New Rhodomycin Analogs, SS-288A and SS-288B, Produced by aStreptomyces violaceusA262 Mutant

A comprehensive review of glycosylated bacterial natural products

“…Sub-class I contains 365 anthracycline O-glycosides (and a few C-glycosides) bearing variant carbohydrate substitution ranging from mono-to pentasaccharides. C7-and/or C10-Oglycosylation predominates (358 compounds) within sub-class I anthracyclines including D-788, [189][190][191][192][193] oxaunomycins, 193 doxorubicins, 194,195 spartanamicins, 196 daunorubicins, 194,195 daunomycins, 185,197,198 aclacinomycins (aklavins), [199][200][201][202][203][204][205] rhodomycins, 184,[206][207][208][209][210] betaclamycins (and CG-21-C, CG1-C, CG21-B analogs), [211][212][213] auramycins, [214][215][216][217][218][219] MA-144-U and G analogs, [220][221][222] steffimycins, [223][224][225][226] baumycins, 227,228 pyrrocyclines,…”

“…Sub-class I contains 365 anthracycline O -glycosides (and a few C -glycosides) bearing variant carbohydrate substitution ranging from mono- to pentasaccharides. C7- and/or C10- O -glycosylation predominates (358 compounds) within sub-class I anthracyclines including D-788, 189–193 oxaunomycins, 193 doxorubicins, 194,195 spartanamicins, 196 daunorubicins, 194,195 daunomycins, 185,197,198 aclacinomycins (aklavins), 199–205 rhodomycins, 184,206–210 betaclamycins (and CG-21-C, CG1-C, CG21-B analogs), 211–213 auramycins, 214–219 MA-144-U and G analogs, 220–222 steffimycins, 223–226 baumycins, 227,228 pyrrocyclines, 222 rubeomycins, 229,230 pyrromycins, 231 oblemycins (cytorhodins), 232,233 sulfurmycins, 214–219 cinerubins, 188,234–236 mutactimycins, 237–239 alldimycins, 233,240 nocardicyclins, 241 violamycins, 242 ditrisarubicins, 243 aranciamycins, 244–247 A447A∼D1, 248 ciclamycins, 249 isoquinocycline A, 188,250 kosinostatin (quinocycline B), 251,252 isoquinocycline B, 252,253 micromonomycin 254 and other representative anthracyclines. 100,188,201,202,211,229,255–263 Less common sub-class I O -glycoside regioselectivity was observed at C-1 (mutactimycin PR 237,238 ), C-4 [histomodulin, 264 komodoquinone A 265,266 and 4- O -(β- d -glucopyranosyl)-ε-rhodomycinone 267 ], and C-9 (cytorhodins X and Y).…”

Rhodomycin analogues from Streptomyces purpurascens: isolation, characterization and biological activities

“…Its MIC was found to be 2 μg/ml which was comparable to the reported value of 0.5-1 μg/ml (Shoji et al 1968). However, the IC 50 value, around 15 μM (~8 μg/ml) indicating much less toxicity than the reported value of 1 μg/ml (Saito et al 1995). …”

“…The mycelial cake obtained from 200 ml broth was extracted with 100 ml acetone (Saito et al 1995) and the spent broth (200 ml) was extracted with 100 ml chloroform. The acetone extract was concentrated to one-fourth original volume and then reextracted with 25 ml chloroform.…”

Anthracyclines: biosynthesis, engineering and clinical applications

“…9), but which harbor differences in the glycosylation and tailoring patterns have been reported. These include aclacinomycin X ( 30 ), 173 misamycin ( 31 ), 174 rhodomycin derivatives SS-288A ( 32 ) and SS-288B ( 33 ), 175 and two pyrromycins ( 34 , 35 ) (Fig. 9).…”