title: Naphthablins B and C, Meroterpenoids Identified from the Marine Sediment-Derived Streptomyces sp. CP26-58 Using HeLa Cell-Based Cytological Profiling.
abstract: HeLa cell-based cytological profiling (CP) was applied to an extract library of marine sediment-derived actinomycetes to discover new cytotoxic secondary metabolites. Among the hit strains, Streptomyces sp. CP26-58 was selected for further investigation to identify its cytotoxic metabolites. CP revealed that the known ionophore tetronasin (1) was responsible for the cytotoxic effect found in the extract. Furthermore, three naphthoquinone meroterpenoids, naphthablin A (2) and two new derivatives designated as naphthablins B (3) and C (4), were isolated from other cytotoxic fractions. The structures of the new compounds were elucidated based on analysis of their HRESIMS and comprehensive NMR data. The absolute configurations of the new compounds were deduced by simulating ECD spectra and calculating potential energies for the model compounds using density function theory (DFT) calculations. Compound 1 showed a significant cytotoxic effect against HeLa cells with an IC50value of 0.23 μM, and CP successfully clustered 1 with calcium ionophores.
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Hana
authors.initials: H
authors.lastname: Martucci
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Scott E
authors.initials: SE
authors.lastname: Campit
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Stephanie R
authors.initials: SR
authors.lastname: Gee
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz , 1156 High Street, Santa Cruz, California, 95064, United States.
authors.forename: Walter M
authors.initials: WM
authors.lastname: Bray
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Trevor
authors.initials: T
authors.lastname: Gokey
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: A King
authors.initials: AK
authors.lastname: Cada
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Ten-Yang
authors.initials: TY
authors.lastname: Yen
authors.affiliation: Osaka University of Pharmaceutical Sciences , 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Minoura
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Anton B
authors.initials: AB
authors.lastname: Guliaev
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz , 1156 High Street, Santa Cruz, California, 95064, United States.
authors.forename: R Scott
authors.identifier: 0000-0001-9891-1248
authors.initials: RS
authors.lastname: Lokey
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , 1600 Holloway Avenue, San Francisco, California 94132, United States.
authors.forename: Taro
authors.identifier: 0000-0002-8375-0098
authors.initials: T
authors.lastname: Amagata
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019015:Geologic Sediments / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D015394:Molecular Structure; D009285:Naphthoquinones; D019906:Nuclear Magnetic Resonance, Biomolecular; D013302:Streptomyces / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D009285:Naphthoquinones; D013729:Terpenes; C095338:naphthablin; C000621257:naphthablin B; C000621258:naphthablin C