Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 18, Pages 3751-3757Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300349
Keywords
Natural products; Cytotoxicity; Antibiotics; Biosynthesis; Meroterpenoids
Categories
Funding
- National Institutes of Health (NIH)
- National Cancer Institute, USA [R37 CA044848]
- NOAA [NA100AR4170060]
- U.S. Dept. of Commerce
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The cancer-cell-cytotoxicity-guided fractionation of the acetone extracts of two cultured marine-derived Streptomyces strains belonging to the MAR4 group yielded six new napyradiomycins, compounds A-F (1-6), together with three known compounds, napyradiomycins B2-B4 (7-9). Napyradiomycins 1-4 are new members of the napyradiomycin C-type meroterpenoids, which possess a linear monoterpene bridge between C-7 and C-10a. Compound 4 has an additional tetrahydropyran ring fused to the phenol moiety. Compounds 5-9 are related to the napyradiomycin B-type meroterpenoids. The structures of all new compounds were assigned by interpretation of 1D and 2D NMR, MS, and other spectroscopic data. The relative configurations were assigned based upon interpretation of ROESY 2D NMR experiments. The cytotoxicity of 1-9 against the human colon carcinoma cell line HCT-116 and their antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) are presented.
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