea. Mycobiology. 2017; 44(4):237-247. PMC: 5287156. DOI: 10.5941/MYCO.2016.44.4.237. View

17.

Srivastava V, Darokar M, Fatima A, Kumar J, Chowdhury C, Saxena H . Synthesis of diverse analogues of Oenostacin and their antibacterial activities. Bioorg Med Chem. 2006; 15(1):518-25. DOI: 10.1016/j.bmc.2006.09.034. View

18.

Huang Z, Nong X, Ren Z, Wang J, Zhang X, Qi S . Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502. Bioorg Med Chem Lett. 2017; 27(4):787-791. DOI: 10.1016/j.bmcl.2017.01.032. View

19.

Li Z, Wang X, Ren G, Yuan X, Deng N, Ji G . Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus . Molecules. 2018; 23(9). PMC: 6225247. DOI: 10.3390/molecules23092368. View

20.

Kim B, Han J, Ngo M, Le Dang Q, Kim J, Kim H . Identification of novel compounds, oleanane- and ursane-type triterpene glycosides, from Trevesia palmata: their biocontrol activity against phytopathogenic fungi. Sci Rep. 2018; 8(1):14522. PMC: 6162204. DOI: 10.1038/s41598-018-32956-4. View