Akashins A, B, and C: Novel Chlorinated Indigoglycosides fromStreptomyces sp. GW 48/1497

Abstract

Sky blue akashins (see picture) are the first indigoglycosides and the first natural derivatives of 5,5′‐dichloroindigo to be isolated from terrestrial Streptomyces.

Genome Sequence of Marine-Derived Streptomyces sp. Strain F001, a Producer of Akashin A and Diazaquinomycins

“…The marine-derived actinomycete strain F001 is known to produce two compound classes of biomedical interest, the chlorinated indigo glycoside akashin A (1) and several congeners of the diazaquinomycin class of antibiotics (2). Akashin A has demonstrated cytotoxic activity against cancer cell lines (3), whereas it was recently reported that some diazaquinomycin analogs exhibited potent and selective inhibitory activity against a panel of drug-resistant Mycobacterium tuberculosis strains (4).…”

Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

“…On this account are interesting the indigo N-glycosides (blue sugars) 3 , the analogues of naturally occuring akashins 4 showing considerable effect against various human cancer cells. Among other N-glycosidic indole derivatives with promising cancerostatic effects belong staurosporine, K-252d, rebeccamycine and tjipanazoles.…”

Synthesis and Biological Evaluation of Sugar Induced Thiazole Derivatives

“…Some N-glycosides show antineoplastic effects [24]. The indigo N-glycosides (blue sugar), the analogues of naturally occurring akashins [25] showed considerable effect against various human cancer cell. As a review article [26] summarizes the synthesis, structure and evaluation of biological activities of the N-glycosides containing quinazoline skeleton has been published.…”