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
. 2022 Apr 6;20(4):255.
doi: 10.3390/md20040255.

New 3-Acyl Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus Lecanicillium fusisporum

Xinya Xu  1 , Yanhui Tan  2 , Chenghai Gao  1 , Kai Liu  1 , Zhenzhou Tang  1 , Chunju Lu  1 , Haiyan Li  1 , Xiaoyong Zhang  3 , Yonghong Liu  1
Affiliations

New 3-Acyl Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus Lecanicillium fusisporum

Xinya Xu et al. Mar Drugs. .

Abstract

Seven rare C3-C6 reduced 3-acyl tetramic acid derivatives, lecanicilliumins A-G (1-7), along with the known analogue cladosporiumin D (8), were obtained from the extract of the deep-sea-derived fungus Lecanicillium fusisporum GXIMD00542 within the family Clavipitacae. Their structures were elucidated by extensive spectroscopic data analysis, quantum chemistry calculations and chemical reaction. Compounds 1, 2, 5-7 exhibited moderate anti-inflammatory activity against NF-κB production using lipopolysaccharide (LPS) induced RAW264.7 cells with EC50 values range of 18.49-30.19 μM.

Keywords: Lecanicillium fusisporum; anti-inflammatory activity; clavipitacae; deep-sea fungus; tetramic acid derivatives.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The interconverting internal tautomers of 3-acyl tetramic acid [5].
Figure 2
Figure 2
The chemical structures of compounds 1–8.
Figure 3
Figure 3
(A) Key 1H-1H COSY and HMBC correlations for compounds 1–7. (B) Key NOESY correlations for compounds 1–7. (C) The Δδ (δS−δR) values for MTPA esters of 7.
Figure 4
Figure 4
X-ray ORTEP drawing of compound 1. The crystal structure was deposited at the Cambridge Crystallographic Data Centre with number of CCDC 2092073.
Figure 5
Figure 5
Comparison of calculated ECD spectra of (3S,6S,10R)-2a (red), (3S,6R,10S)-2b (gray) in MeOH and experimental CD (black). σ = 0.3 eV, UV shift = 7 nm.
Figure 6
Figure 6
Comparison of calculated ECD spectra of (3S,6S,9S)-4a (red), (3S,6R,9R)-4b (gray), (3R,6R,9R)-4c (dashed gray) and (3R,6S,9S)-4d (dashed orange) and experimental CD (black). σ = 0.3 eV; UV shift = 7 nm.
See this image and copyright information in PMC

References

    1. Pang X., Chen W., Wang X., Zhou X., Yang B., Tian X., Wang J., Xu S., Liu Y. New tetramic acid derivatives from the deep-sea-derived fungus Penicillium sp. SCSIO06868 with SARS-CoV-2 M(pro) inhibitory activity evaluation. Front. Microbiol. 2021;12:730807. doi: 10.3389/fmicb.2021.730807. - DOI - PMC - PubMed
    1. Mo X., Gulder T. Biosynthetic strategies for tetramic acid formation. Nat. Prod. Rep. 2021;38:1555–1566. doi: 10.1039/D0NP00099J. - DOI - PubMed
    1. Ghisalberti E.L. Bioactive Tetramic Acid Metabolites. In: Rahman A., editor. Studies in Natural Products Chemistry. Vol. 28. Elsevier; Amsterdam, The Netherlands: 2003. pp. 109–163. - DOI
    1. Jiang M., Chen S., Li J., Liu L. The biological and chemical diversity of tetramic acid compounds from marine-derived microorganisms. Mar. Drugs. 2020;18:114. doi: 10.3390/md18020114. - DOI - PMC - PubMed
    1. Royles B.J.L. Naturally Occurring Tetramic Acids: Structure, Isolation, and Synthesis. Chem. Rev. 1995;95:1981–2001. doi: 10.1021/cr00038a009. - DOI

Supplementary concepts

LinkOut - more resources