Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025
- PMID: 28218640
- PMCID: PMC5334623
- DOI: 10.3390/md15020043
Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025
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.
Conflict of interest statement
The authors declare no conflict of interest.
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References
-
- Birch A.J., Wright J.J. The brevianamides: A new class of fungal alkaloid. J. Chem. Soc. D. 1969 doi: 10.1039/c2969000644b. - DOI
-
- 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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