Secondary Metabolites from the Endophytic Fungi F25 and Their Antifungal Activities

Overview

Journal Front Microbiol

Specialty Microbiology

Date 2023 Feb 23

PMID 36819056

Authors

Ziwei Song

Yan Jun Sun

Shuangyu Xu

Gang Li

Chunmao Yuan

Kang Zhou

Affiliations

Soon will be listed here.

Abstract

Seven new compounds, including three isocoumarins (-), three pyrrolidinone derivatives (-), and one pentaene diacid (), together with 13 known compounds, were isolated from the rice culture of the endophytic fungus F25. Their structures and stereochemistry were established using HRESIMS, NMR, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction. The possible biosynthetic pathways for compounds and - were proposed. The antifungal efficacies of compounds were evaluated against , and compounds , , and exhibited inhibitory activities against with MIC values of 256, 64 and 128 μg/mL, respectively.

Citing Articles

An Update of Fungal Endophyte Diversity and Strategies for Augmenting Therapeutic Potential of their Potent Metabolites: Recent Advancement.

Prajapati C, Rai S, Singh A, Chopade B, Singh Y, Singh S Appl Biochem Biotechnol. 2025; .

PMID: 39907846 DOI: 10.1007/s12010-024-05098-9.

Recent Updates on the Secondary Metabolites from Fungi and Their Biological Activities (Covering 2019 to 2024).

Amuzu P, Pan X, Hou X, Sun J, Jakada M, Odigie E J Fungi (Basel). 2024; 10(11).

PMID: 39590697 PMC: 11596042. DOI: 10.3390/jof10110778.

Simultaneous detection of multiple mycotoxins in Radix Dipsaci and estimation of exposure risk for consumers.

Wang L, Su D, Yuan Q, Xiao C, Hu M, Guo L Sci Rep. 2024; 14(1):22762.

PMID: 39354043 PMC: 11445475. DOI: 10.1038/s41598-024-73597-0.

The plant endomicrobiome: Structure and strategies to produce stress resilient future crop.

Vimal S, Singh J, Kumar A, Prasad S Curr Res Microb Sci. 2024; 6:100236.

PMID: 38756233 PMC: 11097330. DOI: 10.1016/j.crmicr.2024.100236.

GC-MS Based Characterization, Antibacterial, Antifungal and Anti-Oncogenic Activity of Ethyl Acetate Extract of Strain AK-6 Isolated from Rhizospheric Soil.

Niazi S, Basavarajappa D, Kumaraswamy S, Bepari A, Hiremath H, Nagaraja S Curr Issues Mol Biol. 2023; 45(5):3733-3756.

PMID: 37232710 PMC: 10217203. DOI: 10.3390/cimb45050241.

References

Wang H, Li G, Qiao Y, Sun Y, Peng X, Lou H . Chamiside A, a Cytochalasan with a Tricyclic Core Skeleton from the Endophytic Fungus Chaetomium nigricolor F5. Org Lett. 2019; 21(9):3319-3322. DOI: 10.1021/acs.orglett.9b01065. View

Hu Z, Xue Y, Bi X, Zhang J, Luo Z, Li X . Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii. Mar Drugs. 2014; 12(11):5563-75. PMC: 4245545. DOI: 10.3390/md12115563. View

Li G, Lou H . Strategies to diversify natural products for drug discovery. Med Res Rev. 2017; 38(4):1255-1294. DOI: 10.1002/med.21474. View

Zhang D, Tao X, Chen R, Liu J, Li L, Fang X . Pericoannosin A, a Polyketide Synthase-Nonribosomal Peptide Synthetase Hybrid Metabolite with New Carbon Skeleton from the Endophytic Fungus Periconia sp. Org Lett. 2015; 17(17):4304-7. DOI: 10.1021/acs.orglett.5b02123. View

Ola A, Thomy D, Lai D, Brotz-Oesterhelt H, Proksch P . Inducing secondary metabolite production by the endophytic fungus Fusarium tricinctum through coculture with Bacillus subtilis. J Nat Prod. 2013; 76(11):2094-9. DOI: 10.1021/np400589h. View

Shiono Y, Tsuchinari M, Shimanuki K, Miyajima T, Murayama T, Koseki T . Fusaristatins A and B, two new cyclic lipopeptides from an endophytic Fusarium sp. J Antibiot (Tokyo). 2007; 60(5):309-16. DOI: 10.1038/ja.2007.39. View

Liu X, Hou X, Song Y, Wang B, Ji N . Cyclonerane sesquiterpenes and an isocoumarin derivative from the marine-alga-endophytic fungus Trichoderma citrinoviride A-WH-20-3. Fitoterapia. 2020; 141:104469. DOI: 10.1016/j.fitote.2020.104469. View

Sheldrick G . SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr A Found Adv. 2014; 71(Pt 1):3-8. PMC: 4283466. DOI: 10.1107/S2053273314026370. View

Cui H, Liu Y, Nie Y, Liu Z, Chen S, Zhang Z . Polyketides from the Mangrove-Derived Endophytic Fungus Nectria sp. HN001 and Their α-Glucosidase Inhibitory Activity. Mar Drugs. 2016; 14(5). PMC: 4882560. DOI: 10.3390/md14050086. View

10.

Cao F, Yang J, Liu Y, Zhu H, Wang C . Pleosporalone A, the first azaphilone characterized with aromatic A-ring from a marine-derived Pleosporales sp. fungus. Nat Prod Res. 2016; 30(21):2448-52. DOI: 10.1080/14786419.2016.1198352. View

11.

Gao H, Li G, Lou H . Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes. Molecules. 2018; 23(3). PMC: 6017594. DOI: 10.3390/molecules23030646. View

12.

Zhang H, Song Y, Tan R . Biology and chemistry of endophytes. Nat Prod Rep. 2006; 23(5):753-71. DOI: 10.1039/b609472b. View

13.

Hirota A, Nemoto A, Tsuchiya Y, Hojo H, Abe N . Isolation of a 2-Pyrone Compound as an Antioxidant from a Fungus and Its New Reaction Product with 1,1-Diphenyl-2-picrylhydrazyl Radical. Biosci Biotechnol Biochem. 2016; 63(2):418-20. DOI: 10.1271/bbb.63.418. View

14.

Gupta S, Chaturvedi P, Kulkarni M, van Staden J . A critical review on exploiting the pharmaceutical potential of plant endophytic fungi. Biotechnol Adv. 2019; 39:107462. DOI: 10.1016/j.biotechadv.2019.107462. View

15.

Tian C, Gao H, Peng X, Li G, Lou H . Fusidic acid derivatives from the endophytic fungus F47. J Asian Nat Prod Res. 2021; 23(12):1148-1155. DOI: 10.1080/10286020.2020.1866559. View

16.

Li J, Liu S, Niu S, Zhuang W, Che Y . Pyrrolidinones from the ascomycete fungus Albonectria rigidiuscula. J Nat Prod. 2009; 72(12):2184-7. DOI: 10.1021/np900619z. View

17.

Li G, Kusari S, Kusari P, Kayser O, Spiteller M . Endophytic Diaporthe sp. LG23 Produces a Potent Antibacterial Tetracyclic Triterpenoid. J Nat Prod. 2015; 78(8):2128-32. DOI: 10.1021/acs.jnatprod.5b00170. View

18.

Jiang J, Li F, Feng Z, Yang Y, Zhang P . New phenolic glycosides from . J Asian Nat Prod Res. 2019; 22(1):17-23. DOI: 10.1080/10286020.2019.1646730. View

19.

Guo H, Wu Q, Chen D, Jiang M, Chen B, Lu Y . Absolute configuration of polypropionate derivatives: Decempyrones A-J and their MptpA inhibition and anti-inflammatory activities. Bioorg Chem. 2021; 115:105156. DOI: 10.1016/j.bioorg.2021.105156. View