Electron impact, chemical ionization and field desorption mass spectra of some anthraquinone and anthrone derivatives of plant origin

Evans, Fred J.; Lee, M. G.; Games, David E.

doi:10.1002/bms.1200060903

Cited by 17 publications

(1 citation statement)

References 15 publications

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“…It is unlikely that they are degradation products of flavonoids [69,70] derivative [71,72]. Mass spectra of a series of anthrone glycosides were studied and compared by PROX [73] and EVANS et al [74]. Aloin (= barbaloin), the first crystalline C-glycosyl compound to be isolated as early as in 1851 [5], was characterized structurally in 1952 by MUHLEMANN [71] and shown by chemical synthesis to be 10-C--D-glucopyranosyl-1 ,8-dihydroxy-3-(hydroxymethyl)-9(1OH)-anthracenone (Fig.…”

Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Franz

Grün

1983

Planta Med

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compounds with glucuronic acid have been found in mammals, which are probably analogous to C-glycosylated compounds in plants. C-Glucuronides of drugs in man [10] and other mammals [11, 12] represent a novel type of drug metabolite. As regards the biosynthetic pathway which leads to the formation of the carbon-carbon bond in C-glycosides, very little is known. In some cases it is thought that the attachment of the sugar moiety takes place during an early stage of the aglycone formation but definite proof is still missing and cannot be generalized for all groups of the C-glycosides. The aim of this article is to present a short review of the principal structural features and occurrence of the different classes of C-glycosides and further, to discuss the few biosynthetic findings of the C-glycosyl attachment which have been published so far. C-Glycosyl Flavonoids Chemistry of C-glycosyl Flavonoids As it has been pointed out, this group of C-glycosides has been the subject of a still increasing number of reports, which mainly deal with the occurrence and structural investigation of these compounds. Since they have been the subject of several review articles [3, 6, 7, 13, 14] only the main features are given here. At the present over one hundred C-glycosyl flavonoids have been shown to exist in the plant kingdom. The model compound and one of the first to be isolated was vitexin (8-C-3-D-glucopyranosylapigenm) (Fig. 2), the structure of which was established

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Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Franz

Grün

1983

Planta Med

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The chemical ionization mass spectra of glucosinolates (mustard oil glycosides) and desulphoglucosinolates. A useful aid for structural analysis

Eagles¹,

Fenwick²,

Gmelin³

et al. 1981

Biol. Mass Spectrom.

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The chemical ionization mass spectra of eleven glucosinolates and their related desulphoglucosinolates have been studied. The thermal instability of these compounds prevents the formation of molecular ions, but more intense diagnostic ions are produced under chemical ionization than under electron impact conditions: these facilitate the elucidation of the sidechain structure and hence that of the glucosinolate itself. The method appears suitable for the analysis of simple glucosinolate mixtures, and complements the electron impact mass spectrometric approach described earlier.

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Chemical ionization mass spectrometry of amygdalin with ammonia gas

Cairns¹,

Siegmund²

1982

Biol. Mass Spectrom.

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Under ammonia chemical ionization conditions using the liquid chromatographic moving belt interface for sample introduction, molecular weight information has been observed for the cyanogenic glyceside, amygdalia (D‐mandelonitrile‐β‐D‐glucosido‐6‐β‐D‐glucoside). Additionally, the use of deuterated ammonia has permitted a detailed fragmentation pathway to be outlined via determinations of total acidic hydrogens.

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Electron impact, chemical ionization and field desorption mass spectra of some anthraquinone and anthrone derivatives of plant origin

Cited by 17 publications

References 15 publications

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

The chemical ionization mass spectra of glucosinolates (mustard oil glycosides) and desulphoglucosinolates. A useful aid for structural analysis

Chemical ionization mass spectrometry of amygdalin with ammonia gas

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