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
Comparative Study
. 2020 Oct 30;18(11):547.
doi: 10.3390/md18110547.

Lipopeptide Epimers and a Phthalide Glycerol Ether with AChE Inhibitory Activities from the Marine-Derived Fungus Cochliobolus Lunatus SCSIO41401

Yu Dai  1 , Kunlong Li  1   2 , Jianglian She  1 , Yanbo Zeng  3 , Hao Wang  3 , Shengrong Liao  1   2 , Xiuping Lin  1   2 , Bin Yang  1   2 , Junfeng Wang  1   2 , Huaming Tao  4 , Haofu Dai  3 , Xuefeng Zhou  1   2 , Yonghong Liu  1   2   5
Affiliations
Comparative Study

Lipopeptide Epimers and a Phthalide Glycerol Ether with AChE Inhibitory Activities from the Marine-Derived Fungus Cochliobolus Lunatus SCSIO41401

Yu Dai et al. Mar Drugs. .

Abstract

A pair of novel lipopeptide epimers, sinulariapeptides A (1) and B (2), and a new phthalide glycerol ether (3) were isolated from the marine algal-associated fungus Cochliobolus lunatus SCSIO41401, together with three known chromanone derivates (4-6). The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD), and Mo2 (OAc)4-induced ECD methods. The new compounds 1-3 showed moderate inhibitory activity against acetylcholinesterase (AChE), with IC50 values of 1.3-2.5 μM, and an in silico molecular docking study was also performed.

Keywords: AChE inhibitory; Cochliobolus lunatus; absolute configurations; lipopeptides; phthalide.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
Compounds 1–6, isolated from fungal strain SCSIO41401.
Figure 2
Figure 2
The key HMBC, COSY, and ROESY correlations of 1–3.
Figure 3
Figure 3
(A) Experimental CD spectra of 1, and the calculated ECD spectra of its truncated models. (B) Experimental CD spectra of 2, and the calculated ECD spectra of its truncated models. (C) Experimental CD spectra of 3 in MeOH. (D) Induced CD (ICD) spectra from the Mo2-complexes of 3 in DMSO.
Figure 4
Figure 4
Molecular docking of 1–3 with AChE (PDB code: 4EY7). The binding sites of the molecules 1 (A1), 2 (A2) and 3 (A3) with the AChE protein. The 2D interaction details of the predicted binding mode of 1 (B1), 2 (B2) and 3 (B3) with the AChE.
See this image and copyright information in PMC

References

    1. Puglisi M.P., Sneed J.M., Ritson-Williams R., Young R. Marine chemical ecology in benthic environments. Nat. Prod. Rep. 2019;36:410–429. doi: 10.1039/C8NP00061A. - DOI - PubMed
    1. Moodie L.W.K., Sepčić K., Turk T., Frangež R., Svenson J. Natural cholinesterase inhibitors from marine organisms. Nat. Prod. Rep. 2019;36:1053–1092. doi: 10.1039/C9NP00010K. - DOI - PubMed
    1. Zagorska A., Jaromin A. Perspectives for New and More Efficient Multifunctional Ligands for Alzheimer’s Disease Therapy. Molecules. 2020;25:3337. doi: 10.3390/molecules25153337. - DOI - PMC - PubMed
    1. Prasasty V., Radifar M., Istyastono E. Natural Peptides in Drug Discovery Targeting Acetylcholinesterase. Molecules. 2018;23:2344. doi: 10.3390/molecules23092344. - DOI - PMC - PubMed
    1. Fang W., Wang J., Wang J., Shi L., Li K., Lin X., Min Y., Yang B., Tang L., Liu Y., et al. Cytotoxic and Antibacterial Eremophilane Sesquiterpenes from the Marine-Derived Fungus Cochliobolus lunatus SCSI041401. J. Nat. Prod. 2018;81:1405–1410. doi: 10.1021/acs.jnatprod.8b00015. - DOI - PubMed

Publication types

MeSH terms

Supplementary concepts

LinkOut - more resources