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Cytotoxic and Antimicrobial Napyradiomycins from Two Marine‐Derived Streptomyces Strains
Author(s) -
Cheng YuanBin,
Jensen Paul R.,
Fenical William
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300349
Subject(s) - chemistry , cytotoxicity , tetrahydropyran , stereochemistry , moiety , antimicrobial , streptomyces , polyketide , staphylococcus aureus , in vitro , bacteria , organic chemistry , biochemistry , ring (chemistry) , biosynthesis , biology , genetics , enzyme
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.