New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities
Anton N. Yurchenko,
Olesya I. Zhuravleva,
Olga O. Khmel,
Galina K. Oleynikova,
Alexandr S. Antonov,
Natalya N. Kirichuk,
Viktoria E. Chausova,
Anatoly I. Kalinovsky,
Dmitry V. Berdyshev,
Natalya Y. Kim,
Roman S. Popov,
Ekaterina A. Chingizova,
Artur R. Chingizov,
Marina P. Isaeva,
Ekaterina A. Yurchenko
Affiliations
Anton N. Yurchenko
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Olesya I. Zhuravleva
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Olga O. Khmel
Institute of High Technologies and Advanced Materials, Far Eastern Federal University, 10 Ajax Bay, Russky Island, Vladivostok 690922, Russia
Galina K. Oleynikova
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Alexandr S. Antonov
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Natalya N. Kirichuk
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Viktoria E. Chausova
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Anatoly I. Kalinovsky
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Dmitry V. Berdyshev
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Natalya Y. Kim
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Roman S. Popov
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Ekaterina A. Chingizova
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Artur R. Chingizov
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Marina P. Isaeva
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Ekaterina A. Yurchenko
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, Russia
Two new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus Penicillium antarcticum KMM 4670, which was re-identified based on phylogenetic inference from ITS, BenA, CaM, and RPB2 gene regions. The absolute stereostructures of the isolated cyclopianes were determined using modified Mosher’s method and quantum chemical calculations of the ECD spectra. The isolation from the natural source of two biosynthetic precursors of cladosporin from a natural source has been reported for the first time. The antimicrobial activities of the isolated compounds against Staphylococcus aureus, Escherichia coli, and Candida albicans as well as the inhibition of staphylococcal sortase A activity were investigated. Moreover, the cytotoxicity of the compounds to mammalian cardiomyocytes H9c2 was studied. As a result, new cyclopiane diterpene 13-epi-conidiogenone F was found to be a sortase A inhibitor and a promising anti-staphylococcal agent.
