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. 2017 Feb 17;15(2):43.
doi: 10.3390/md15020043.

Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025

Affiliations

Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025

Xinya Xu et al. Mar Drugs. .

Abstract

Four new compounds (1-4), including two brevianamides and two mycochromenic acid derivatives along with six known compounds were isolated from the deep-sea-derived fungus Penicillium brevicompactum DFFSCS025. Their structures were elucidated by spectroscopic analysis. Moreover, the absolute configurations of 1 and 2 were determined by quantum chemical calculations of the electronic circular dichroism (ECD) spectra. Compound 9 showed moderate cytotoxicity against human colon cancer HCT116 cell line with IC50 value of 15.6 μM. In addition, 3 and 5 had significant antifouling activity against Bugula neritina larval settlement with EC50 values of 13.7 and 22.6 μM, respectively. The NMR data of 6, 8, and 9 were assigned for the first time.

Keywords: Brevianamide; Mycochromenic acid derivative; Penicillium brevicompactum; antifouling; cytotoxicity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of Compounds 110.
Figure 2
Figure 2
Key HMBC and COSY correlations of 14.
Figure 3
Figure 3
Key NOESY correlations (dashed arrows) of 1 (left) and 2 (right).
Figure 4
Figure 4
Comparison of the measured and calculated ECD spectra of 1 (a) and 2 (b). (a) ECD spectra of (3S, 11R, 17R, 19R)-1 in MeOH (σ = 0.3 eV, shift = −3 nm); (b) ECD spectra of (3S, 11S, 17S, 19R)-2 in MeOH (σ = 0.27 eV, shift = −2 nm).
Figure 5
Figure 5
Comparison of the measured ECD spectrum of 4 with B3LYP/TZVP calculated spectra of (S)- and (R)-4 in MeOH (σ = 0.20 eV, shift = −18 nm).

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References

    1. Skropeta D. Deep-sea natural products. Nat. Prod. Rep. 2008;25:1131–1166. doi: 10.1039/b808743a. - DOI - PubMed
    1. Skropeta D., Wei L. Recent advances in deep-sea natural products. Nat. Prod. Rep. 2014;31:999–1025. doi: 10.1039/C3NP70118B. - DOI - PubMed
    1. Zhang W., Liu Z., Li S., Yang T., Zhang Q., Ma L., Tian X., Zhang H., Huang C., Zhang S., et al. Spiroindimicins A–D: New bisindole alkaloids from a deep-sea-derived Actinomycete. Org. Lett. 2012;14:3364–3367. doi: 10.1021/ol301343n. - DOI - PubMed
    1. Birch A.J., Wright J.J. The brevianamides: A new class of fungal alkaloid. J. Chem. Soc. D. 1969 doi: 10.1039/c2969000644b. - DOI
    1. Paterson R.R.M., Simmonds M.J.S., Kemmelmeier C., Blaney W.M. Effects of brevianamide A, its photolysis product brevianamide D, and ochratoxin A from two Penicillium strains on the insect pests Spodoptera frugiperda and Heliothis virescens. Mycol. Res. 1990;94:538–542. doi: 10.1016/S0953-7562(10)80017-6. - DOI

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