Chemical constituents of Hypogymnia enteromorpha

Abstract

The lichenHypogymnia enteromorpha (Ach.) Nyl. was sequentially extracted by a solvent series that ranged from non-polar to highly polar liquids. The principal extracellular lichen products isolated from this species were thiophaninic acid, physodalic acid, physodic acid, atranorin, and ventosic acid. The carbohydrate D-arabitol was isolated from the more polar extracts. The isolated constituents were identified by means of mixed melting points, specific color tests, thin layer chromatographic Rf values, infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis. Quantitative estimates of the amounts of these lichen constituents present in the plant are presented. Three components, thiophaninic acid, ventosic acid, and D-arabitol are here reported for the first time to be constituents of this lichen.

Zusammenfassung

Die FlechteHypogymnia enteromorpha (Ach.) Nyl. wurde stufenweise mit mehreren Lösungsmitteln extrahiert, die in ihren Zusammensetzungen von unpolar bis zu hochpolar reichten. Die wichtigsten extrazellularen Produkte, die von dieser Flechtenspezies isoliert wurden waren Thiophaninsäure, Physodalsäure, Physodsäure, Atranorin und Ventossäure. Das Kohlenhydrat D-arabit wurde von den etwas mehr polaren Extrakten isoliert. Die isolierten Bestandteile wurden durch Mischungsschmelzpunkte, spezifische Farbproben, dünnschicht-chromatographische Rf-Werte, Infrarotspektroskopie, NMR-Spektroskopie, Massenspektrometrie und Elementaranalyse identifiziert. Quantitative Bestimmungen erfolgten hinsichtlich der Flechten-Bestandteile. Die drei Verbindungen Thiophaninsäure, Ventossäure und D-arabit werden hier zum erstenmal als Bestandteile dieser Flechte beschrieben.

Résumé

On a soumis le lichenHypogymnia enteromorpha (Ach.) Nyl. à une séquence d'extractions à l'aide d'une série de solvants comprenant des liquides de nature non-polaire jusqu'à très polaire. Les principaux produits extracellulaires de lichen isolés de cette espèce comprennent l'acide thiophéninique, l'acide physodalique, l'acide physodique, l'atranorine et l'acide ventosique. On a isolé l'hydrate de carbone D-arabitol parmi des solvants de haute polarité. L'identification des constituants se fit à l'aide des points de fusions, les épreuves colorimetriques spécifiques, les valeurs Rf de chromatographie sur couche mince, la spectroscopie infrarouge, la spectrometrie de masse et l'analyse élémentaire. Des évaluations quantitatives du niveau de ces composants de lichen présents dans cette plante sont presentées. Trois composés, l'acide thiophaninique, l'acide ventosique et le D-arabitol sont rapportés ici pour la première fois comme constituants de ce lichen.

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Shibamoto, T., Bernhard, R.A. Chemical constituents of Hypogymnia enteromorpha. Plant Food Hum Nutr 24, 199–218 (1974). https://doi.org/10.1007/BF01092736

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Keywords

  • Nuclear Magnetic Resonance
  • Infrared Spectroscopy
  • Nuclear Magnetic Resonance Spectroscopy
  • Magnetic Resonance Spectroscopy
  • Chemical Constituent