A yellowish white microneedles, C23H32O14.I1/2 H2O, m.p.262-4o, [alpha]D20 = -71.43o(C=0.42, pyridine), its acetate m.p.123-5o, were obtained in 0.3% yield from the leaves of Chrysanthemum sibiricum FISCHER. This substance is insoluble in water and th...
A yellowish white microneedles, C23H32O14.I1/2 H2O, m.p.262-4o, [alpha]D20 = -71.43o(C=0.42, pyridine), its acetate m.p.123-5o, were obtained in 0.3% yield from the leaves of Chrysanthemum sibiricum FISCHER. This substance is insoluble in water and the usual organic solvents except pyridine and ethylene glycol and, is not decomposed by dilute mineral acids but undergoes decomposition on being boiled in 60% H2SO4 or 35% HCl, giving one mole each of acacetin, glucose and rhamnose. It was not hydrolysed with a rhamnodiastase preparation obtained from the seeds of Rhamnus koraiensis. After permethylation of it, the uncrystallized product was hydrolysed and apigenin-5,4''-dimethyl ether, m.p. 262o was obtained, indicating that the disaccharide residue is at the 7 position of acacetin. Partial hydrolysis of this acacetin-7-rhamnoglucoside in cyclohexanol with formic acid gave acacetin-7-glucoside, m.p. 246o and rutinose, identifying them with authentic specimen on a paper chromatography. It was thus identified as linarin(acacetin-7-rutinoside) by means of mixed fusion, of paper partition chromatography and of its derivatives. Zemplen and Bognar suggsted that the glucosidic linkage of linarin is beta by means of synthesis of this substance. But there is no evidence whether it is hydrolysed by emulsin or maltase or not. Linarin itself was not hydrolysed by an emulsin existing in the seed of Apricot or a maltase, but acacetin-7-glucoside(tilianin) which obtained from linarin gave acacetin and glucose on hydrolysis with the same emulsin and accordingly the glucosidic linkages of linarin and tilianin are thus regarded as beta.