Saccharothrixones A–D, Tetracenomycin-Type Polyketides from the Marine-Derived Actinomycete Saccharothrix sp. 10-10

Saccharothrixones A–C (1–3), three new aromatic polyketide seco-tetracenomycins, and saccharothrixone D (4), a new tetracenomycin analogue possessing opposite configurations at all of the stereogenic centers, were isolated from the marine-derived actinomycete Saccharothrix sp. 10-10. Compounds 1–3 r...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2015-09, Vol.78 (9), p.2260-2265
Hauptverfasser: Gan, Maoluo, Liu, Bin, Tan, Yi, Wang, Qiang, Zhou, Hongxia, He, Hongwei, Ping, Yuhui, Yang, Zhaoyong, Wang, Yiguang, Xiao, Chunling
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Sprache:eng
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Zusammenfassung:Saccharothrixones A–C (1–3), three new aromatic polyketide seco-tetracenomycins, and saccharothrixone D (4), a new tetracenomycin analogue possessing opposite configurations at all of the stereogenic centers, were isolated from the marine-derived actinomycete Saccharothrix sp. 10-10. Compounds 1–3 represent the first examples of seco-tetracenomycins where the quinone ring B is cleaved and re-formed into a furanone ring. Their structures were elucidated by spectroscopic analyses and ECD calculations. The absolute configuration of 4 was confirmed by single-crystal X-ray diffraction analysis. Saccharothrixone D (4) showed in vitro cytotoxic activity against the HepG2 cancer cell line with an IC50 value of 7.5 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.5b00577