Biologically Active Quinolinone Alkaloid from Marine Fungus Penicillium polonicum KMM 4719

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Abstract

The marine fungal strain KMM 4719 was isolated from the sea cucumber Apostichopus japonicus and identified as Penicillium polonicum based on three molecular genetic markers: ITS, BenA, and CaM. 3-O-methylviridicatin was isolated from the ethyl acetate extract of the strain culture. 3-O-methylviridicatin demonstrated cardioprotective activity for the first time, as well as urease inhibitory activity (IC50 97.3 μM). In addition, 3-O-methylviridicatin at a concentration of 100 μM (25.1 μg/ml) inhibited the growth of the yeast-like fungus Candida albicans at 23.2%.

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S. S. Starnovskaya

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Author for correspondence.
Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

N. N. Kirichuk

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

V. E. Chausova

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

U. V. Khudyakova

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

E. A. Chingizova

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

A. R. Chingizov

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

A. N. Yurchenko

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

E. A. Yurchenko

G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences

Email: starnovskaya_ss@piboc.dvo.ru
Russian Federation, Vladivostok, 690022

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Supplementary files

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2. Fig. 1. A phylogenetic tree constructed by the ML method based on the combined ITS-BetaCaM sequences, showing the phylogenetic position of strain KMM 4719 among representatives of the genus Penicillium of the Fasciculata section of the Viridicata series. The reliability of the tree was assessed by a bootstrap text of 1000 replicas, the values (%) of which are indicated in the internal nodes. The scale shows the number of nucleotide substitutions per site.

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3. 2. The structural formula of 3-O-methylviridicatin (1).

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4. Fig. 3. Calculated complex of urease (PDB ID 4H9M) and thiourea. The green lines show hydrogen bonds, the yellow hydrophobic interactions between the ligand and the target: (a) general view, (b) enlarged image.

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5. Fig. 4. Calculated complex of urease (PDB ID 4H9M) and 3-O-methylviridicatin (1). The green ones indicate the hydrogen bonds: (a) complex of 3-O-methylviridicatin with amino acid residues of the β domain of urease (ΔG = -6.924 kcal/mol), (b) complex of 3-O-methylviridicatin located between the N-terminal αß and C-terminal (αß)8 TIM domains (ΔG = -6.559 kcal/mol).

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