Über einen neuen Glykosidtyp der Flavonreihe Mitteilung: Zur Konstitution von Orientosid und Orientin

Hoerhammer, L; Wagner, H.; H, Nieschlag; Wildi, G

doi:10.1002/ardp.19592920710

Cited by 19 publications

(1 citation statement)

References 12 publications

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“…of periodic acid/mol. was incompatible with the structures originally proposed for these compounds (Horhammer, Wagner, Nieschlag & Wildi, 1959). The results suggested further that orientin and isoorientin were isomeric and analyses of the parent compounds and various derivatives supported this view .…”

Section: Discussionmentioning

confidence: 57%

C-Glycosylflavonoids. The chemistry of orientin and iso-orientin

Koeppen

Roux

1965

Biochemical Journal

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1. The structures of orientin and iso-orientin have been investigated by periodic acid and ferric chloride oxidation of the tetra-O-methyl derivatives and by identification of the products of oxidation. 2. The preparation and properties of the 3',4',7-trimethyl ethers of orientin and iso-orientin are described, and the nuclear-magnetic-resonance spectra of orientin, iso-orientin and their tri- and tetra-O-methyl derivatives are discussed. 3. Orientin and iso-orientin are formulated as 8- and 6-C-beta-d-glucopyranosyl-luteolin respectively.

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Section: Discussionmentioning

confidence: 57%

C-Glycosylflavonoids. The chemistry of orientin and iso-orientin

Koeppen

Roux

1965

Biochemical Journal

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Besonderheiten der Zucker von herzaktiven Glykosiden

Reichstein

1962

Angewandte Chemie

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Wenn man die Zuckerkomponenten der digitaloiden Lactone (sowie zweier weiterer kleiner Stoffgruppen) mit denjenigen der übrigen natürlichen Glykoside der höheren Pflanzen vergleicht, so ergeben sich auffallende Unterschiede: Nicht digitaloide Glykoside enthalten als Bausteine fast stets einen oder mehrere der acht Zucker D‐Glucose, D‐Glucuronsäure, D‐Xylose, L‐Arabinose, D‐Galactose, D‐Galacturonsäure, L‐Fucose, L‐Rhamnose. Oligosaccharid‐Anteile enthalten fast stets die Hexose „innen”︁, d. h. direkt an das Aglykon gebunden, Pentosen und Methylpentosen „außen”︁. Oligosaccharid‐Anteile mit mehr als zwei Zuckern scheinen oft verzweigt zu sein. In herzaktiven Glykosiden (und zwei verwandten kleinen Stoffgruppen) kommen von den acht Zuckern nur D‐Glucose und L‐Rhamnose häufig vor. Sehr oft werden zahlreiche andere Zucker gefunden, besonders Hexamethylosen. Oligosaccharid‐Anteile enthalten die Hexose (D‐Glucose) immer „außen”︁. Oligosaccharid‐Anteile mit mehr als zwei Zuckern sind, soweit bekannt, immer linear gebaut.

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Special Properties of the Sugars in Cardioactive Glycosides

Reichstein

1962

Angew. Chem. Int. Ed. Engl.

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Dyes with the radical of 2,4,5-trichloropyrimidine (X) are less reactive than dyes of analogous structure containing the radical of symmetrical trichloropyrimidine (IX). This is due to the fact that, even with a chlorine atom in position 5, the chlorines in positions 2 and 6 of (X) are not as reactive as those at position 4 in (IX), since they lack the enhancing effect of resonance in the pyrimidine ring. moieties almost always contain hexoses "on the inside", i. e. linked directly onto the aglycone, and pentoses and mefhyl pentoses "on the outside". Oligosaccharide moieties containing more than two sugars often appear to be branched. Cardioactive glycosides (and two related minor groups of substances) chiefly contain only two sugars of the eight listed, viz. D-glucose and L-rhamnose. Very often numerous other sugars are found, particularly hexamethyloses. Oligosaccharide moieties always contain the hexose (D-glucose) "on the outside". As far as is known, oligosaccharide moieties with more than two sugars are always built up linearly.

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Über einen neuen Glykosidtyp der Flavonreihe Mitteilung: Zur Konstitution von Orientosid und Orientin

Cited by 19 publications

References 12 publications

C-Glycosylflavonoids. The chemistry of orientin and iso-orientin

C-Glycosylflavonoids. The chemistry of orientin and iso-orientin

Besonderheiten der Zucker von herzaktiven Glykosiden

Special Properties of the Sugars in Cardioactive Glycosides

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