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Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus.
J Nat Prod. 2013 Apr 26; 76(4):571-9.JN

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Qi J
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.
Shao CL
No affiliation info available
Li ZY
No affiliation info available
Gan LS
No affiliation info available
Fu XM
No affiliation info available
Bian WT
No affiliation info available
Zhao HY
No affiliation info available
Wang CY
No affiliation info available

MeSH

AnimalsAnti-Bacterial AgentsAntineoplastic AgentsBenzofuransDoxorubicinDrug Screening Assays, AntitumorHL-60 CellsHeLa CellsHumansIsocoumarinsMicrobial Sensitivity TestsMolecular StructureNuclear Magnetic Resonance, BiomolecularOceans and SeasPenicilliumPoriferaStaphylococcus

Pub Type(s)

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

Language

eng

PubMed ID

23477451

Citation

Qi, Jun, et al. "Isocoumarin Derivatives and Benzofurans From a Sponge-derived Penicillium Sp. Fungus." Journal of Natural Products, vol. 76, no. 4, 2013, pp. 571-9.
Qi J, Shao CL, Li ZY, et al. Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus. J Nat Prod. 2013;76(4):571-9.
Qi, J., Shao, C. L., Li, Z. Y., Gan, L. S., Fu, X. M., Bian, W. T., Zhao, H. Y., & Wang, C. Y. (2013). Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus. Journal of Natural Products, 76(4), 571-9. https://doi.org/10.1021/np3007556
Qi J, et al. Isocoumarin Derivatives and Benzofurans From a Sponge-derived Penicillium Sp. Fungus. J Nat Prod. 2013 Apr 26;76(4):571-9. PubMed PMID: 23477451.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus. AU - Qi,Jun, AU - Shao,Chang-Lun, AU - Li,Zhi-Yong, AU - Gan,Li-She, AU - Fu,Xiu-Mei, AU - Bian,Wen-Tao, AU - Zhao,Hong-Ying, AU - Wang,Chang-Yun, Y1 - 2013/03/11/ PY - 2013/3/13/entrez PY - 2013/3/13/pubmed PY - 2013/8/14/medline SP - 571 EP - 9 JF - Journal of natural products JO - J Nat Prod VL - 76 IS - 4 N2 - 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. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/23477451/Isocoumarin_derivatives_and_benzofurans_from_a_sponge_derived_Penicillium_sp__fungus_ L2 - https://doi.org/10.1021/np3007556 DB - PRIME DP - Unbound Medicine ER -