Sargassopenillines A-G, 6,6-spiroketals from the alga-derived fungi Penicillium thomii and Penicillium lividum

Olesya I Zhuravleva; Maria P Sobolevskaya; Shamil Sh Afiyatullov; Natalya N Kirichuk; Vladimir A Denisenko; Pavel S Dmitrenok; Ekaterina A Yurchenko; Sergey A Dyshlovoy

doi:10.3390/md12125930

Sargassopenillines A-G, 6,6-spiroketals from the alga-derived fungi Penicillium thomii and Penicillium lividum

Mar Drugs. 2014 Dec 9;12(12):5930-43. doi: 10.3390/md12125930.

Authors

Olesya I Zhuravleva¹, Maria P Sobolevskaya², Shamil Sh Afiyatullov³, Natalya N Kirichuk⁴, Vladimir A Denisenko⁵, Pavel S Dmitrenok⁶, Ekaterina A Yurchenko⁷, Sergey A Dyshlovoy⁸

Affiliations

¹ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
² Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
³ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
⁴ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
⁵ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
⁶ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
⁷ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].
⁸ Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russia. [email protected].

Abstract

Seven new 6,6-spiroketals, sargassopenillines A-G (1-7) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR. The absolute configurations of compounds 1, 5 and 6 were assigned by the modified Mosher's method and by CD data. Sargassopenilline C (3) inhibited the transcriptional activity of the oncogenic nuclear factor AP-1 with an IC50 value of 15 µM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Fungi / chemistry*
Furans / chemistry*
Furans / pharmacology*
Magnetic Resonance Spectroscopy / methods
Mice
Penicillium / chemistry*
Phaeophyceae / microbiology*
Spiro Compounds / chemistry*
Spiro Compounds / pharmacology*
Transcription Factor AP-1 / metabolism

Substances

Furans
Spiro Compounds
Transcription Factor AP-1
spiroketal