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
. 2021 Jan 12;19(1):32.
doi: 10.3390/md19010032.

New Deoxyisoaustamide Derivatives from the Coral-Derived Fungus Penicillium dimorphosporum KMM 4689

Olesya I Zhuravleva  1   2 , Alexandr S Antonov  1 , Vo Thi Dieu Trang  3 , Mikhail V Pivkin  1 , Yuliya V Khudyakova  1 , Vladimir A Denisenko  1 , Roman S Popov  1 , Natalya Y Kim  1 , Ekaterina A Yurchenko  1 , Andrey V Gerasimenko  4 , Anatoly A Udovenko  4 , Gunhild von Amsberg  5   6 , Sergey A Dyshlovoy  1   2   5   6 , Shamil S Afiyatullov  1
Affiliations

New Deoxyisoaustamide Derivatives from the Coral-Derived Fungus Penicillium dimorphosporum KMM 4689

Olesya I Zhuravleva et al. Mar Drugs. .

Abstract

Seven new deoxyisoaustamide derivatives (1-7) together with known compounds (8-10) were isolated from the coral-derived fungus Penicillium dimorphosporum KMM 4689. Their structures were established using spectroscopic methods, X-ray diffraction analysis and by comparison with related known compounds. The absolute configurations of some alkaloids were determined based on CD and NOESY data as well as biogenetic considerations. The cytotoxic and neuroprotective activities of some of the isolated compounds were examined and structure-activity relationships were pointed out. New deoxyisoaustamides 4-6 at concentration of 1 µM revealed a statistical increase of PQ(paraquat)-treated Neuro-2a cell viability by 30-39%.

Keywords: Penicillium dimorphosporum; deoxyisoaustamide; neuroprotective activity; paraquat; prenylated indole diketopiperazines; secondary metabolites.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of 1–10.
Figure 2
Figure 2
X-ray crystallographic structure of compound 1.
Figure 3
Figure 3
Key COSY and HMBC correlations of 2 and 3.
Figure 4
Figure 4
(a) CD spectra of 2(blue) and 5(red); (b) CD spectra of 3(blue) and 6(red).
Figure 5
Figure 5
Effects of compounds 1–10 on viability of PQ (paraquat)-treated Neuro-2a cells. Each bar represents the mean ± SEM of three independent replicates. (*) indicate p < 0.05 versus PQ-treated cells. The difference between control and PQ-treated cells was significant (p < 0.05).
See this image and copyright information in PMC

References

    1. Ma Y.-M., Liang X.-A., Kong Y., Jia B. Structural diversity and biological activities of indole diketopiperazine alkaloids from fungi. J. Agric. Food Chem. 2016;64:6659–6671. doi: 10.1021/acs.jafc.6b01772. - DOI - PubMed
    1. Steyn P.S. The structures of five diketopiperazines from Aspergillus ustus. Tetrahedron. 1973;29:107–120. doi: 10.1016/S0040-4020(01)99384-6. - DOI
    1. Quang T.H., Lee D.-S., Sohn J.H., Kim Y.-C., Oh H. A new deoxyisoaustamide derivative from the marine-derived fungus Penicillium sp. JF-72. Bull. Korean Chem. Soc. 2013;34:3109–3112. doi: 10.5012/bkcs.2013.34.10.3109. - DOI
    1. Zhuravleva O.I., Afiyatullov S.S., Denisenko V.A., Ermakova S.P., Slinkina N.N., Dmitrenok P.S., Kim N.Y. Secondary Metabolites from a Marine-Derived Fungus Aspergillus carneus Blochwitz. Phytochemistry. 2012;80:123–131. doi: 10.1016/j.phytochem.2012.05.008. - DOI - PubMed
    1. Peng J., Gao H., Li J., Ai J., Geng M., Zhang G., Zhu T., Gu Q., Li D. Prenylated indole diketopiperazines from the marine-derived fungus Aspergillus versicolor. J. Org. Chem. 2014;79:7895–7904. doi: 10.1021/jo5010179. - DOI - PubMed

MeSH terms

Supplementary concepts

LinkOut - more resources