Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2020 Jan 17;25(2):395.
doi: 10.3390/molecules25020395.

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

Ahmad Omar Noor  1 , Diena Mohammedallam Almasri  1 , Alaa Abdullah Bagalagel  1 , Hossam Mohamed Abdallah  2   3 , Shaimaa Gamal Abdallah Mohamed  4 , Gamal Abdallah Mohamed  2   5 , Sabrin Ragab Mohamed Ibrahim  6   7
Affiliations
Review

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

Ahmad Omar Noor et al. Molecules. .

Abstract

Recently, the metabolites separated from endophytes have attracted significant attention, as many of them have a unique structure and appealing pharmacological and biological potentials. Isocoumarins represent one of the most interesting classes of metabolites, which are coumarins isomers with a reversed lactone moiety. They are produced by plants, microbes, marine organisms, bacteria, insects, liverworts, and fungi and possessed a wide array of bioactivities. This review gives an overview of isocoumarins derivatives from endophytic fungi and their source, isolation, structural characterization, biosynthesis, and bioactivities, concentrating on the period from 2000 to 2019. Overall, 307 metabolites and more than 120 references are conferred. This is the first review on these multi-facetted metabolites from endophytic fungi.

Keywords: biological activities; biosynthesis; dihydroisocoumarins; endophytes; isocoumarins.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Isocoumarin, 3,4-dihydroisocoumarin, coumarin, and isochroman skeletons.
Figure 2
Figure 2
Distribution of isocoumarin derivatives in different fungal genus.
Figure 3
Figure 3
Structures of isocoumarin derivatives 1–16.
Figure 4
Figure 4
Structures of isocoumarin derivatives 17–33.
Figure 5
Figure 5
Structures of isocoumarin derivatives 34–44.
Figure 6
Figure 6
Structures of isocoumarin derivatives 45–53.
Figure 7
Figure 7
Structures of isocoumarin derivatives 54–66.
Figure 8
Figure 8
Structures of isocoumarin derivatives 67–82.
Figure 9
Figure 9
Structures of isocoumarin derivatives 83–96.
Figure 10
Figure 10
Structures of isocoumarin derivatives 97–105.
Figure 11
Figure 11
Structures of isocoumarin derivatives 106–113.
Figure 12
Figure 12
Structures of isocoumarin derivatives 114–123.
Figure 13
Figure 13
Structures of isocoumarin derivatives 124–136.
Figure 14
Figure 14
Structures of isocoumarin derivatives 137–149.
Figure 15
Figure 15
Structure of isocoumarin derivatives 150–159.
Figure 16
Figure 16
Structures of isocoumarin derivatives 160–164.
Figure 17
Figure 17
Structures of isocoumarin derivatives 165–174.
Figure 18
Figure 18
Structures of isocoumarin derivatives 175–182.
Figure 19
Figure 19
Structures of isocoumarin derivatives 183–187.
Figure 20
Figure 20
Structures of isocoumarin derivatives 188–200.
Figure 21
Figure 21
Structures of isocoumarin derivatives 201–211.
Figure 22
Figure 22
Structures of isocoumarin derivatives 212–228.
Figure 23
Figure 23
Structures of isocoumarin derivatives 229–239.
Figure 24
Figure 24
Structures of isocoumarin derivatives 240–250.
Figure 25
Figure 25
Structures of isocoumarin derivatives 251–264.
Figure 26
Figure 26
Structures of isocoumarin derivatives 265–272.
Figure 27
Figure 27
Structures of isocoumarin derivatives 273–279.
Figure 28
Figure 28
Structures of isocoumarin derivatives 280–294.
Figure 29
Figure 29
Structures of isocoumarin derivatives 295–300.
Figure 30
Figure 30
Structures of isocoumarin derivatives 301–307.
Figure 31
Figure 31
Proposed biosynthetic pathway of 11, 35, 88, 90, and 165 [21,23,24,25,26].
Figure 32
Figure 32
Proposed biosynthetic pathway of 56 and 125 [27].
Figure 33
Figure 33
Proposed biosynthetic pathway of 273 [28].
Figure 34
Figure 34
Proposed biosynthetic pathway of 70, 71, 138, 179, and 180 [22].
Figure 35
Figure 35
Proposed biosynthetic pathway of 235, 236, and 296 [29].
See this image and copyright information in PMC

References

    1. Ibrahim S.R., Abdallah H.M., Mohamed G.A., Ross S.A. Integracides HJ: New tetracyclic triterpenoids from the endophytic fungus Fusarium sp. Fitoterapia. 2016;112:161–167. doi: 10.1016/j.fitote.2016.06.002. - DOI - PubMed
    1. Ibrahim S.R., Mohamed G.A., Khedr A.I. γ-Butyrolactones from Aspergillus species: Structures, biosynthesis, and biological activities. Nat. Prod. Commun. 2017;12:791–800. doi: 10.1177/1934578X1701200526. - DOI - PubMed
    1. Ibrahim S.R., Elkhayat E.S., Mohamed G.A., Khedr A.I., Fouad M.A., Kotb M.H., Ross S.A. Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus. Phytochem. Lett. 2015;14:84–90. doi: 10.1016/j.phytol.2015.09.006. - DOI
    1. Ibrahim S.R., Mohamed G.A., Moharram A.M., Youssef D.T. Aegyptolidines A and B: New pyrrolidine alkaloids from the fungus Aspergillus aegyptiacus. Phytochem. Lett. 2015;12:90–93. doi: 10.1016/j.phytol.2015.03.001. - DOI
    1. Ibrahim S.R., Mohamed G.A., Al Haidari R.A., El-Kholy A.A., Zayed M.F. Potential anti-malarial agents from endophytic fungi: A review. Mini Rev. Med. Chem. 2018;18:1110–1132. doi: 10.2174/1389557518666180305163151. - DOI - PubMed