title: Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus.
abstract: Ten new fungal metabolites, including three hydroisocoumarins, penicimarins A-C (1-3), three isocoumarins, penicimarins D-F (6-8), and four benzofurans, penicifurans A-D (11-14), together with four known isocoumarin derivatives (4, 5, 9, 10), were obtained from the sponge-derived fungus Penicillium sp. MWZ14-4, collected from the South China Sea. Their planar structures and relative configurations were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-4 were assigned by the modified Mosher's method and TDDFT ECD calculations together with comparison of their CD spectra. Compound 1 represents a rare naturally occurring isocoumarin derivative with 4-substitution, but no substituent at the 3-position. These compounds were evaluated for antibacterial activities and cytotoxic activities in vitro. Among them, penicifuran A (11) exhibited inhibitory activity against Staphylococcus albus with an MIC value of 3.13 μM.
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Qi
authors.forename: Chang-Lun
authors.initials: CL
authors.lastname: Shao
authors.forename: Zhi-Yong
authors.initials: ZY
authors.lastname: Li
authors.forename: Li-She
authors.initials: LS
authors.lastname: Gan
authors.forename: Xiu-Mei
authors.initials: XM
authors.lastname: Fu
authors.forename: Wen-Tao
authors.initials: WT
authors.lastname: Bian
authors.forename: Hong-Ying
authors.initials: HY
authors.lastname: Zhao
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004317:Doxorubicin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006367:HeLa Cells; D006801:Humans; D049934:Isocoumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D010407:Penicillium / Q000737:chemistry*; D011161:Porifera / Q000382:microbiology*; D013210:Staphylococcus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001572:Benzofurans; D049934:Isocoumarins; C582646:penicifuran A; D004317:Doxorubicin