Two novel C-glycosides of aureolic acid repress transcription of the MDR1 gene.
In the search for compounds which repress MDR1 gene expression, two novel aryl C-glycosides were isolated from a broth of Streptomyces sp. They had the characteristic structure of a dideoxy-carbohydrate (oliose or olivose) linked directly to chromomycinone, an aglycone of aureolic acids. Further investigation revealed that they were artifacts yielded from an aureolic acid, mithramycin. Acid and methanol were necessary to yield the C-glycosides. This reaction would contribute to the design of useful aryl C-glycosides.
Tagashira
M
M
Foods and Pharmaceuticals Research and Development Laboratory, Asahi Breweries, Ltd., Ibaraki, Japan.
Kitagawa
T
T
Nozato
N
N
Isonishi
S
S
Okamoto
A
A
Ochiai
K
K
Ohtake
Y
Y
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1 / Q000096:biosynthesis / Q000235:genetics*; D002851:Chromatography, High Pressure Liquid; D008956:Models, Chemical; D008926:Plicamycin / Q000031:analogs & derivatives*; D013291:Streptococcus; D014158:Transcription, Genetic / Q000187:drug effects*
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1; D008926:Plicamycin