Microbial glucosidation of 1,2,4-trihydroxy-9,10-anthraquinone (purpurin).
Streptomyces aureofaciens glucosidizes 1,2,4-trihydroxy-9,10-anthraquinone (purpurin) added to the cultivation medium to yield the corresponding 2-beta-D-glucoside. The identity of the glucoside was demonstrated by comparing its physico-chemical properties with data of an authentic sample prepared synthetically. A further chemical glucosidation of the acetylated 2-beta-D-glucoside gives rise to 2-(hepta-O-acetyl-beta-gentiobiosyl)-4-(tetra-O-acetyl-beta-D-gluc opyranosyl) purpurin. All the derivatives are immunoactive.
D000880:Anthraquinones; D055598:Chemical Phenomena; D002621:Chemistry; D005285:Fermentation; D005960:Glucosides / Q000096:biosynthesis; D037102:Lectins / Q000276:immunology / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013304:Streptomyces aureofaciens / Q000378:metabolism*
D000880:Anthraquinones; D005960:Glucosides; D037102:Lectins; C511975:purpurin anthraquinone