A procedure for the absolute identification of anthocyanins: the pigments of blackcurrant fruit

1962 ◽  
Vol 15 (1) ◽  
pp. 114 ◽  
Author(s):  
BV Chandler ◽  
KA Harper

A procedure is outlined for the isolation of pure anthocyanins and their identification without recourse to comparison with reference glycosides. The isolation involves cellulose and polyamide column chromatography and the identification depends on simple but selective oxidative and hydrolytic reactions, adapted to a microscale using paper chromatography. By this method the anthocyanin pigments present in extracts of black currant fruit have been unequivocally identified as cyanidin and delphinidin, their 3-glucosides and 3-rutinosides.

1961 ◽  
Vol 14 (4) ◽  
pp. 586 ◽  
Author(s):  
BV Chandler ◽  
KA Harper

Procedures have been developed for the determination of the type and location of sugar units present in anthocyanins and other flavonoid glycosides. These procedures are based on standard chemical reactions and have been adapted to a microscale using paper chromatography. Individual flavonoids were found to respond variably to enzymic and chemical hydrolyses, which therefore yield information of limited use only. On the other hand, controlled oxidation has been shown to provide information on the type and position of sugar units attached to the flavonoid nucleus. Degradation using peroxide releases the sugars at the 3-position ; permanganate treatment releases sugars attached to readily ruptured cyclic systems ; and ozonolysis releases sugars attached to phenolic and enolic hydroxyl groups. These three techniques, when used together, can result in the absolute identification of anthocyanins and most other flavonoid glycosides.


1963 ◽  
Vol 44 (1) ◽  
pp. 101-106 ◽  
Author(s):  
Wilhelm Dirscherl ◽  
Helmut Thomas

ABSTRACT Perfusion of rat liver with vanillic acid yielded only one metabolite. In paper chromatography with three different solvent systems, the substance showed the same RF-values as vanillyolglycine (3-methoxy-4-hydroxyhippuric acid) and in mixed chromatograms there was only one single spot. After separation by column chromatography, the UV- and IRspectra of the reaction product were identical with those of 3-methoxy4-hydroxy-hippuric acid. During the perfusion experiment, the kinetics of the conjugation were investigated.


1962 ◽  
Vol 39 (3) ◽  
pp. 385-394 ◽  
Author(s):  
Wilhelm Dirscherl ◽  
Helmut Thomas ◽  
Herbert Schriefers

ABSTRACT In rat livers perfused with 3-methoxy-4-hydroxy-mandelic acid, formerly believed to be the endproduct of the metabolism of adrenaline and noradrenaline, three metabolites were detected by paper chromatography. After further purification by column chromatography, one of these substances was identified by melting point, shape of crystals, UV- and IR-spectra as vanillic acid. Perfusion with vanillic acid yielded only one metabolite in very small quantities. Because of its properties it is assumed to be a conjugate of vanillic acid. Hence vanillic acid, isolated in 1959 from human urine by Dirscherl & Schmidtmann, is the actual endproduct of the metabolism of adrenaline and noradrenaline.


1991 ◽  
Author(s):  
Kenneth A. Deffenbacher ◽  
Francis J. Clark ◽  
M. Elizabeth Davis ◽  
Konney J. Larwood

2017 ◽  
Vol 59 (1) ◽  
Author(s):  
Myriam Meléndez-Rodríguez

The preparation of b-phenyl- and  b-(4-chlorophenyl)-g-butyrolactones (<strong>±</strong>)<strong>-3</strong> and (<strong>±</strong>)<strong>-4</strong> and their resolution to the corresponding (+)-(<em>S</em>)-<strong>3</strong>, (-)-(<em>R</em>)-<strong>3</strong> and (+)-(<em>S</em>)-<strong>4, </strong>(<strong>-</strong>)-(<em>R</em>)-<strong>4</strong> through formation, flash column chromatography separation and subsequent hydrolysis of diastereoisomeric 4-hydroxybutyramides (2’<em>R</em>,3<em>S</em>)-<strong>5</strong>, (2’<em>R</em>,3<em>R</em>)-<strong>5</strong>, (2’<em>R</em>,3<em>S</em>)-<strong>6</strong> and (2’<em>R</em>,3<em>R</em>)-<strong>6</strong> is described. The absolute configuration assignment of enantiopure <strong>3</strong> and <strong>4</strong> was supported by X-ray crystallographic structures of (2’<em>R</em>,3<em>R</em>)-<strong>5</strong>,<strong> </strong>(2’<em>R</em>,3<em>S</em>)-<strong>6</strong> and (2’<em>R</em>,3<em>R</em>)-<strong>6</strong>.


2011 ◽  
Vol 78 (3) ◽  
pp. 189-195 ◽  
Author(s):  
Tadeusz Krzaczek ◽  
Monika Gawrońska-Grzywacz

Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of <em>Hieracium pilosella</em> L. Repeated column chromatography, occasionally paper chromatography and recrystallization made the separation of three flavonoid aglycones and six glycosides - possible. Coumarin glycosides were isolated by preparative thin layer chromatography. Subsequent UV, NMR and MS analyses have led to identification of the following flavonoid derivatives: known for the species - apigenin, luteolin, luteolin 7-O- ß-glucopyranoside, luteolin 4’-O-ß-glucopyranoside, isoetin 7-O-ß- -glucopyranoside, isoetin 4’-O-ß-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-ß-glucopyranoside. Third isoetin glycoside contained two different sugar moieties: xylose and glucose, probably attached to the hydroxyl groups at C-4’ or C-4’ and C-2’(or 5’) of an aglycone. Umbelliferone 7-O-ß-glucopyranoside (skimmin) and new for the genus Hieracium esculetin 7-O-ß-glucopyranoside (cichoriin) were determined by NMR and MS methods.


Sign in / Sign up

Export Citation Format

Share Document